15 Best Airbnbs in Key West, FL (2022 Edition)


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Florida, the Sunshine State, is a popular destination for snowbirds escaping the cold and those hunting for a sunny beach destination. On the very tip of Florida lies Key West, a stunning beach town known for its unique conch-style houses and Caribbean-like atmosphere. It is also home to the world’s third largest barrier coral reef, making it the ideal destination for divers and snorkel enthusiasts. 

When planning a trip to the southernmost point in the United States, you’ll want to make sure you’re arriving at one of the best Key West Airbnbs. We want that for you, too, and have handpicked a list of the best Airbnbs in Key West so that you can spend more time packing and less time planning. To ensure you are getting the crème de la crème, all of the Airbnbs listed are hosted by Airbnb superhosts – rental owners with a history of providing outstanding hospitality to their guests.

Related: 15 Best Airbnbs in Florida, USA

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Duval Street Retreat for Larger Groups

This funky seaside-themed house is perfect for those traveling in a group of 12 or fewer. 

This rental is made up of four cottages connected by a shared courtyard, making it ideal for those who still want some privacy while on vacation with their family and friends. 

In the first cottage, there is a king-size bed, a sofa bed, a full kitchen, a TV, and a private balcony. The second cottage has a studio-style layout with a king-size bed, a TV, and a small kitchenette. The third cottage has an ocean theme with a queen-size bed and kitchenette. The fourth cottage is decorated with a nautical theme and has two queen-size beds as well as a kitchenette. Each cottage has a bathroom with a walk-in shower. 

The center courtyard has a beautiful 20-foot beach mosaic and includes a large outdoor dining set and a barbecue. There is also an area to hang your diving and snorkel gear after a day on the water. 

This Key West Airbnb is located in the historic area of Duval, putting guests within walking distance of the Southernmost Point of the Continental US and the Hemingway Home and Museum.

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Colorful Condo for Two 

This bright and vibrant condo is perfect for couples or solo travelers looking to be close to Duval. 

The rental is located in Old Town, just steps away from popular restaurants and bars. There is free street parking, but for those looking for an alternative way to get around, the Old Town Trolley and Conch Tour Train have stops nearby. 

Inside, the home has a classic Caribbean feel with an array of colorful walls and beach-themed décor. The full kitchen has all the cooking essentials, and guests can enjoy their meals at the breakfast bar. In the bedroom, there is a comfortable king-size bed, a Smart TV, and a desk and chair, perfect for working remotely or getting ready for a night out. There is also a sound machine beside the bed for those who need help falling asleep. 

After a day at the beach, guests can relax on the leather sofa in the living room and stream their favorite shows and movies on the Smart TV. The bathroom features a spacious glass walk-in shower. 

Perhaps the best part of this rental is the wrap-around porch, where guests can enjoy a glass of wine at sunset in the Adirondack chairs. 

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Chic Duplex With Parking and Pool 

If you are looking for a stylish vacation rental in Key West that has hotel-like amenities with all the comforts of home, this is for you. 

This two-bedroom duplex is decorated with a light West Indies motif and comfortable furnishings, making for a relaxed and chic space. In the living room, guests can unwind on the blue velvet furniture and make a coffee from the Keurig. The rental does not have a kitchen, but there is a minifridge, microwave, and complimentary continental breakfast provided each day. 

There are two bedrooms upstairs, each with two queen-size beds. In the hallway, there is a small living area with a couch where guests can relax with a good book. The bathroom features gorgeous Mexican tiles and a shower. After a day of touring the town, guests can unwind with a cocktail on the spacious second-floor balcony, and people-watch on the streets below. 

This Airbnb in Key West comes with access to a shared community pool, a courtyard with sun loungers, gardens, and a gazebo. Guests also have access to the private parking lot beside the building as well as street parking, and Duval Street is only half a block away. 

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Historic Studio Apartment Near Duval Street

This bright and airy studio apartment is perfect for families or couples looking for a quiet retreat in the Keys. 

