airbnb yacht florida keys

Boat holiday rentals in Florida Keys

Find and book unique boat rentals on Airbnb

Top-rated boat rentals in Florida Keys

Guests agree: these boat rentals are highly rated for location, cleanliness and more.

Boat in Tavernier

Island Sanctuary Islamorada

Stay aboard the eco-friendly two-story 63 ft River Queen with a 360 degree view with beautiful sunrises and sets, mored 1/8 mi offshore in a quite harbor close to shopping center, movie theater, hospital, bars & restaurants. A 10-foot dinghy with small outboard to come & go from shore "ONLY", nowhere else. I also offer Personal Training, deep tissue work & Life Coach sessions. I live on the vessel about a hundred yards from you so if there are any questions, etc. I will be there to assist you.

31 May – 7 Jun

Home in Miami

Luxury Home in Brickell Miami, 5 min to the Beach!

This amazing home situated in a convenient location of Miami, was professionally designed and accommodated to suit your vacation needs. Enjoy our chef inspired large fully equipped kitchen, our ample sophisticated and modern bathrooms, as well as our comfortable bedrooms, upgraded with fine linens and hotel quality mattresses. The Roads is an incredible neighborhood in the limits of Brickell, filled with sidewalks, roundabouts, wide tree lined streets surrounded by tropical native Miami plants.

Apartment in Miami

The Love Lounge Miami Beach & its 420 Friendly

READ THE REVIEWS to see how much of an effort we make to ensure you have the BEST TIME while here. This place is in SOUTH BEACH MIAMI not the venetian causeway. The place has 2 TVs, 2 Queen beds. Prime Location 💯. NO CIGARETTE SMOKING, NO ANIMALS ALLOWED & NO SHOES INSIDE. Keep in mind that other people live within the building, so be aware of the noise but HAVE FUN. This is not a hotel; this is an Air bnb. You will NOT find a better deal on MIAMI BEACH in this area with a host like Vincent.

Boat in Key West

Amazing 4 Bdrm, 4 Bath Catamaran - Purpus

Enjoy all the comforts of home including 4 luxurious staterooms with queen sized beds each with its own private bathroom, a full kitchen with everything needed for on board meal prep, spacious living areas down below and above on the decks. The boat is in great condition and has been well maintained inside and out. Purpus is docked in a first class marina with access to free parking, restaurants, bars, ships store, pools, coffee shop and laundry. Charter options available for additional fee.

Houseboat in Key West

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Make Memories and Enjoy Sunsets on Euphoria

PLEASE READ ALL THE SECTIONS IN THE LISTING. 31ft BOAT ANCHORED at 1.5 mile off Key West NOT IN A MARINA. Transportation to the boat by water shuttle, fee not included in stay. REMEMBER ITS A BOAT, FUN EXCITING, ACCEPTANCE OF TRANSIENCE AND IMPERFECTIONS. THE AESTHETIC IS SOMETIMES DESCRIBED AS ONE OF APPRECIATING BEAUTY THAT IS IMPERFECT, IMPERMANENT AND INCOMPLETE IN NATURE. Embracing simplicity, nature imperfection and find joy, peace that nothing is perfect in this world. Enjoy Life

29 Jun – 6 Jul

Sailboat in Luxury Marina

You will have an unforgettable experience staying on Allora, a 41 ft. sailboat, docked at the Perry Hotel and Marine - a luxury marina. PLEASE VIEW VIDEO BEFORE BOOKING: search "Allora walk through" on youtube Wake up to a freshly brewed cup of coffee and sit in the cockpit watching the sun rise across the water. Swim in the 2 heated, salt water pools and try out one of the many first class restaurants on site. Be sure to take advantage of the free shuttle to old town Key West.

ALL INCLUSIVE! Snorkel/Sail/Spear Fish/Fishing/Fun

You will love staying on this 45' GulfStar Sloop. The boat boasts 2 BR, 1.5 bath with shower, full working galley, A/C throughout and plenty of room to relax down below. Every reservation comes with a sunset sail along with day sailing, snorkeling or fishing. Layout and be lazy on the spacious deck or whatever you would like to do! Visit SailAway GetAways on FB for more detailed view. **Unfortunately one night reservations do not allow time for excursions. Except a sunset sail.**

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

26 Nov – 3 Dec

Boat in Miami

Unique perspective

Experience what its like "living on the hook" as the sailors say or living anchored out in the water. Let the waves rock you to sleep and wake up with the best views of the sun rising above the miami beach skyline to the east and in the evening watch the sun set over downtown miami. You may even see some dolphins! On the 4 of july come to see the fireworks from the boat .great spot to see downtown fireworks .even south beach ones. kayaks available for rent.

26 Feb – 5 Mar

Boat in Fort Lauderdale

Graceland Las Olas Boathouse Treehouse by Beach

A short walk to the beach and downtown, Graceland is where your boat house becomes a tree house on a high tide. This 1979 remodeled vintage double cabin is a hidden gem, an exotic experience for the most sophisticated travelers. Situated conveniently on Las Olas, Grace (formerly Athena) is a short walking distance to the bustling downtown & the sunny beaches of Fort Lauderdale. The boat has 2.5 cabins & 2 full en-suite bathrooms with salt water toilets.

Townhouse in Key Largo

Beautiful Oceanside Mariner's 3 Bedroom Townhome

This marina facing 3 bedroom townhome is spacious and beautifully decorated. Relax with the whole family at this peaceful place to stay. The Oasis pool is probably the nicest pool in Key Largo with Ocean views and beach entrance it is a great spot for any age. Boater's would love this very well maintained Marina. Tennis and Pickle ball on site. Game room for kids and adults to enjoy. Many restaurants, watersports, and excursions nearby.

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for boat rentals in Florida Keys

Family-friendly boat rentals.

Aqua Lodge Houseboat "Starfish"

Last Minute Discount! 48' Yacht & Beautiful Resort

Room in Marathon

Island Yacht Adventures

Place to stay in Key Largo

Luxury Yacht Charter. Lets go cruising!

27 Apr – 4 May

Airbnb Exclusive Offer! 51' Catamaran Yacht

Boat in Key Largo

Yacht/Catamaran ON THE WATER in a Key Largo marina

27 Jan – 3 Feb

Boat in Marathon

Viking Yacht Getaway in the Keys

Luxury 40 ft yacht in paradise awaits you!

26 Sep – 3 Oct

Gonagain! Experience living on the water!

Amazing 33ft sailboat. Sail, stay and play.

Boat in St Key West

Today Is The O'Day!

31 Jul – 7 Aug

NICE BOAT IN THE FL KEYS

Boat in Stock Island

Key West Classic Yacht Charter

Cozy Sailboat + Dinghy For Nature Lovers

Private 45’ Luxury Yacht

Boat in Naples

"Comfort Zone" Private Yacht-Charter

25 Oct – 1 Nov

57ft DeFever in Islamorada Marina

28 Jun – 5 Jul

Luxury Living on the Water

31 Mar – 7 Apr

Miami Yacht Stay Versace Style

28 Feb – 7 Mar

Luxurious 70ft yacht also available for charters

Place to stay in Key West

Eco friendly 46ft fully staffed sailing yacht.

Destinations to explore

• Miami   Holiday rentals
• Miami Beach   Holiday rentals
• Fort Lauderdale   Holiday rentals
• Boca Raton   Holiday rentals
• Key West   Holiday rentals
• Naples   Holiday rentals
• West Palm Beach   Holiday rentals
• Varadero   Holiday rentals
• Havana   Holiday rentals
• Nassau   Holiday rentals
• Sarasota   Holiday rentals
• Anna Maria Island   Holiday rentals
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• Rentals with a sauna   Florida Keys
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• Rentals with a cinema   Florida Keys
• Fitness-friendly rentals   Florida Keys
• Rentals with lake access   Florida Keys
• Rentals with pools   Florida Keys
• Serviced apartment rentals   Florida Keys
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• Campsite rentals   Florida Keys
• Rentals with a firepit   Florida Keys
• Private suite rentals   Florida Keys
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• Rentals with breakfast   Florida Keys
• Cottage rentals   Florida Keys
• Rentals with a hot tub   Florida Keys
• Rentals with a fireplace   Florida Keys
• Waterfront rentals   Florida Keys
• Rentals with a kayak   Florida Keys
• Yurt Rentals   United States
• Yurt Rentals   United Kingdom
• Castle Rentals   United States
• Houseboats   United States
• Holiday Caravans   United Kingdom
• Private Island Rentals   United States
• Farm Houses   United States
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• Cabin Rentals   Australia
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Welcome to Key Lime Sailing Club and Cottages

Your airbnb destination in the enchanting florida keys, key lime sailing club and cottages invites you to experience the authentic charm of key largo, florida. as one of the original airbnbs in the florida keys, we have been providing unforgettable experiences since 1999. choose one of our delightful cottages and embark on a journey like no other..

Endless Adventures Await

Your cottage rental comes with a remarkable bonus – FREE access to an array of thrilling amenities:

• Sailboats : Harness the power of the wind and embark on a sailing adventure like no other.
• Kayaks: Explore the intricate mangroves and uncover hidden wonders.
• Paddle Boards: Glide through the crystal-clear waters and soak in the beauty that surrounds you.
• Snorkel Gear: Dive into a world of vibrant marine life and discover the wonders beneath the surface.
• Fishing Gear: Try your hand at fishing and experience the excitement of reeling in your catch.

