Airbnb Florida Keys: Apartments, Condos, Cottages, Tiny Houses, Houseboats, Historic Homes, & Villas

12 Incredible Airbnbs in the Florida Keys

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!

Top 10 Things To Do in the Florida Keys

Florida Keys Airbnb: Apartments, Condos, Cottages, Tiny Homes, Houseboats, Historic Homes, & Villas
  1. Walk Duval Street and explore the many museums, souvenir shops, galleries, and cafés. This is a great place for nightlife and people-watching!
  2. 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.
  3. Go fishing in Marathon, the commercial and sportfishing center of the Middle Keys.
  4. Visit Crocodile Lake National Wildlife Refuge, which protects the last remnants of the American crocodile’s natural habitat.
  5. 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.
  6. Visit Fort Zachary Taylor Historic State Park to learn about the history of Fort Taylor and its part in the Civil War. 
  7. 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.
  8. 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!
  9. 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.
  10. Head to the southernmost tip of the continental USA and take an insta-worthy picture with the monument.
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Why Stay in an Airbnb in the Florida Keys

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. 

Search Florida Keys Hotels and Vacation Rentals

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

Coolest Airbnbs in Florida Keys: Floating House
Images courtesy of Airbnb

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

Best Florida Keys Airbnbs & Vacation Rentals: Dock Studio Apartment
Images courtesy of Airbnb

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. 

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

Florida Keys Airbnbs & Vacation Homes: Key West Sailboat
Images courtesy of Airbnb

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

Best Airbnbs in Florida Keys: Key West Houseboat
Images courtesy of Airbnb

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.

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6. Waterfront Tiny House on Key Largo

Best Florida Keys Airbnbs & Vacation Rentals: Dockside Tiny House
Images courtesy of Tiny House on the Water

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.

7. Bright Contemporary Home in Key West

Best Airbnbs in Florida Keys: Bright, Central House
Images courtesy of Airbnb

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

Best Florida Keys Airbnbs & Vacation Rentals: Oceanfront House
Images courtesy of Airbnb

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.

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9. Gorgeous Historic Home with Private Pool

Florida Keys Airbnbs & Vacation Homes: Historic House
Images courtesy of Gorgeous Historic Home

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

Airbnbs in Florida Keys Vacation Homes: Colorful House
Images courtesy of Southernmost Hospitality VII

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.

Check Price & Availability on VRBO

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11. Waterfront Luxury Oasis in Marathon

Best Airbnbs in Florida Keys: Waterfront Villa
Images courtesy of Airbnb

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

Unique Florida Keys Airbnbs & Vacation Rentals: Real World House
Images courtesy of 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!

Check Price & Availability on VRBO

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 Wheatley

    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”.

1 thought on “12 Incredible Airbnbs in the Florida Keys”

  1. 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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