Inside, the home has fresh white walls with wood accents and exposed brick. In the bedroom area, there is a comfortable king-size bed with a TV in front of it. The living area has a pullout couch, making this rental suitable for up to four guests. Guests can store their luggage in the front entryway’s closet. Perhaps the best part of this rental is the fully equipped kitchen featuring stainless-steel appliances, a toaster, a blender, and everything else needed to prepare a meal. 

The bathroom is quite spacious and includes a washer and dryer for those looking to do some laundry while on holiday. After a day at the beach, guests can enjoy a relaxing rinse in the modern walk-in shower. 

There are plenty of paid parking lots close to this Key West Airbnb. Mallory Square, the Key West Aquarium, and Key West Seaport are all less than a 10-minute walk away. The home is tucked away from the street, offering maximum privacy. 

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Floating Tiki Suite

Are you looking for a unique Airbnb in Key West? Well, it doesn’t get more unique than a floating tiki house! 

This adorable floating suite with a thatched roof offers a one-of-a-kind experience of glamping right on the ocean. Three sets of French doors open onto the water where guests can swim, paddleboard, or snorkel right from the rental. Guests can also enjoy picturesque Florida sunsets from the porch’s hammock hanging over the water or with a glass of wine on the lounge chairs. 

Inside, the suite features gorgeous Brazilian hardwood floors and a plush king-size bed. The home’s lights are completely voice-controlled through an Alexa, so guests need only ask her to play music or turn off the lights. In the bathroom, there is a shower and an electric macerating toilet. Since the house is made of wood, there are no cooking appliances other than a Keurig on board, and smoking is not permitted. 

As this Key West Airbnb is located on the water, guests will need to hire a water shuttle to get to the rental. Since the rental is classified as a boat, renters will need to have a boater’s license in order to stay on board or be born after 1987, as required by Florida law. 

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Cozy Cottage With a Private Hot Tub

If you are in search of a short-term rental in Key West that offers a romantic setting and is accessible for those with mobility issues, this pet-friendly Airbnb is for you. 

The cottage was built in the 1800s as a cigar maker’s cistern and has been beautifully renovated with a delightful Caribbean motif. Inside, guests can listen to music on the Bose Bluetooth speaker or simply ask Alexa to play their favorite bands. There are no steps outside or in the home, making this ideal for those with accessibility needs. 

The bedroom features a king-size bed where guests can relax and access their favorite streaming channels on the wall-mounted Smart TV. In the bathroom, the space is decorated with Tommy Bahama amenities, and there is a tub and shower with an accessibility rail. The kitchenette is well stocked with essentials like a minifridge, toaster, coffee maker, electric skillet, and more. 

Outside, guests have a private backyard complete with a hot tub and table and chairs. The front of the cottage opens to the shared pool area where there is a private outdoor shower, a barbecue, and a gazebo with games like dominoes, cornhole, and Cards Against Humanity. 

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Three-Bedroom House Near Truman Little White House

This three-bedroom house for rent in Key West is the perfect retreat for your family and furry friends.

The home is decorated in a modern Mediterranean style with beautiful wooden furnishings and high ceilings. In the full kitchen, there is plenty of counter space for cooking as well as stainless-steel appliances. The living room features a sectional sofa surrounded by French glass doors leading outside, creating a bright and peaceful space. 

The master bedroom features a luxurious king-size bed, a private balcony, and an en suite bathroom with a walk-in shower. In the second upstairs bedroom, there is a queen-size bed, a TV, and an en suite bathroom with a spacious walk-in rain shower. The third bedroom is located downstairs and has a queen-size bed. 

Outside, there is a large patio where guests can grill a meal on the barbecue or lie back and tan on the sun loungers. Guests can also use the Bose speaker and jam out while enjoying a drink. The entire backyard is surrounded by shrubbery and palm trees, optimizing privacy. A covered carport for one car can be found out front, and guests can find additional paid parking nearby. 

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Condo Near Fort Zachary Taylor Historic State Park Beach

If you are looking for a beach house rental in Key West, then consider this tropical one-bedroom condo that is within walking distance of Fort Zachary Taylor Historic State Park Beach!