A Haven of Relaxation

At Key Lime Sailing Club and Cottages, tranquility is guaranteed. Whether you’re seeking quality time with family, friends, or loved ones, our property offers a serene environment that will rejuvenate your soul. Here’s what awaits you:

• Breathtaking Sunsets: Witness the mesmerizing beauty of Florida Keys’ sunsets right from our docks, creating memories that will last a lifetime.
• Island Exploration: Embark on a captivating journey as you sail to nearby islands, uncovering their secrets and immersing yourself in their natural wonders.
• Kayak the Mangroves: Traverse the peaceful mangrove forests, an experience that will connect you with the pristine beauty of nature.
• Beachside Bliss: Unwind by our tiki hut, feel the tropical atmosphere, and let the gentle wind lull you into relaxation.
• Wildlife Encounters: Encounter friendly Florida manatees and dolphins up close, forming connections with these remarkable creatures.

Experience Excellence

Key Lime Sailing Club and Cottages consistently achieves Superhost status on the Airbnb platform and other sites like Google , Facebook , TripAdvisor , Yelp , etc. Don’t just take our word for it – read the glowing reviews from our satisfied guests and discover why they return year after year.

Conveniently Located for Unforgettable Experiences

Discover the perfect location at Key Lime Sailing Club and Cottages in Key Largo. Just an hour’s drive from Miami, our central position puts you close to local dining, shops, activities, and historical sites. Getting here is a breeze, and once you arrive, prepare for an unforgettable stay. Our dedicated and friendly staff is committed to ensuring your experience exceeds expectations.

Ready to embark on an unforgettable journey? Book your stay at Key Lime Sailing Club and Cottages today and discover why guests rave about their experiences in the Florida Keys. We can’t wait to welcome you to our slice of paradise!

This was my 10th year of staying at KLSC in early March – it continues to be my vacation site of choice – and I’m already in the book or 2016. Great location, amenities and staff. It doesn’t get any better than this.

We had the most wonderful vacation. I want to thank you and your staff. It felt like everyone went out of their way to see our vacation was more then we expected. And it was. If anyone ask me where to go on vacation I only have one answer, “The Key Lime Sailing Club!”

Totally enjoyed our trip,staff was great, my wife had never sailed. She is hooked now, will be back soon, thank you for a great vacation.

Can’t say enough about the staff, perfect! Enjoyed all the watercraft available for use, kids loved the place:) Really enjoyed our stay, Talofa was great, the people and staff really made the trip awesome!

We had an amazing vacation at the Key Lime Club and so much fun sailing in the Keys! The staff were MORE than helpful and so fun to talk with. Loved the relaxed atmosphere, the family feeling at the tiki, and being able to use the water toys was a big plus. Give our love to Captain G, Irene, James and CJ! And thanks again for the sunset sail and the hospitality! We’ll surely recommend the Key Lime Club to others:)

We had a fantastic time. All of the water equipment was awesome! It was so nice not to have to worry about bringing all of that stuff with us. Our home was also equipped with tons of movies and games. What an excellent option for a family to have. Thank you KLSC!

We had a great time at KLSC. The staff was especially wonderful and attentive! We loved it there.

Sailing was great and your staff was very accommodating and top notch.Hello to Capt. G, Irene and Jeff

Perfect for our family vacation. Not over commercialized and a great place to get outside and discover things! Out boys loved it.

We were so pleasantly surprised at Key Lime North! Breathtaking, beautiful, and very hard to leave! Sandra, Nick, and Heather were wonderful, helpful, and will be our lifetime friends. Paulie made everything special including remembering birthdays and beyond! Captain Sheldon was a fantastic sailing instructor. Nothing beats this vacation!

We LOVED our stay and your hospitality. Everyone went above and beyond to make the stay enjoyable, including John from Michigan who took us out in his sailboat one afternoon. That was definitely our treasure of the week, spending time visiting with him while sailing. Diamond in the rough, so glad we stayed! Definitely would book here again if the Keys were our destination.

We Still Have Cottages Available, Request to Book!

Florida Keys vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Florida Keys

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Tiny home in Cutler Bay

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Oct 20 – 27

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Romantic Retreat is an Historic, free standing cottage which, in the 1800's, was the cistern for the Cigar Maker cottages here. It is decorated in a light Caribbean motif, efficiency kitchen (frig, microwave, hot plate) and a very airy bathroom with tub/shower. King memory foam bed and sleeps 2 persons only. 32” Smart TV (bring your Netflix, Amazon UN/PW's). Bose Bluetooth speaker, Amazon Alexa provided. A private adjacent deck with a 2 person Solana spa/seating. Also handicapped accessible.

Guest suite in Marathon

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Jul 30 – Aug 6

Vacation home in Key Largo

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

Condo in Key Colony Beach

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Home in Marathon

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Aug 24 – 31

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Apartment in Key West

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Cottage in Miami Lakes

* Lake Cottage * SpaLike Bath *

The cottage is centrally located in the serene hidden gem of Mia Lakes. Perfect for couples, solo adventurers or business travelers. You will feel hidden away from it all but yet only 5- 10 min walk from restaurants, shopping, groceries, movie theater, spa, gym etc. Our lakefront guest cottage is surrounded by lots of native plants, trees & wild life. You may swim, fish (catch & release) on the lake, as well as use of a paddle board & kayak.

Aug 23 – 30

Dolphin Drive

Spacious, fun unit with private entrance and large living room with kitchen, bedroom and bathroom (Sleeps up to 4). Game room/living room includes billiards, ping pong and darts. Room for your boat trailer and vehicle in long, private driveway. 2/10 of a mile from the public boat ramp.

Jun 19 – 26

Condo in Key West

Beach Club Ocean Front 2BR Condo

Come fall in love with Key West in our luxurious ocean front condo. The Key West Beach Club is located directly on the Atlantic in a quiet residential secured building. It is a 2BR, 2 1/2 Bath located in Mid-Town.

Sep 18 – 25

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Florida Keys vacation rentals

Other great vacation rentals in florida keys.

Guest suite in Tavernier

POOL ! Key Largo! Tavernier! Welcome to Paradise!

Oct 18 – 25

Cottage in Key Largo

Charming Key Largo Cottage on the Water w/Kayaks!

Oct 22 – 29

Home in Key Largo

Your Keys Getaway!

Jan 21 – 28

Cottage in Islamorada

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Sep 28 – Oct 5

Charming Waterside Cabana in Key Largo | Cabana 4

Jun 23 – 30

Apartment in Key Largo

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Guesthouse in Key Largo

Oceanside, 1 bedroom, Bungalow in Key Largo

Mar 12 – 19

Marathon one-level home on the Marina - with slip!

Private Florida Keys vacation rentals

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

Guest suite in Key Colony Beach

Turtle-By-The-Sea: the Best Deal in KCB!

Sep 17 – 24

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Mar 19 – 26

The Paradise 2

Home in Key Colony Beach

Coral House: 2/2 Waterfront in KCB w/ King Beds

May 11 – 18

Aug 31 – Sep 7

Beach House, Private Pool & Dock, Gulf Sunset view

Dec 14 – 21

Little Cottage on an island

Jul 18 – 25

Florida Keys home rentals

Key Largo Waterfront Home with Tiki & Boat Dock

Sep 26 – Oct 3

Florida Keys Oceanside Utopia

Jan 11 – 18

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Oct 26 – Nov 2

Waterfront Private Home w/Pool-Family&Pet Friendly

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

Nov 10 – 17

Home in Upper Sugarloaf Key

Bungalows at Sugarloaf Beach - The Lighthouse

Private 1 Acre House~Private Beach~Tiki Hut~Dock

Oceanfront *PARADiSE* Amazing views, pool, dock

Your guide to Florida Keys

All about the florida keys.

From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.

The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.

The best time to stay in a vacation rental in Florida Keys

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.

Top things to do in Florida Keys

Duval street.

Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.

Dry Tortugas National Park

Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.

Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.

Destinations to explore

• Miami   Vacation rentals
• Miami Beach   Vacation rentals
• Fort Lauderdale   Vacation rentals
• Boca Raton   Vacation rentals
• Key West   Vacation rentals
• Naples   Vacation rentals
• West Palm Beach   Vacation rentals
• Varadero   Vacation rentals
• Havana   Vacation rentals
• Nassau   Vacation rentals
• Sarasota   Vacation rentals
• Anna Maria Island   Vacation rentals
• House rentals   Florida Keys
• Hotel rentals   Florida Keys
• Townhouse rentals   Florida Keys
• Monthly Rentals   Florida Keys
• Rentals with beach access   Florida Keys
• Condo rentals   Florida Keys
• RV rentals   Florida Keys
• Pet-friendly rentals   Florida Keys
• Houseboat rentals   Florida Keys
• Rentals with an accessible height bed   Florida Keys
• Kid-friendly rentals   Florida Keys
• Tiny house rentals   Florida Keys
• Rentals with an EV charger   Florida Keys
• Rentals with a washer and dryer   Florida Keys
• Guesthouse rentals   Florida Keys
• Rentals with an accessible height toilet   Florida Keys
• Smoking-friendly rentals   Florida Keys
• Beach house rentals   Florida Keys
• Villa rentals   Florida Keys
• Apartment rentals   Florida Keys
• Wheelchair accessible rentals   Florida Keys
• Resort rentals   Florida Keys
• Bungalow rentals   Florida Keys
• Bed and breakfasts   Florida Keys
• Rentals with a sauna   Florida Keys
• Beach condo rentals   Florida Keys
• Boat rentals   Florida Keys
• Family-friendly rentals   Florida Keys
• Rentals with outdoor seating   Florida Keys
• Mansion rentals   Florida Keys
• Rentals with a home theater   Florida Keys
• Fitness-friendly rentals   Florida Keys
• Rentals with lake access   Florida Keys
• Rentals with pools   Florida Keys
• Serviced apartment rentals   Florida Keys
• Rentals with a patio   Florida Keys
• Campsite rentals   Florida Keys
• Rentals with a fire pit   Florida Keys
• Private suite rentals   Florida Keys
• Boutique hotel rentals   Florida Keys
• Beachfront rentals   Florida Keys
• Rentals with breakfast   Florida Keys
• Cottage rentals   Florida Keys
• Rentals with a hot tub   Florida Keys
• Rentals with a fireplace   Florida Keys
• Waterfront rentals   Florida Keys
• Rentals with a kayak   Florida Keys
• Yurt Rentals   United States
• Yurt Rentals   United Kingdom
• Castle Rentals   United States
• Houseboats   United States
• Holiday Caravans   United Kingdom
• Private Island Rentals   United States
• Farm Houses   United States
• Farm Cottages   United Kingdom
• Cabin Rentals   Australia
• Luxury Cabins   United Kingdom
• Luxury Cabins   United States
• Holiday Chalets   United Kingdom
• Cottage Rentals   United States
• Holiday Cottages   United Kingdom
• Mansion Rentals   United States
• Villa Rentals   United Kingdom
• Holiday Bungalows   United Kingdom
• Bungalow Rentals   United States
• Condo Rentals   United States
• Holiday Apartments   Australia
• Holiday Houses   United States
• Holiday Houses   United Kingdom
• Private Holiday Rentals   United Kingdom
• Big House Rentals   United States
• Big Cottages   Australia
• Large Villas   United Kingdom
• House Rentals with a Pool   United States
• Cabin Rentals with a Pool   United States
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Home » North America » 15 of the Best Airbnbs in Florida Keys: My Top Picks

