7 Airbnbs in Key West Perfect for a Coastal Escape

Key West lies about 130 miles from Miami and just 110 miles from Havana. This compact island city often feels more like an independent Caribbean paradise than part of the U.S. Over the years, this southernmost town has drawn icons like Ernest Hemingway, Harry S. Truman, and Tennessee Williams, all captivated by its quirky, nautical charm. Today, you can still spend leisurely days exploring the island’s historic gardens and museums or enjoy a lively pub crawl through Duval Street’s many dive bars and saloons.

While the island's five square miles host plenty of hotels and resorts, nothing compares to the experience of staying in a vacation rental—be it a waterfront condo, a vintage bungalow, or even a sailboat. As you bask in the sun with a copy of The Old Man and the Sea or sip a Hemingway daiquiri, you might find yourself pondering how to become a citizen of the Conch Republic.

To spare you the hassle of sifting through countless listings, we’ve compiled seven of our top Airbnbs in Key West—each carefully selected as part of the site’s Guest Favorites program, boasting a rating of 4.9 or above.

Bungalow with a hot tub

Host Corey Breingan describes her two-bedroom cottage as being just a “crawling distance” from Duval Street, which could be helpful with all the rum runners at local bars. Located only 300 feet from the Key West Lighthouse and 500 from the Hemingway Home and Museum, this strikingly white bungalow offers a hot tub, an outdoor shower, a private sundeck, and a front porch perfect for people-watching. Inside, it boasts an understated tropical vibe—we love the starfish-print chairs—complete with wicker furnishings and a bright sherbet color scheme. If you're traveling with a larger group, you can also rent the neighboring cottage, accommodating up to 16 guests in total.

The Palm Suite at Atlantis House

Experience sleeping beneath 17-foot vaulted ceilings in this charming bungalow, which comprises one half of the guest suite at the Atlantis House—both halves are available for rent. (The main residence is also listed on Airbnb.) This modern space, featuring a sleek black-and-white design, includes amenities like a mini Bluetooth speaker, terry cloth robes, bath salts, and a coffee maker stocked with Cuban beans. Surrounded by lush tropical greenery, the shared backyard is a tranquil oasis for grilling local pink shrimp, lounging on chaises, or enjoying a book in the gazebo's shade. Complimentary cruiser bikes make it easy to explore nearby attractions, such as the White Street Pier just a block away.

Condo at the oceanfront beach club

Situated away from the hustle of historic Old Town, the Mid-Town neighborhood provides a more residential and serene oceanfront experience. This two-bedroom unit at the Key West Beach Club will make you feel like a local, thanks to amenities that include two pools, a tennis court, a fitness center, a sauna, and a communal outdoor cooking space. Inside, you'll be drawn to the spacious kitchen with its generous island, perfect for preparing fresh seafood or mixing fruity cocktails, while the expansive balcony offers views of swaying palms and the tranquil Atlantic Ocean.

Off-the-grid houseboat featuring kayaks and paddleboards

Experience the true spirit of Key West on this two-bedroom houseboat, which blends the comforts of a floating cottage with the adventure of off-the-grid glamping. Power is provided by solar panels, with a backup generator for overnight needs, and the toilet is a marine head (you’ll quickly adjust). Enjoy a fully equipped kitchen and accommodations for four, including a convertible futon and a lofted bedroom. The hosts offer shuttle service to the boat, and you can request paddleboards, kayaks, snorkel gear, or book eco-excursions on their 26-foot vessel. Here, the key is to unwind and enjoy nature—fish, swim from the boat, and watch dolphins frolicking in the waters around you.

Hotel mansion available for large group rentals

In 2022, local hoteliers transformed this late-19th-century mansion into the Grand Maloney Hotel. Each of its six bedrooms boasts distinctive features reminiscent of a quirky family home rather than a typical hotel: The Bunk Room accommodates four with its queen-over-queen oversized bunk beds, accessed via a mahogany staircase; the Green Room suite showcases exposed brick and tropical botanical wallpaper; and the Carriage House is a detached cottage with ceiling beams, coral rock floors, and a patio shaded by native poinciana trees. For larger groups, the entire property can be rented, allowing you to relax on the wraparound balcony, in the stylish lobby, or by the heated private pool out back. Check-in is contactless, providing a more independent experience, but you'll be in touch with a local guest-experience manager before your arrival for any special requests or recommendations during your stay.

Lovely cottage with a plunge pool

Nestled in walkable Old Town, the Puerta Coralina cottage will captivate you before you even enter. The front porch, framed by a white picket fence, showcases a bright pink door and seafoam green window shutters, creating a joyful atmosphere perfect for enjoying a rum or a local beer. Inside, two ceiling fans spin gently over the great room, where dark wooden beams and moldings contrast with vibrant design accents. Expect charming tropical touches like starfish lamps and seashell shower curtains throughout. Upstairs, you'll find two spacious bedrooms with en suite bathrooms; one includes a private sun deck with lounge chairs. After a day of exploring the island, relax in the backyard, which features a plunge pool with a waterfall, an outdoor shower, and a barbecue for delightful alfresco meals.

Four-bedroom condo close to Mallory Square

Ideal for groups, this four-bedroom penthouse condo opts for a refined urban style over typical beach aesthetics. It resembles a spacious loft apartment more than a typical Keys accommodation. Featuring an open floor plan with 12-foot ceilings, abundant exposed brick, wooden-bead chandeliers, and a striking blue kitchen island with seating for four, it exudes sophistication. If you're yearning for that quintessential Keys charm, you'll be pleased to know that this newly renovated building is just a short walk from Mallory Square, famous for its nightly “sunset celebration” that has delighted visitors since the 1960s, featuring live music, sword swallowers, unicyclists, jugglers, magicians, and even cats leaping through flaming hoops.

This article was originally published in 2023 and was last updated with new information on May 24, 2024.