The home features stylish contemporary furnishings and is painted with vibrant Caribbean colors, creating a relaxing tropical feel. Guests can soak up the Florida sun rays on the deck’s sun loungers or enjoy their morning coffee on the outdoor bistro set. The condo is located in a gated community with access to a shared pool. 

In the living room, guests can watch TV or read a book surrounded by nautical-themed décor. The full kitchen has a unique porthole window and comes well stocked with all the essentials for preparing a meal. In the bedroom, there is a queen-size bed and curtains with waterfall fairy lights that give the space a soft and warm feel. The bathroom features travertine tile and a shower and tub. Guests can pack light for their holiday here as the rental also includes a washer and dryer. 

There is one parking space available for guests in a residential parking garage. If you are looking for an extended holiday, superhost Wendy allows for long stays. 

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Historic Condo With Parking

This vacation home for rent in Key West is perfect for families or a group of friends of four or fewer looking to stay in Old Town. 

Inside, the home has been decorated with a mixture of vintage and contemporary furnishings. The full kitchen has an expandable dining table that can seat four. Guests can enjoy a cup of coffee from the Keurig on the porch’s comfortable couch and lounge chair. A washer and dryer can also be found inside. 

Superhost Ruth has stocked the bathroom with all the essentials, such as shampoo, conditioner, a blow dryer, and extra beach towels. In the bedroom, there is a king-size memory foam bed, a TV, and an iHome speaker alarm clock. There is a pullout couch in the living area, making this rental suitable for four guests or fewer. 

This Key West Airbnb comes with access to a shared pool in a hotel located opposite the entryway. Free on-site parking is also included. There are plenty of restaurants and bars on the doorstep of this rental, and Mallory Square and the Key West Shipwreck Museum are roughly a 15-minute walk away. 

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Tropical All-Inclusive Suite 

Can’t decide between a hotel or a rental? There’s no need to compromise because this Airbnb in Key West has the best of both worlds.

Guests here have an all-inclusive setup with complimentary breakfast, brunch, lunch, and happy hour every day. Getting around town is hassle-free here as there is free on-site parking and complimentary bikes to use. The room is one of six rentals available at Andrews Inn. The property’s amenities include a shared pool, a Tiki bar, and a communal library. 

Inside the suite, guests can unwind on a comfortable king-size bed fitted with tropical-themed bedding. The living area includes a pullout couch, a wall-mounted TV, and an icebox with glasses. There is a closet in the corner of the room that is perfect for luggage storage. In the bathroom, there is a large well-lit vanity and a shower. After a day at the beach, guests can enjoy an evening cocktail or play a card game on the private patio’s dining set. 

This Airbnb in Key West is located steps from the Hemingway House and Museum and the Key West Lighthouse. The popular restaurants and bars on Duval Street are also within walking distance. 

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Three-Bedroom Townhouse on Stock Island

If you want to rent a house in Key West that can sleep up to eight guests, this family-friendly townhouse is for you. 

This three-bedroom home is located 10 minutes from downtown Key West across from the Key West Golf Club on Stock Island. The house is in the gated community of Coral Hammock and boasts a luxurious shared saltwater pool and a gym. Just a short walk from the rental, guests will find plenty of restaurants, bars, and shops. 

The home’s interior features vibrant walls and classic beach décor, creating a bright and fun space. In the full kitchen, there are stainless-steel appliances and plenty of counter space for cooking. The dining room has a large table big enough for the whole family to enjoy a meal together. 

The master bedroom upstairs features a king-size bed, a TV, and a set of French doors that open to a private patio. After a long day of touring the town, guests can enjoy a relaxing soak in the master bedroom’s large tub. The second bedroom has two sets of wooden bunk beds and an en suite bathroom with a shower and tub. The third bedroom has a queen-size bed, TV, and walkout to the lower patio. 

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Luxurious House With Private Jacuzzi Pool 

One look at this luxurious Airbnb, and you’ll quickly see why it made our list of the best Airbnbs in Key West. 