15 of the Best Airbnbs in Florida Keys: My Top Picks

The most southerly point of the United States, Florida Keys could be another country. One hundred islands made up of sandbars and mangroves welcome gently lapping turquoise waves onto their white sands. The flat, calm waters mean it’s the perfect place to go stand up paddle boarding or kayaking for lazy days hopping between the islands!

After a day of paddling or swimming, you’ll need somewhere to come back to. Why not take a look at vacation rentals in the Florida Keys? These can be anything from your own apartment in a condo to a yacht. They’re the perfect way to get a local feel for this stunning part of the world.

With that in mind, we’ve put together this list of the best Airbnbs in Florida Keys, curated by travel style, budget, and location. There are also some awesome Airbnb Experiences, so you can have a blast when you’re there. Let’s check it out!

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Quick Answer: These are the Top 5 Airbnbs in Florida Keys

What to expect from airbnbs in florida keys, the top 15 airbnbs in florida keys, more epic airbnbs in florida keys, what to pack for florida keys, final thoughts on florida keys airbnbs.

Bella Vita Condo steps from Duval

• > Wrap-around porch with chairs
• > Self-check-in

Unique Camping Shed near beach

• > Kayak campfire stargazing evenings

Multi-Million Beach Mansion with pool

• > $$$$$$$$$$$$$
• > 10 Guests
• > Private beach
• > Oceanfront heated pool

Key West Cozy Home

• > Awesome location
• > Kayaks and paddle boards for rent

Mallory House Room

• > Dedicated workspace
• > Close to cafes and restaurants

From one of the best US National Parks , the Everglades to Key West, the most southwesterly point, it’s more than two hours by car (about 100 miles). So, location is important here.

With your own transport (maybe even get an RV rental?), the Keys are pretty easy to navigate, so it’s not the end of the world if you’re a little journey from your desired destination.

The next thing to take into consideration is cost. Florida Keys isn’t cheap; however, because Airbnbs offer great value for money, you can be assured that every dollar you spend goes towards a high-quality vacation rental, whether that’s a classy condo, a quirky tiny house, or a luxury yacht.

Many vacation rentals in Florida Keys are professionally managed through companies. However, you will find a few properties where you’ll be welcomed by a local host.

Florida Keys is a narrow strip of land surrounded by the sea. Since you’re never more than a few minutes from the water, why not stay on a boat? A boat could be anything from a small vintage sailboat to an ultra-luxurious mega yacht.

If you’re planning a group celebration, a villa is a great option. These large properties often have multiple bedrooms and living spaces indoor and out, so they’re ideal for families.

Condos (or condominiums) are like apartments, but a little different. If you’re from the United States, they’ll need no further explaining. You may even live in one! However, for travellers from the rest of the world, they’re a large building where you own or rent the living area of your building but share common areas.

Now you know what to expect and why you should choose vacation rentals, let’s get to the part you’ve all been waiting for. Here are 15 of the coolest Airbnbs in Florida Keys. You’re going to love them!

Bella Vita Condo steps from Duval | Overall Best Value Airbnb in Florida Keys

Ideal for couples, this colourful property is a great value Airbnb in Key West. It’s less than half a block from Duval Street, and many other landmarks are within a stone’s throw. Back in the flat, you’ll be treated to bright decor, a king bed, flat-screen smart TVs, and a cosy living area. Enjoy your morning coffee on the porch and watch the world go by!

This spot has one of the best locations in Florida Keys – just half a block from Duval Street! The king bed makes it perfect for couples, who can spend the morning enjoying a coffee and people-watching from the porch.

Unique Camping Shed near beach | Best Budget Airbnb in Florida Keys

The Florida Keys are a lot of things, but cheap isn’t one of them . However, with some research, you can find affordable properties, such as this tiny house in Key Largo. Offering a glamping experience, there’s a king bed in the hut and a small outdoor space. Your host offers kayak campfire stargazing experiences too, so get in touch with them if you’d like to know more.

We’ve tested countless backpacks over the years, but there’s one that has always been the best and remains the best buy for adventurers: the broke backpacker-approved Osprey Aether and Ariel series.

Want more deetz on why these packs are so  damn perfect? Then read our comprehensive review for the inside scoop!

Multi-Million Beach Mansion with pool | Over the Top Luxury Airbnb in Florida Keys

This place is just insane. You have your own private beach overlooking Summerland Key! Not only that, there’s a heated pool right by the ocean, a pool table, and a hammock. This place is perfectly set up for you to chill out and escape the real world. There’s space for up to ten guests, so it’s good for families and friends. We’re sure you’ll spend all your time outside, but it’s good to know there’s a 56-inch curved TV waiting for you in the living room.

Key West Cozy Home | Perfect Airbnb for Solo Travellers

Home stays are a great option for solo travellers. They not only allow you to save some cash, but also to have a completely local experience during your stay. At this family home on Stock Island (near Key West), there are kayaks and paddleboards for rent, and you’re welcome to use the communal areas of the house. Did we mention the home is right on the water?!

Mallory House Room | Perfect Airbnb for Digital Nomads

Being a digital nomad is becoming more and more common. All you need is a laptop, somewhere to work, and fast Wi-Fi. If you supply the laptop, Mallory House will give you the other two ingredients. This boutique hotel is close to the cafes of Key West, so if you fancy a change of scenery for the day, it’s easy to get one. When you’re chilling at the guest house, be sure to take your hosts up on their offer of a complimentary coffee overlooking Duval Street.

Stash your cash safely with this money belt. It will keep your valuables safely concealed, no matter where you go.

It looks exactly like a normal belt  except for a SECRET interior pocket perfectly designed to hide a wad of cash, a passport photocopy or anything else you may wish to hide. Never get caught with your pants down again! (Unless you want to…)

Here are a few more of my favorite Airbnbs in Florida Keys!

Romantic Retreat with private deck | Best Short Term Rental for Couples

This cute, free-standing cottage dates back to the 1800s and is the perfect romantic Airbnb for a couple. Not only does it have a king bed inside, but there’s a rocking love seat on the private deck as well as a table and chairs – and a private hot tub! There are also heated swimming pools on the property that you’re welcome to use.

Tropical family-friendly home | Best Airbnb in Florida Keys for Families

Another property close to Duval Street in Key West, this Airbnb is perfect for families. There’s room for up to eight guests across three bedrooms, with singles and sofas in the smaller room perfect for children. With a fully equipped kitchen, you can save a few dollars over eating out, and there’s free parking on the driveway, too. You can even bring your furry friend as pets are welcome!

Floating Tiny House – 70’s sailboat | Best Boat in Florida Keys

This renovated 25-foot sailboat hails from 1978 and is packed with retro charm. It’s docked in Stock Island marina, so as well as your cute boat, you’ve got access to the Perry Hotel. Here, there’s a bar, gym, restaurants, pools, and even dog parks! The boat, named Poppy, is quite small. It’s ideally suited to a solo traveller, or it could be a romantic retreat for a couple.

Four bedroom villa on Duck Key | Best Villa in Florida Keys

Duck Key is about halfway down Florida Keys, and there are some pretty awesome villas here – such as this one. Another property ideal for families, four bedrooms can sleep up to ten guests, there’s a fully equipped kitchen and a swimming pool. As well as free parking, you can take advantage of a 35-foot dock to moor a boat.

Affordable Beachfront Luxury sleeps six | Best Condo in Florida Keys

Back in Key West, you’ll find this cool condo close to Smather’s Beach. The large indoor space boasts a kitchen, sitting area, and three bedrooms, but it’s the shared spaces that make this place special. You’ve got access to an Olympic sized swimming pool and hot tub right by the beach! Prefer to stay dry? Make use of the grilling area and covered picnic areas and enjoy some lunch. Go on, treat yourself!

