Key West is about 130 miles from Miami, as the gull flies, and only 110 from Havana. In many ways, the compact island city feels more like a free-spirited Caribbean micronation than a part of the United States. For generations, the continental U.S.’s southernmost town has attracted the likes of Ernest Hemingway, Harry S. Truman, and Tennessee Williams, who were drawn here by its trademark brand of nautically tinged, edge-of-the-world quirkiness. These days, you can still while away lazy days in the island’s historic gardens and museums or string together a pub crawl of Duval Street’s many dive bars and saloons.
While there are plenty of hotels and resorts crowded onto the island’s roughly five square miles, there’s no better way to truly feel like a salty-dog local than to post up in a vacation rental, including a waterfront condo, a historic bungalow, or even a sailboat. As you sunbathe with a copy of The Old Man and the Sea or a Hemingway daiquiri, you just might wonder how to apply for Conch Republic citizenship.
To save you from scrolling through hundreds of listings on your own, here are seven of our favorite Airbnbs in Key West—each of which has been vetted as part of the site’s Guest Favorites program and has a score of 4.9 or higher.
This Airbnb’s backyard has a hot tub, but its front porch is also a prime spot for relaxing.
Courtesy of Airbnb/Corey Breingan
Bungalow with hot tub
- Sleeps: 6
- Book now: airbnb.com
In her description of the property, host Corey Breingan describes her two-bedroom cottage as “crawling distance” from Duval Street—and with all those rum runners flowing at area bars, it’s a detail that might come in handy. At only 300 feet from the Key West Lighthouse and 500 from the Hemingway Home and Museum, the location is one of the strong suits at this blindingly white bungalow, which features a hot tub, an outdoor shower, a private sundeck, and a front porch for people watching. Inside, the vibe is understated tropical—we’re partial to the starfish-print chairs—with plenty of wicker and a cheerful sherbet palette. Note that if you’re traveling with a larger crew, you can rent the neighboring cottage as well, increasing the total capacity to 16.
This studio-style Airbnb is ideal for couples traveling to Key West.
Courtesy of Airbnb
The Palm Suite at the Atlantis House
- Sleeps: 2
- Book now: airbnb.com
Sleep under 17-foot vaulted ceilings in this detached bungalow that makes up one half of the Atlantis House’s guest suite, both sides of which are available for rent. (The main residence is also listed on Airbnb.) The contemporary digs—with a crisp black-and-white design scheme—include useful touches like a mini Bluetooth speaker, terry cloth robes, bath salts, and a coffee pot stocked with Cuban beans. Bursting with tropical foliage, the shared backyard is a relaxing spot to unwind as you grill local pink shrimp, lounge on the chaises, or read in the shade of the gazebo, while complimentary cruiser bikes help you explore the surroundings, such as the White Street Pier one block away.
Anyone booking an extended trip to Key West will benefit from this Airbnb’s spacious kitchen.
Courtesy of Airbnb/Jenna Beldyga
Oceanfront beach club condo
- Sleeps: 5
- Book now: airbnb.com
Far from the scrum of historic Old Town, the Mid-Town neighborhood offers an oceanfront respite that’s more residential than rowdy. This two-bedroom unit in the Key West Beach Club will have you feeling like a local, thanks to condo complex amenities that include two pools, a tennis court, a fitness center, a sauna, and a shared outdoor cooking area. Inside, you’ll find yourself gravitating toward the spacious kitchen, with its large island that’s ideal for prepping fresh seafood or mixing a fruity cocktail, while the wide balcony looks out over swaying palms and a bathtub-calm stretch of the Atlantic Ocean.
Work from local artists decorate the walls of this Key West houseboat.
Courtesy of Airbnb
Off-the-grid houseboat with kayaks and paddleboards
- Sleeps: 4
- Book now: airbnb.com
There may be no better way to get in the Key West spirit than on this two-bedroom houseboat, which falls somewhere between a well-equipped floating cottage and an off-the-grid glamping retreat: That means power comes from a solar array (with a backup generator to keep things chugging along overnight), and the toilet is a marine head (you’ll get the hang of it), but there’s also a fully equipped kitchen and sleeping space for four, divided between a convertible futon and a lofted bedroom. The hosts will shuttle you out to the space, and you can request paddleboards, kayaks, or snorkel gear or book additional eco-excursions on their 26-foot boat. Out here, the move is to slow down and get comfortable: Simply enjoy the environment as you fish or swim off the back of the boat and watch for dolphins playing in the surrounding waters.
A common area at the Grand Maloney that can be used as a workspace or game area.
Courtesy of Airbnb
Mansion turned hotel that can be rented by big groups
- Sleeps: 16
- Book now: airbnb.com
In 2022, local hoteliers converted this late-19th-century mansion into the Grand Maloney Hotel, and each of its six bedrooms comes with unique details that you’d see more in an eccentric family home than a hotel: The four-person Bunk Room includes queen-over-queen oversize bunk beds, reached via a mahogany staircase; the Green Room suite is all 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. Best of all, if you’re traveling with a big group, you can rent out the entire place and lounge around the wraparound balcony, the stylish lobby, and the heated private pool out back. Check-in is contactless, so don’t expect a full-service hotel experience, but before you arrive you’ll be connected with a local guest-experience manager who can help with special requests or recommendations during your stay.
This charming two-bedroom cottage has its own plunge pool in the backyard.
Courtesy of Airbnb
Charming cottage with plunge pool
- Sleeps: 6
- Book now: airbnb.com
Located in the strollable Old Town, the Puerta Coralina cottage will charm you before you even walk through the door: The front porch sits behind a white picket fence with a bright-pink door and seafoam-green window shutters, creating a cheerful environment for relaxing with some rum or a locally brewed beer. Inside, two ceiling fans whir over the great room, where dark-wood beams and molding contrast with brightly colored design accents. (Throughout, expect subtly tropical accents like starfish lamps and seashell shower curtains.) Upstairs are two spacious bedrooms with en suite bathrooms, and one includes a private sun deck with lounge chairs. After a day out exploring the island, the best place to unwind is in the backyard, which has a plunge pool and waterfall, an outdoor shower, and a barbecue for alfresco dining.
This extra-large Airbnb has room for a group of 10 to sleep across three king beds, two twin beds, and two sleeper sofas.
Courtesy of Airbnb
Four-bedroom condo near Mallory Square
- Sleeps: 10
- Book now: airbnb.com
Great for groups, this four-bedroom penthouse condo forgoes beachy clichés for an understated urbane elegance. It looks more like a big-city loft apartment than somewhere you’d expect in the Keys. There’s an open floor plan with 12-foot ceilings, plenty of exposed brick, wooden-bead chandeliers, and a statement blue kitchen island with counter seating for four. If you miss that famous Keys kitsch, you’re in luck: The newly renovated building is just steps from Mallory Square, which has a nightly “sunset celebration” that has been going strong since the 1960s and includes live music and performers like sword swallowers, unicyclists, jugglers, and magicians, not to mention cats jumping through fiery hoops.
This story was originally published in 2023; it was most recently updated with new information on May 24, 2024.