This pet-friendly home sports many modern and extravagant details, from a state-of-the-art chef’s kitchen to a 12-person hardwood dining table. In the living room, guests can choose a book from the extensive library or relax and watch the news with their morning coffee. 

The master bedroom is connected to the courtyard and features a living room set, a luxury king-size bed, a kitchenette, and a TV. In the second bedroom, there is a king-size bed, and in the third and fourth bedrooms, there are queen-size beds. The fifth bedroom is a separate studio with a full kitchen, a queen-size bed, a living room, and a bathroom with a claw-foot bathtub. This rental can sleep 12 guests.

Outside, guests can soak up the Florida sun rays on the sun loungers beside the heated saltwater pool complete with Jacuzzi jets. The backyard also has a covered patio set and another patio set on the faux grass. Guests will also have access to bikes on the property. 

This Key West Airbnb is located in the heart of the Cuban district, steps away from coffee shops and restaurants. 

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The Conch House

From the second you step into the front foyer of this lavish Airbnb in Key West, you’ll be transported into a tropical wonderland of bright colors and classic Key West décor. 

This five-bedroom rental is the perfect rental for those wishing to experience a classic Florida home with plenty of room for the whole family. Outside, guests can spend their days floating in the pool and their nights soaking in the gorgeous heated spa, which includes a waterfall feature. There is a separate outdoor fridge for storing beers, as well as a barbecue and a covered dining area.

A set of French doors opens to the living room, where guests can unwind and watch TV. In the full kitchen, there is a seven-person dining table and plenty of space for cooking for larger groups.

There are two large bedrooms on the second floor, each with a king-size bed and a door to the second-floor patio. The third floor also has two bedrooms – one with a queen-size bed and a second with two queen-size beds. In a separate building beside the pool is the fifth bedroom; it has a king-size bed and an en suite bathroom. 

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Two-Bedroom Resort Condo on Smathers Beach

If you are looking to stay close to the beach, this is one of the best Airbnb rentals in Key West for you. 

The rental includes access to a shared full-size Olympic swimming pool, three tennis courts, and a 20-person hot tub. In the evening, guests can take a leisurely sunset stroll on Smathers Beach located across the street or walk to one of the many restaurants nearby. 

Inside, the home has been decorated with comfortable furnishings and a classic beach-themed motif. In the master bedroom, there is a king-size bed, a TV, and a vanity desk with a makeup mirror where guests can get ready for a night on the town. The master bedroom’s en suite bathroom is quite spacious and boasts a double vanity, an air jet tub, and a large walk-in rain shower. In the second bedroom, there is a twin bed and a queen-size bed. Both bedrooms have access to the balcony. 

The full kitchen includes a wet bar, a breakfast table, and a six-person dining table. Guests can watch a movie on the flatscreen TV or relax with a book on the pullout couch in the living room.

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Modern House With a Pool Near Duval Street

This luxurious three-bedroom Airbnb in Key West is a hidden gem located right in the hustle and bustle of the Historic District. 

Guests can spend their days swimming in the private pool or tanning on the sun loungers with a cocktail in hand. The backyard also features a dining set, a private outdoor shower, and hanging fairy lights. On the second patio off of the kitchen, guests will find a four-person dining set and a barbecue surrounded by lush tropical plants. 

Inside, the home has been decorated in a calming neutral palette coupled with comfortable contemporary furnishings that create a truly relaxing space. In the living room, there are plenty of seating spaces where guests can relax with a book or watch TV. The full gourmet kitchen includes both a Keurig and a 12-cup coffee maker for caffeine enthusiasts.

In the master bedroom, there is a king-size bed, a TV, and an en suite bathroom with a claw-foot bathtub and walk-in shower. The second bedroom is located on the main floor and has two single beds. On the third floor, another bedroom features a couch, a king-size bed, and a TV. This rental can sleep eight guests using the pullout couch in the living room. 

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A trip to Key West Florida is sure to be unforgettable. With its turquoise waters and lively downtown neighborhoods, you’ll probably never want to leave, especially if you’re staying in one of these Airbnbs.

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