Stars and Stripes Lifeguard Tower | Most Unique Airbnb in Florida Keys

Always dreamed of appearing in Baywatch? That may never happen, but you can pretend when you’re staying in this lifeguard tower! Located at the very north of the Keys in Key Largo, it offers easy access to the Everglades too. Breakfast is included in this no-frills accommodation, and it’s sure to make memories that last far beyond your flight (or drive) home.

Casa Loca | Best Airbnb in Key West

A lot of the Airbnbs we’ve seen so far are in Key West, and that’s no surprise; it’s the most popular location in the Keys! It’s probably got the biggest selection of accommodation, but here’s one more we think you’ll love. Boasting a private heated pool and concierge service, this luxurious retreat is ideal for a family or group of friends. It’s usually booked, so move fast!

Two bedroom condo for four | Best Airbnb in Islamorada

Islamorada and Tavernier are closer to the north end of the Keys, and they’re much quieter than Key West. For some, that might be a big attraction. This condo has room for four guests across two rooms, so it could suit a small group or a couple. You have access to a cafe, a large heated pool, and spectacular ocean views from here.

Charming Key Largo Cottage | Best Airbnb in Key Largo

Another Key Largo Airbnb, this cute cottage is right on the water and comes with kayaks and paddleboards. The tiny house cleverly uses space to make room for up to four guests in a studio style room in an RV park. The cottage has a fully equipped kitchen stocked with a coffee maker and other useful appliances.

Fully furnished efficiency studio | Best Airbnb in Marathon

Last but not least is this small cottage by the ocean in Marathon. It’s great for solo travellers or couples on a budget. The studio-style apartment comes with a fully equipped kitchen, queen bed, and an open plan living space. Outside, you can chill out at the picnic table and enjoy a meal under the stars in the evening!

Pants, socks, underwear, soap?! Take it from me, packing for an Airbnb stay is not always quite as straightforward as it seems. Working out what to bring and what to leave at home is an art I have perfected over many years.

Snoring dorm-mates can ruin your nights rest and seriously damage the hostel experience. This is why I always travel with a pack of decent ear plugs.

Hanging Laundry Bag

Trust us, this is an absolute game changer. Super compact, a hanging mesh laundry bag stops your dirty clothes from stinking, you don’t know how much you need one of these… so just get it, thank us later.

Sea To Summit Micro Towel

Hostel towels are scummy and take forever to dry. Microfibre towels dry quickly, are compact, lightweight, and can be used as a blanket or yoga mat if need be.

Monopoly Deal

Forget about Poker! Monopoly Deal is the single best travel card game that we have ever played. Works with 2-5 players and guarantees happy days.

Grayl Geopress Water Bottle

Always travel with a water bottle! They save you money and reduce your plastic footprint on our planet. The Grayl Geopress acts as a purifier AND temperature regulator. Boom!

Don’t Forget Your Florida Keys Travel Insurance

ALWAYS sort out your backpacker insurance before your trip. There’s plenty to choose from in that department, but a good place to start is Safety Wing .

They offer month-to-month payments, no lock-in contracts, and require absolutely no itineraries: that’s the exact kind of insurance long-term travellers and digital nomads need.

SafetyWing is cheap, easy, and admin-free: just sign up lickety-split so you can get back to it!

Click the button below to learn more about SafetyWing’s setup or read our insider review for the full tasty scoop.

So, there you have it. Those are the 15 best Airbnbs in Florida Keys, with some really cool Airbnb Experiences thrown in too. Whether you want to stay in a tropical villa with a pool, a cool condo, or even a tiny house lifeguard tower, there’s an Airbnb in Florida Keys for you.

Still can’t make your mind up? Well, let us round off with reminding you of our overall best value Airbnb in Florida Keys. That’s the Bella Vita Condo steps from Duva l. Located just steps from the Key West Historic District, it has awesome reviews, and you’re sure to love it.

We hope that wherever you choose to stay in Florida Keys, you have a fantastic vacation. To keep yourself and your belongings safe, make sure you check out World Nomads for travel insurance!

• Check out our Backpacking USA guide for in-depth info for your trip.
• Use our Where to Stay in Florida Keys guide to plan your adventure.
• Backpackers and frugal travellers can use our budget travel guide.
• Make sure you visit the other best places in the USA too.
• That will of course include many of the stunning National Parks of Florida .
• A great way to see the country is by taking an epic road trip around Florida .

Colleen Kinsey

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Holiday rentals in Florida Keys

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Florida Keys

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest suite in Homestead

Honeymoon Suite~Beach essentials & free parking

🌴Come and relax in our clean and cozy private guest suite, nested within a beautiful and safe gated community. Located just north of Key Largo, near Everglades National Park and Biscayne National Park. Whether you plan on exploring the fun city of Miami or enjoy the gorgeous Florida Keys, you will be in a great central location! Our guest suite has a luxurious and comfortable bed, high end amenities and a Smart TV. Everything you need to unwind, relax and recharge after a fun day of exploring! 😴

Tiny home in Cutler Bay

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Home in Key Colony Beach

Coral House: 2/2 Waterfront in KCB w/ King Beds

Dog-friendly canal-front home with waterfront patio, water views, king size beds, & a washer/dryer! Welcome to the heart of the Florida Keys. Come relax, play, and stay in Key Colony Beach. Our house is perfect for families, couples, & small groups looking to experience the Keys. Walk to nearby atttractions such as dining, live music, water sports rentals, marinas, fishing charters, private boat rentals, shopping, and more. Have a small boat or jet ski? We have a 20 foot dock that you can use.

Guest suite in Marathon

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Home in Key Largo

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Cottage in Key Largo

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Lookout Point is Wide open breathtaking Water View , Amazing Sunrises with a cup of Morning coffee, Refreshing breeze, Sound of water and Rustle of palm trees will start your day… Fishing right from the property, Kayaking. Taking sunbath on Chaise lounges or Reading books or just sitting under Tiki having a nice conversations and enjoying beautiful scenery of the view. You will see fishes jumping out of water, seagulls trying to catch up it , you might see manatee swimming by or dolphins.

Apartment in Key Colony Beach

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

26 Nov – 3 Dec

Guest suite in Key Colony Beach

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

Home in Marathon

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Cottage in Miami Lakes

* Lake Cottage * SpaLike Bath *

The cottage is centrally located in the serene hidden gem of Mia Lakes. Perfect for couples, solo adventurers or business travelers. You will feel hidden away from it all but yet only 5- 10 min walk from restaurants, shopping, groceries, movie theater, spa, gym etc. Our lakefront guest cottage is surrounded by lots of native plants, trees & wild life. You may swim, fish (catch & release) on the lake, as well as use of a paddle board & kayak.

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Florida Keys holiday rentals

Other great holiday rentals in florida keys.

Beach House, Private Pool & Dock, Gulf Sunset view

29 Mar – 5 Apr

The Gulf Cottage at Marathon Key

25 Jul – 1 Aug

Little Cottage on an island

Boat in Key West

Sailboat in Luxury Marina

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Apartment in Key West

Hidden Beach unit 1 The Perfect Place to stay

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

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12 Incredible Airbnbs in the Florida Keys

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The Florida Keys are a string of tropical islands off the southern tip of Florida . Known for its tropical atmosphere, gorgeous sandy beaches, fantastic seafood, and incredible marine adventures, the Keys have become one of the most popular vacation destinations in the United States. In addition to all the marine attractions, you can also visit many historical places to learn about the island’s history and culture. The Florida Keys are the perfect sun-soaked destination to escape the cold!

You won’t be short of incredible options of places to stay in the Florida Keys. The region is full of unique Airbnbs and vacation homes to choose from. With everything from houseboats to historic homes, it can be hard to pick the best one! A stay at one of the incredible Airbnbs below will make your trip that much more special.

Check out our list of 12 amazing Airbnbs in the Florida Keys so you can spend less time planning and more time on the beach!

Disclaimer: This post may contain affiliate links. If you make a purchase or booking through one of our links we may earn a small commission (don’t worry, it’s at no extra cost to you).

Top 10 Things To Do in the Florida Keys

• Walk Duval Street and explore the many museums, souvenir shops, galleries, and cafés. This is a great place for nightlife and people-watching!
• Visit the former home of author Ernest Hemingway in Key West. You can take a tour of the inside of the house, which is furnished with many of the original pieces.
• Go fishing in Marathon , the commercial and sportfishing center of the Middle Keys.
• Visit Crocodile Lake National Wildlife Refuge , which protects the last remnants of the American crocodile’s natural habitat.
• Explore Dry Tortugas National Park . It’s a combination of history and an incredible underwater world full of marine life including sharks, sea turtles, and tropical reef fish.
• Visit Fort Zachary Taylor Historic State Park to learn about the history of Fort Taylor and its part in the Civil War. 
• Discover the marine life of John Pennekamp Coral Reef State Park , the first underwater protected park in the US. It’s a great place to go snorkeling or scuba diving.
• Rent kayaks or SUP boards and explore the waters of Key West at your own speed. Many Florida Keys Airbnbs come with these included in the rental!
• Take a tour of the Sea Turtle Hospital for a behind-the-scenes look at the facilities and rehabilitation process that is helping to restore the sea turtle population of Key West.
• Head to the southernmost tip of the continental USA and take an insta-worthy picture with the monument.

Why Stay in an Airbnb in the Florida Keys

Staying in an Airbnb in the Florida Keys has plenty of benefits. First, you’ll get to choose the exact location you want to stay in – whether that’s right in the heart of the action around Duval Street in Key West or away from the crowds in your own private oasis.

The selection of Airbnbs in the Florida Keys is extensive. You can stay in a floating house on the water, an adorable cottage, or a luxurious waterfront villa. Plus, Airbnbs offer lots of extra amenities that most hotels don’t – pools, hot tubs, and kayaks are just the beginning.

By choosing to stay in an Airbnb you are likely to get far more value than staying at a hotel. Most of the Florida Keys vacation homes are much nicer and more spacious than your average hotel room. And if you are traveling as a large group, an Airbnb will likely cost less per person than paying for multiple hotel rooms. 

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The 12 Best Airbnbs in the Florida Keys

Best florida keys airbnbs for couples and solo travelers, 1. totally unique floating tiki house in key west.

If you’re looking for a unique place to stay in the Florida Keys, then look no further! Taking the best parts of boat life and combining them with the space and comforts of home, The Tiki Suite is the ultimate glamping experience.

This tropical-themed floating home sits right on the water. There’s gorgeous Brazilian hardwood flooring throughout the home that adds a touch of luxury, along with high vaulted ceilings that make this minimal space feel more spacious. The bedroom has a comfortable king-sized bed with french doors that open up to the ocean. Don’t worry about being too hot here, as the structure has been designed to promote maximum cooling efficiency.

Relax in the hammock while enjoying the sounds of the ocean, or make use of the stand-up paddleboards and snorkel gear to explore underwater. This home is a dream for wildlife lovers, with the chance to see some of Florida’s incredible marine life including dolphins, manatees, stingrays, conch, and starfish.

This Florida Keys Airbnb is anchored out in the harbor away from land, so it’s an ideal place for those looking for a true escape. It can be easily accessed using a local water taxi so you can head to Key West and explore the many attractions there.

2. Romantic Studio on the Water on Key Largo

Perfect for a romantic getaway, this beautifully upgraded studio has scenic views of Manatee Bay and comes stocked with all the amenities you will need for a wonderful vacation.

This studio apartment is immaculately clean and tastefully decorated with modern furniture. Relax with a glass of wine on the sofa, or step outside onto the balcony to enjoy the scenic ocean views at sunset. You may even spot manatees and other marine life that frequent the area. Even better, you can go fishing on the dock outside and grill up your catch of the day on the outdoor BBQ!

If you want to stay active on your vacation, you’ll be happy to know that this Airbnb comes with access to kayaks and paddleboards as well as an outdoor community pool. It’s in Manatee Bay Marine in Northern Key Largo, just 10-15 minutes from local beaches, state parks, bars, and restaurants. 

3. The Southern Cross: 32-Foot Sailboat in Key West

Have you ever dreamed of living on a sailboat? This amazing Florida Keys Airbnb gives you a chance! Located in the marina community of Key West Harbour, you’ll love the stunning views of the Atlantic ocean and having access to high-end resort facilities.

The inside of this 32-foot Morgan Sailboat is gorgeous with teak and mahogany wood throughout. All the amenities you need for a comfortable stay are here including a small kitchen, a bathroom with shower, a comfortable bedroom, plus a TV, AC, and access to hot and cold water. Of course, if you want more space, you can always walk over to the marina clubhouse. 

As a guest here, you’ll have access to the marina’s high-end resort facilities. These include a restaurant and bar, a pool, a private sandy beach, a fitness center, a sauna, free kayak rentals, and an oceanside tiki hut.

This Airbnb is surrounded by nature in a quiet marina where you can enjoy watching sunsets from the deck and looking out for marine life. If you’re in the mood to head out on the town, downtown Key West is just 3 miles away.

4. Renovated Cottage with Hot Tub

This adorable Key West cottage is just a half-block away from Duval Street so restaurants, art galleries, and shops are right outside your door! It dates back to the 1800s, when the building was used as a cistern. Since then, it has been completely renovated with modern amenities. 

The interior has light Caribbean decor which gives it a relaxing atmosphere. It’s a studio-sized apartment with a king memory foam bed, so this Airbnb would be a perfect choice for couples or solo travelers. 

You’ll love the private deck with a table, chairs, and a rocking loveseat. Enjoy a drink here at sunset while you play your favorite music over the Bose Bluetooth speaker.

As a guest here, you’ll also have access to two heated pools and a Weber grill if you want to make meals at home. But why bother when there are so many amazing restaurants nearby? 

Check Price & Availability on VRBO

Best Florida Keys Airbnbs for Small Groups and Families

5. tranquilo: luxury houseboat in key west.

If you’ve ever wanted to live on a houseboat, this Florida Keys Airbnb is for you! This three-story luxury houseboat has incredible ocean views and ample space for 6 guests. 

Two queen bedrooms are on the 1st floor, including the master stateroom which features granite counters, a maple-built-in dresser, a 42″ TV, and floor-to-ceiling windows. Throughout the home is soft lighting that creates a soothing ambiance.

An indoor spiral staircase leads you to the 2nd floor where there’s a spacious living room with a sectional sofa and 56″ 4K HD TV. If you need extra space, this couch converts into another queen-sized bed. This room opens up to an exterior 2nd level deck with a gorgeous view of the harbor and cushioned seating for 6.

The best part about this unique Florida Keys Airbnb is the massive 450-square-foot sun deck on the top floor with cushioned seating for 10 and a round daybed. You’ll love hanging out here and watching the beautiful sunsets of Key West. The top floor also has a full kitchen with a double sink and all the appliances you need to cook, but you’ll likely want to grill on the outdoor BBQ!

The boat is docked at the Yacht Club so you’ll have access to amenities including a private beach, a pool, a gym, a restaurant, a bar, and an oceanside tiki for entertaining. Even though you’ll be right on the water it’s only a 15-minute drive to downtown Key West.

6. Waterfront Tiny House on Key Largo

You’ll love getting the chance to embrace tiny home living in this brand new Florida Keys Airbnb! You’ll be living in a private community with two beach areas, a boat ramp, a heated swimming pool, a beach volleyball court, and a gazebo for entertaining.

The inside of this modern tiny house feels surprisingly roomy. The main floor features a full-sized modern kitchen equipped with everything you need to prepare incredible meals at home. There are two bedrooms with space to sleep up to six guests, including a master suite.

This home is located right on the water with a dock for a boat. The spacious patio is the perfect place to hang out and take advantage of the BBQ grill, two large dining tables, and a special table for cleaning fish.

This home is perfect for those who love water sports as there are two kayaks and stand up paddleboards that are free for guests to use. There’s even a playground for the kids!

This home is in Key Largo, just an hours away from Miami so it’s a perfect base for exploring all the Keys has to offer! John Pennekamp Coral Reef State Park is just a 7-minute drive – you can enjoy fun water activities like a glass-bottom boat, snorkeling, sailing, and scuba tours.

Check Prices on Booking.com

Check Prices on VRBO

7. Bright Contemporary Home in Key West

Located on Key West, this contemporary 3-bedroom home is one of the best Airbnbs in the Florida Keys, especially for families or small groups. It boasts impressive ocean views, a private heated pool, and it’s within a mile of all the top sights of Key West.

The interior of this home has a luxurious and homey feel. The main space has an open-concept plan with huge windows overlooking the ocean that fill the home with natural light. The living room has modern couches, a fireplace, and a huge flatscreen TV for movie nights. It opens up to the chef’s kitchen that has everything you need to prepare a gourmet meal. If you prefer to BBQ, there’s also an outdoor grill on the patio.

You’ll have endless activities to keep you entertained during your stay. Take a stroll down to Higgs Beach Pier and Edward B Knight Pier for uninterrupted sea views. Or head over to Indigenous Park where there’s a wildlife rescue center.

And when you’re done exploring? This Airbnb’s pool is a pretty great spot to end the day. There’s plenty of space for relaxing with a covered porch, upper deck, and patio area with wicker chairs and chaise lounges.

8. Oasis in the Keys: Newly Remodeled Oceanfront Home

With stunning floor-to-ceiling ocean views in every room, a stay at this newly remodeled home is sure to be a memorable vacation with friends or family. 

This beautiful Airbnb features an open floor plan with Terrazzo floors, modern decor, and no shortage of natural light coming through the large windows. The living area has an Italian leather sectional sofa and a 55″ 4K UHD TV so it’s the perfect place to kick back and relax with a movie.

Next to the living room is the well-equipped kitchen with a full suite of stainless steel appliances, a breakfast bar, and a five-person dining table. This home has three bedrooms, each offering direct access to a patio where you can enjoy beautiful ocean views. 

The outdoor patio is a great space to unwind after a day in the sun. Fire up the gas grill and enjoy dinner outside, play a game of outdoor shuffleboard, or roast marshmallows under the stars by the outdoor fire pit.

Days here will be filled with exploration as this home comes with four kayaks, two paddleboards, and bikes to cruise around the surrounding area. This home is in Marathon, just an 8-minute drive to Cabana Club. Many other local excursions are within 2 miles including Crane Point Museums & Nature Center, Conch Air, and Island Hoppers Aerial Adventures.

Best Florida Keys Airbnbs for Large Groups and Events

9. gorgeous historic home with private pool.

This gorgeous 9-bedroom historic home is the perfect vacation rental to host a family reunion or large group event. Full of charm and character, this Airbnb has plenty of shared space for dinners and socializing, but also enough private bedrooms and bathrooms for everyone. 

Each of the bedrooms is beautifully decorated and comes with a mini-fridge and flatscreen TV. Eight of the rooms have attached verandas – perfect for enjoying your morning coffee.

Downstairs there’s a large living room and fully equipped kitchen for cooking. But the best part about this home is the outdoor area which features a gorgeous private pool, outdoor dining table, and plenty of lounge chairs for relaxing. This is the perfect space for entertaining!

The location of this Airbnb is ideal for exploring Key West. It’s located in a quiet neighborhood just three blocks away from Duval Street so you’ll be just a few minutes walk to shops, restaurants, museums, and art galleries. Even better, Simonton Beach and Fort Zachary Taylor State Park are right nearby.

Check Price & Availability on EXPEDIA

10. Colorful Key West Home on Duval Street

If you’re a large group looking to stay in the center of the action, then you’ll definitely want to check out this colorful Key West home . It occupies an enter corner of Old Town’s famous Duval Street so you’ll be steps away from the best restaurants, shops, galleries, and nightlife in Key West. But this upscale home offers plenty of privacy too.

The main floor of this home is the perfect space for entertaining large groups. The foyer opens up to the spacious living room where there’s a large sectional sofa, a 60″ flat screen SMART TV, and an iPhone docking station to play your favorite music. The first and second floors have huge porches where you can enjoy people-watching on Duval Street. 

Next to the living room is a dining area with space for 8, plus additional seating at the kitchen bar. If you need more space there’s a full dining table on the patio along with a BBQ. The fully equipped kitchen has been recently upgraded with state-of-the-art appliances and tools so you’ll be able to have fantastic group dinners here.

The best part about this home is the large private pool surrounded by a tall privacy fence. Chaise lounges and plush outdoor furniture surround the pool so there’s no shortage of space for relaxing. 

And you couldn’t ask for a better location to explore the attractions of Key West! Southernmost Point, Hemingway House, Southernmost Beach, and famous spots like Sloppy Joe’s and The Green Parrot are all within walking distance of this Airbnb.

11. Waterfront Luxury Oasis in Marathon

For the ultimate luxury escape, host your next family vacation or large group event at this stunning waterfront retreat! With 3 pools, a private beach, an outdoor spa, a Tiki Hut, and a 50-foot dock, staying at this Airbnb in the Florida Keys is like having a resort of your very own.

This villa is a dream for entertaining large groups. With 10 separate bedrooms and 9 baths, there’s room for 16 guests to stay here comfortably. Throughout the home there are several shared spaces where guests can socialize. The main floor has a spacious living room that opens up into a fully-stocked kitchen with a large dining table for enjoying group meals. There’s even a game room with a billiard table!

The best part about this luxurious vacation rental is the outdoor space. There are 3 pools with ample lounge chairs around them. Spend your days hanging out at the swim-up bar, playing pool volleyball, or sunbathing on the private beach.

This luxurious Florida Keys Airbnb is in Marathon, just one hour north of Key West. It’s an excellent location for exploring the best of what the Florida Keys has to offer. Head north to Islamorada for the best fishing in the Keys, or to Sombrero Reef and Key Largo for diving and snorkeling.

12. Real World MTV House

If you’re a fan of MTV’s Real World, then you’ll love staying in this wildly colorful party pad used to film the show’s 2006 season! With 500 feet of oceanfront property, 10 bedrooms, and incredible amenities at your disposal, staying here is like having your own personal resort.

Both the exterior and interior are painted with bright colors, which gives this home a fun and vibrant atmosphere. The main space has an open-concept floor plan with plenty of space for socializing. The living room has a large pink sectional with an indoor hot tub right next to it. It opens up into the kitchen, which is fully stocked with everything you’ll need during your stay. 

This home is a dream for hosting large groups as it has all the entertainment facilities you could ask for including your own beach, a gym, a basketball court, a tennis court, a pool table, hammocks, paddleboards, bicycles, kayaks, and more!

This Airbnb is in a quiet area in Key West where you can enjoy your privacy. And when you’re ready to hit the town it’s just 10 minutes away from Duval Street. This resort-home offers everything you need for a fun large gathering!

That’s it – 12 of the best Airbnbs in the Florida Keys! Do you have a favorite vacation rental in the Florida Keys? Let us know in the comments below.

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About the Author:

Nick took his first solo trip abroad to Ireland and Scotland when he was just 19. Since then he has visited over 70 countries around the world (plus 45 states in the USA). He coupled his passion for travel photography with Val’s passion for writing and thus Wandering Wheatleys was born. He now lives in Asheville with his two rambunctious kids, Humphrey and Wilhelminha. Besides photography, Nick loves eating the weirdest food he can find in a country (sheep’s brain currently sits in first place) and making Val get up an hour before sunrise to make sure he gets “the good light”.

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1 thought on “12 incredible airbnbs in the florida keys”.

Love the fl keys, they are beautiful, but pricey for the average Joe. Just got back from fiesta key and it’s pardise down there. Love it.

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Vacation rentals in Marathon

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Marathon

Guests agree: these stays are highly rated for location, cleanliness, and more.

Home in Key Colony Beach

Coral House: 2/2 Waterfront in KCB w/ King Beds

Dog-friendly canal-front home with waterfront patio, water views, king size beds, & a washer/dryer! Welcome to the heart of the Florida Keys. Come relax, play, and stay in Key Colony Beach. Our house is perfect for families, couples, & small groups looking to experience the Keys. Walk to nearby atttractions such as dining, live music, water sports rentals, marinas, fishing charters, private boat rentals, shopping, and more. Have a small boat or jet ski? We have a 20 foot dock that you can use.

May 13 – 20

Home in Marathon

Grouper Getaway @ Ocean Isles Fishing Village

Escape to paradise at the Grouper Getaway located at Ocean Isles Fishing Village in Marathon Key, FL. This beautifully Brand New fully furnished 1 bed/2 bath studio townhouse, offers a central location and an array of luxurious amenities for a truly unforgettable vacation. Steps away from the the Atlantic ocean, enjoy the largest pool in Marathon with clear views of the VACA Cut boat traffic and the Sombrero Light House. Enjoy fishing, paddle boarding, kayaking, tiki huts, beach, and grills.

Oct. 20 – 27

Horizon is a bright beautiful upscale home, custom designed to take full advantage of its unique ocean location. Every room, has a wide sliding glass door to oceanfront balconies. Every bedroom has a private bath. Pool with Spa, Observation Platform for those sunrises on open water, ping pong, corn toss, kayaks and paddle boards, multiple dining areas, WIFI, quality appliances, comfy cotton bedding, crib, high chair multiple TV's poolside loungers, rocking chairs & bird watching. ++++

Apr. 5 – 12

Guest suite in Marathon

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Condo in Key Colony Beach

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Florida Keys Oceanside Utopia

Create amazing memories at this beautiful oceanside home in Marathon, FL. Relax in the backyard or outdoor bar, watching boats cruise by on the aqua waters of Vaca Cut. Enjoy a fully equipped, newly remodeled and furnished duplex, beautifully decorated and ready to be your home away from home. Our waterfront location can’t be beat. Marathon has everything you need for a vacation to do it all on one Key. We can’t wait for you to experience our vacation home. Must be 25+ years old to book.

Oct. 24 – 31

Guest suite in Key Colony Beach

Turtle-By-The-Sea: the Best Deal in KCB!

A perfect get-away for couples or budget travelers, the Turtle-by-the-Sea Guest Suite is the best priced vacation rental or hotel room in the middle-keys. Together with its prime location and amenities there simply isn’t a better deal to be had! Bursting with Keys charm, this cozy retreat is the perfect place to relax & escape. Newly rebuilt & reimagined, owners Mallory & Steve infused their love of the Keys & its surrounding ocean into every aspect of their waterside home.

Sep. 17 – 24

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Sep. 14 – 21

Beach House, Private Pool & Dock, Gulf Sunset view

You don't come to the islands to stay in a town! Relax in our tropical paradise beach home away from the traffic and noise of US Hwy #1. The perfect location has now been turned into the perfect oasis. Special features include a gourmet kitchen, private pool surrounded by lush landscaping, private 300' pier/dock with a fish cleaning station. Our guests enjoy luxury bedding with quality linens, fluffy towels and bathrobes. Wireless internet service and cable tv.

Mar. 29 – Apr. 5

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Aug. 11 – 18

Apartment in Marathon

Cozy Keys Efficiency 8a

Efficiency has a queen size bed, a 3-seat leather sofa and a small dining table with 2 chairs. Private bathroom. Mini split ductless cooling AC. Kitchen is fully equipped with 4 burner stove, microwave, medium size refrigerator with freezer. Enjoy the breezes on your patio, each unit has a gas BBQ grill and a picnic bench outside. Enjoy a swim in our shared pool. Pricing include 12.5 % tax Efficiency has a 2 person maximum occupancy - no exceptions.

Oct. 18 – 25

Townhouse in Marathon

Marathon Keys Coral Lagoon Unit 2 Waterfront Villa

Welcome to paradise! We are proud to offer you one of the nicest waterfront units in Coral Lagoon! Please Note: For your safety, the entire house is sanitized prior to your arrival. Along with our standard cleaning practices we have a local company that comes in and fogs the entire house with hospital grade sanitizer.

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Marathon vacation rentals

Stay near marathon's top sights, other great vacation rentals in marathon.

Anglers Terrace, Condé Nast Traveler's Best Airbnb

Aug. 24 – 31

ABeachBungalow-60’dock w/ access to pool and beach

Apr. 26 – May 3

Camper/RV in Big Pine Key

Having fun in the lower Keys

Aug. 26 – Sep. 2

Waterfront Tropical Oasis in the FL Keys

Villa in Marathon

Sombrero Beach house with dock and tropical pool

Mar. 9 – 16

Oceanfront *PARADiSE* Amazing views, pool, dock

Captain’s Quarters Ahoy Mateys! Florida, Keys

Nov. 29 – Dec. 6

Brand New Luxury Oceanfront Home w/ Pool, 38' Slip

Jan. 20 – 27

Quick stats about vacation rentals in Marathon

Total rentals.

1.4K properties

Rentals with dedicated workspaces

610 properties have a dedicated workspace

Rentals with a pool

1.1K properties have a pool

Pet-friendly rentals

440 properties allow pets

Family-friendly rentals

1.1K properties are a good fit for families

Total number of reviews

29K reviews

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Florida Keys vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Florida Keys

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest suite in Homestead

Honeymoon Suite~Beach essentials & free parking

🌴Come and relax in our clean and cozy private guest suite, nested within a beautiful and safe gated community. Located just north of Key Largo, near Everglades National Park and Biscayne National Park. Whether you plan on exploring the fun city of Miami or enjoy the gorgeous Florida Keys, you will be in a great central location! Our guest suite has a luxurious and comfortable bed, high end amenities and a Smart TV. Everything you need to unwind, relax and recharge after a fun day of exploring! 😴

Nov 21 – 28

Tiny home in Cutler Bay

Quiet tropical Oasis setting with 1 bed and 1 bath

Tropical oasis centrally located between Miami Beach and Key Largo. Although you may never want to leave. The cozy casita with private bath and balcony is tucked away, surrounded by lush vegetation and sounds of the waterfall. Take a dip in the pool or grotto, relax with an afternoon cocktail under the tiki hut, or snooze in the hammock. During those cooler months soak in the hot tub. We have bikes available to cruise the miles of nearby paths stretching from Coconut Grove to Black Point Marina.

Oct 20 – 27

Guest suite in Marathon

Casa Mariposa: Easy walk to Sombrero Beach

Book your relaxing getaway now at Casa Mariposa in the heart of the Florida Keys! See why we were rated a top 15 cozy retreat in the Keys, 1 0f 24 amazing AirBNB rentals in the Keys, and, in 2023, 1 of 23 Amazing Airbnbs In Florida Keys. Step out from your private suite to our 50' lap pool surrounded with tropical foliage, large patio, and tropical gardens. Avoid beach parking fees with a short walk from your suite at Casa Mariposa! Contact us if you are interested in other lengths of stay.

Home in Key Largo

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Beautiful Waterfront, Modern Coastal Décor, Spacious !! Enjoy your vacation in this beautiful recently renovated home. Views from almost every window and door of the harbor. Walk to many local restaurants and bars for fresh local seafood and a cold draft beer!! Enjoy the sunsets from your private porch. Easy access to Atlantic Ocean. We Do Not Allow Fishing on our Property! 28 day I am a licensed charter captain and offer discounts to guests! Fishing, Sandbar or a Sunset Cruise!!!

Cottage in Key Largo

Charming Key Largo Cottage on the Water w/Kayaks!

Charming "Tiny House" Cottage on a main canal just two units from open water. Amazing location for boaters, fisherman and alike. This is a quaint and close knit RV park where you can keep to yourself or wander around and enjoy happy hour with new local friends. Bar none the best kayak, paddle board and fishing area. Two Tandem (each kayak accommodates two people) Kayaks and two paddle boards included in rental. Great outdoor space to dock your boat, fish off of or enjoy a few cocktails!

Oct 23 – 30

Condo in Key Colony Beach

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

Cottage in Islamorada

1 BD PRIVATE HOUSEBOAT/ COTTAGE TARPON

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! Unfortunately, we do not have spare slips for private boats at this time. A 5% lodging tax will be charged on arrival.

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

Nov 26 – Dec 3

Home in Marathon

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

Sep 14 – 21

Oceanfront Tiny Villa in the Heart of the FL Keys

Welcome to your happy place in paradise! Our oceanfront villa is located on Duck Key right outside of Marathon and next to the world famous Hawks Cay Resort. Halfway between Key Largo and Key West, it’s the perfect location to explore all our island paradise has to offer. Enjoy world class fishing, diving and snorkeling or kick back with a cold beverage and enjoy a stunning sunset on one of our covered porches. And always remember…it’s 5 o’clock somewhere!!

Sep 29 – Oct 6

Apartment in Key West

At Mine | Lovely Suite steps from Duval Street

Beautifully renovated boutique hotel suite steps from Duval Street. This property is situated on a quiet street and offers a private pool and peaceful accommodation for vacationers and business travelers. The unit features a comfortable Queen-sized bed, Mini Fridge, a microwave, Iron and iron board, hangers, TV, and AC. Indulge in Key West's warm weather year-round. This special place is close to everything, making it easy to plan your visit.

Cottage in Miami Lakes

* Lake Cottage * SpaLike Bath *

The cottage is centrally located in the serene hidden gem of Mia Lakes. Perfect for couples, solo adventurers or business travelers. You will feel hidden away from it all but yet only 5- 10 min walk from restaurants, shopping, groceries, movie theater, spa, gym etc. Our lakefront guest cottage is surrounded by lots of native plants, trees & wild life. You may swim, fish (catch & release) on the lake, as well as use of a paddle board & kayak.

Aug 23 – 30

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Florida Keys vacation rentals

Other great vacation rentals in florida keys.

Home in Key West

Romantic Retreat - 2 person K Suite, Pvt deck/Spa!

Apr 25 – May 2

Beachfront Villa - Florida Keys

Oct 14 – 21

Condo in Key West

Beach Club Ocean Front 2BR Condo

Dec 21 – 28

Villa in Duck Key

Beach House Getaway - Kayaks & 2/2.5 Villa

Nov 27 – Dec 4

Apartment in Key Largo

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Your Keys Getaway!

Mar 13 – 20

Guesthouse in Key Largo

Oceanside, 1 bedroom, Bungalow in Key Largo

Mar 18 – 25

Marathon one-level home on the Marina - with slip!

May 25 – Jun 1

Private Florida Keys vacation rentals

Cozy 1BR guestroom, private entrance, free parking

Villa in Marathon

New Aqua Lodge 2Beds 1 Bath with Full Kitchens

Apr 15 – 22

Tiny home in Key Largo

Oceanfront Lookout Point w/two Kayaks & Deck

Mar 21 – 28

The Paradise 2

Aug 17 – 24

Guest suite in Key Colony Beach

Turtle-By-The-Sea: the Best Deal in KCB!

Sep 17 – 24

Home in Key Colony Beach

Coral House: 2/2 Waterfront in KCB w/ King Beds

May 13 – 20

Beach House, Private Pool & Dock, Gulf Sunset view

Mar 29 – Apr 5

The Gulf Cottage at Marathon Key

Jul 25 – Aug 1

Florida Keys home rentals

Key Largo Waterfront Home with Tiki & Boat Dock

Sep 26 – Oct 3

Florida Keys Oceanside Utopia

Oct 24 – 31

ABeachBungalow-60’dock w/ access to pool and beach

Apr 26 – May 3

Captain’s Quarters Ahoy Mateys! Florida, Keys

Nov 29 – Dec 6

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

Nov 10 – 17

Home in Upper Sugarloaf Key

Bungalows at Sugarloaf Beach - The Lighthouse

Oct 28 – Nov 4

Grouper Getaway @ Ocean Isles Fishing Village

Waterfront Tropical Oasis in the FL Keys

Your guide to Florida Keys

All about the florida keys.

From vibrant Key West to the mysteriously named No Name Key, the Florida Keys offer historical intrigue and geographical wonder in a graceful archipelago, stretching out from the Everglades towards Havana. Postcard-worthy turquoise waters make the Keys a popular destination for sports fishing, scuba diving, and boating. If you fancy a more leisurely set of activities during your visit, boat rides in the tropical sun and snorkeling let you set your own pace for exploring the dazzling coral islands.

The strong culinary culture of the Keys is centered around fresh seafood, from mahi-mahi to snapper to blackfin tuna, alongside other edible delights, like Key lime pie on a stick. For those wanting to explore both land and sea, consider venturing into the Mel Fisher Maritime Heritage Museum or the Key West Shipwreck Treasure Museum, both of which are excellent forays into the impact the ocean has had on the history of these islands.

The best time to stay in a vacation rental in Florida Keys

The best time to look for Florida Keys vacation rentals is between March and May. There are typically fewer crowds during this time and the weather is still warm without being humid, unlike in the muggier summer months.. The islands also host a variety of events in the spring. The 7 Mile Bridge Run in April is an annual marathon spanning the entirety of one of the island’s bridges. The Taste of Key West, also in April, is an annual celebration of the various cuisines that call the archipelago home, and feature everything from fine dining to seafood shacks and food trucks. The Key West Songwriters’ Festival in May has been going strong for 25 years and features dozens of performers across genres such as country, reggae, and rock.

Top things to do in Florida Keys

Duval street.

Duval Street, running from Mallory Square to the Southernmost Point marker, is one of Key West’s most lively streets. Host to museums, shops, galleries, and cafes, Duval Street is great not only for people-watching, with its many annual parades and events, but also for learning about the history of the Florida Keys, with attractions such as the Ernest Hemingway Home and Museum, and the former Strand Theater.

Dry Tortugas National Park

Dry Tortugas National Park, 70 miles from Key West, is only accessible by boat or plane, but is a worthwhile stop on any trip to the Florida Keys. An archipelago of seven beach-ringed islands, one is taken up entirely by the preserved ruins of Fort Jefferson, which stands guard over the coral, seagrass, and shipwrecks that welcome snorkelers from around the world. Popular snorkeling spots are the Historic Coaling Pier, Fort Jefferson's moat wall, and Garden Key. Boaters can explore around Loggerhead Key's Little Africa Reef and the Windjammer Wreck.

Not to be confused with the activity, or the location of the same name in Greece, Marathon is the sportfishing center of the Florida Keys. Charters are easily arranged here for deep-sea, reef, and flats fishing. A variety of beaches and beachfront restaurants line the strip, while the former Seven Mile Bridge on the island makes a scenic path for walkers, joggers, and cyclists.

Destinations to explore

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Why was captain’s fatal boat crash settlement kept secret, but his wife’s made public?

The $16 million settlement ordered late last month in the tragic 2022 Labor Day weekend boat crash that ended the life of Our Lady of Lourdes senior Luciana Fernandez and left her classmate, soccer star Katerina Puig, needing a lifetime of medical care, is just one chapter in the ongoing legal battles surrounding prominent South Florida real estate broker George Pino — the man at the vessel’s helm.

That judgment, against Pino’s wife, Cecilia Pino, came three months after George Pino reached a confidential settlement with the Puig family for an undisclosed amount of money that will be used to fund a medical trust for Katerina.

But the April 25 order by Miami-Dade Circuit Court Judge Migna Sanchez-Llorens, which enforced a settlement reached between Cecilia Pino and Katerina’s parents Kathya and Rodolpho Puig, opened questions about why George Pino’s settlement is confidential, but his wife’s is not. And, also, why the couple was sued individually.

Cecilia Pino’s attorneys sought to keep her settlement sealed for 10 years, but the Puigs objected. Sanchez-Llorens ruled in the Puigs’ favor on April 26. Part of her argument was that the continued press coverage in the Miami Herald and other outlets was having a negative impact on State Street Realty, the company her husband operates and where she works.

Both Andrew Mescolotto, the attorney for the Pinos, and Ivan Cabrera, the Puigs’ attorney, declined to discuss the case.

Several personal injury attorneys told the Miami Herald that the way the civil case has played out is not unusual.

Ira Leesfield, a Miami attorney specializing in maritime law, explained that the parties likely agreed out of court to keep the monetary value of George Pino’s settlement confidential, but didn’t agree to do the same with Cecilia’s case.

And, if there is a disagreement, the judge is likely going to deny sealing the details of the settlement, Leesfield said.

“The judges don’t care if you want it confidential,” Leesfield said. “If one party [wants the agreement not to be confidential], they’re going to do it.”

Stuart Grossman, the head of a major South Florida personal injury law firm for decades, said the reasons for wanting to keep settlements out of the public eye vary.

“It depends on the appetite, usually of the plaintiff. Some people are very sensitive about their friends and neighbors and work colleagues open to the possibility that they are worth millions,” Grossman said. “Also, it depends on the appetite of the defendant not wanting it known he was able to pay millions of dollars out of pocket.”

“Either party can invoke this. Oftentimes it’s made a condition of one party,” Grossman said.

George Pino was behind the wheel of a 29-foot Robolo twin 300-horsepower engine center console boat on Sept. 4, 2022, returning from celebrating his daughter’s 18th birthday on Elliott Key. He was with his wife, daughter and 11 of her teenage friends — including Luciana Fernandez and Katerina Puig — heading back to the couple’s vacation home at the exclusive Ocean Reef Club gated community when he rammed into a fixed channel marker near Cutter Bank in the Intracoastal Waterway.

He was going about 50 mph, which is a high rate of speed on the water, when the vessel hit the Biscayne Bay channel marker, according to the Florida Fish and Wildlife Conservation Commission, the lead investigating agency in the case. All 14 people on board were ejected into the water. Several were injured — Katerina and Luciana critically. Luciana died the next day in the hospital. Katerina suffered blunt-force trauma to her head and is permanently disabled.

Despite more than 60 empty booze containers found on the boat when investigators hauled it out of the water, and George Pino telling an FWC officer he “had two beers,” cops almost immediately ruled out alcohol as a factor in the crash, a conclusion echoed in the final criminal complaint. Instead, the Miami-Dade State Attorney’s Office, going by the final FWC report, charged Pino with three counts of misdemeanor careless boating last August.

George Pino has pleaded not guilty, and the criminal case is pending.

Both the Puig and Fernadez families were outraged at the minor charges filed. The Fernandezes, in several statements provided to the Miami Herald since Pino was charged, pointed out that he told investigators that a contributing factor to the crash was the wake thrown by a larger boat that was coming the opposite direction in the channel moments before he hit the marker.

No one else on the Robolo, nor anyone on any of the other vessels in the area that day, saw that boat, according to the FWC’s final report.

Andres and Melissa Fernandez, Luciana’s parents, have not filed any lawsuits in the aftermath of their daughter’s death, but remain highly critical of the handling of the investigation by the FWC and State Attorney’s Office.

The family has since created a nonprofit in their daughter’s name, the Lucy Fernandez Foundation, dedicated to boating safety and providing scholarships to Our Lady of Lourdes Academy.

The Fernandezes provided the following statement to the Herald:

“The Fernandez family did not file or pursue a formal lawsuit against the Pinos because we had Katy’s best interest and her future needs in mind, not as an accommodation to the Pinos.”

The Puigs filed their lawsuit against George and Cecilia Pino in March 2023. Although George Pino was operating the boat the day of the crash and the boat’s title is only in his name, both Pinos are named separately in the lawsuit.

Specifically, George Pino was sued for negligence and negligent supervision, and Cecilia was sued for negligent supervision.

Among the list of accusations in the lawsuit is that both Pinos bought alcohol that day and allowed all of the girls on the boat to drink.

The arguments in that civil case are reiterated in yet another lawsuit that has resulted from the crash — one filed in Dade court by Hudson Excess Insurance Company in February. Hudson is the company with which George Pino had a $500,000 excess insurance policy on his boat.

The company’s lawsuit against Pino and the Puigs argues it is not obliged to pay out the $500,000 policy.

Unlike the out-of-court settlement with George Pino, his wife agreed to a consent agreement to pay the $16 million. Sanchez-Llorens then issued her judgment requiring the payment.

“It’s like going to trial, but skipping the trial,” Miami trial lawyer Judd Rosen said. “If we went to trial, the likely outcome would be $16 million.”

Rosen said he believes the Puigs and Cecilia Pino, who share the same attorney in the case, may be working together to fight back against Hudson for denying the coverage. He suggested the $16 million agreement and judgment allowed both parties to pursue a bad-faith action against the insurance company.

Rosen also said it’s typical in personal injury lawsuits to go after all involved individually, so it’s not unusual that the outcomes differed for George and Cecilia Pino.

“Technically, it’s two different cases. Two Different parties. Two different defendants,” he said.

This story was originally published May 3, 2024, 4:21 PM.

David Goodhue

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Don't expect a Miami-Key West ferry system, but these Keys commuter projects are still on

Two years after making a public ferry system connecting Miami to Key West a local priority , county officials in the Florida Keys say it might not be possible.

However, in a major update of several transportation projects for the Florida Keys this week, officials outlined that an inter-island boat system, an overhauled bus network and a new on demand car service are in the works, alongside the reconstruction of the iconic Seven Mile Bridge.

The Florida Keys Transportation Coordination Committee met on Wednesday to discuss updates to 12 projects the committee set before the Florida Department of Transportation to prioritize a couple of years ago.

One of those — a potential ferry boat making regular trips between Key West and Miami — is likely not going to happen. Rough offshore waters in the Atlantic Ocean are the biggest barrier to creating that ferry route, according to Clark.

As the population of permanent residents across the Keys rises and the island chain continues to support a huge tourist industry, transportation and traffic issues have taken center stage in local politics, alongside housing affordability.

“We realized we've almost maxed out who can live and now we've got this giant influx of folks coming in,” Clark said.

The county’s population rose by nearly 10,000 people from 2010 to 2020, according to U.S. Census data, and the Monroe County Tax Collector’s Office has reported over $80 million in tourist development tax revenue for each of the last two fiscal years.

READ MORE: The Overseas Highway is an attraction, a lifeline — and sometimes dangerous. Locals hope to make it better

Instead of a Key West-Miami ferry, Clark said, the county is in very early stages of coordinating with FDOT to apply for a federal grant that would fund a local, inter-island ferry system. The new service would aim to help alleviate traffic issues on the Overseas Highway by allowing people to island hop by boat instead of clogging up the road.

Other upcoming transportation projects

Clark also discussed progress toward bolstering Monroe County’s local commuter system. He announced that county commissioners are set to approve a vendor for on-demand electric car vehicles operating across Stock Island and Key West on May 15.

The ride servicer Freebee , which is already widely used across Islamorada, was the highest-rated bidder, according to Clark.

Pending approval from commissioners, the car service would likely begin sometime in June, Clark said. Up to 30 Ford Transit electric vans would be on-demand to pick up pedestrians from 5 a.m. to 9 p.m. 5 of the 30 vehicles would be wheelchair accessible.

“Our initial focus is workforce,” Clark said. “And the next step beyond the workforce is our local service. And then our next step beyond that is, ‘How do we reach out beyond that?’ The first is a robust, continuous commuter system that doesn't exist today.”

The county is also looking to create a local, county-wide bus system that has buses running in 30-minute intervals. Currently, Key West Transit and Miami-Dade County operate the only buses traveling across the island chain.

“Right now on a good day, we have seven to nine buses on the entire system with Key West Transit and what Miami Dade's providing for us,” Clark said. “We need 22.”

FDOT also has several upcoming projects including what will likely be the complete reconstruction of two major bridges in the Keys: Long Key Bridge and the iconic Seven Mile Bridge.

“Over the next and the current five year work plan is the Long Key Bridge, the Seven Mile Bridge — and not rehabs, [those will be] brand new bridges,” Clark said.

A public meeting to discuss the Seven Mile Bridge project is slated for May 16 .