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 and 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.
Beautiful three-bedroom sailing yacht
Sleeps: 6Highlights: Fishing and snorkeling gear, Yeti cooler, outdoor shower Book now: From $289 per night, airbnb.com
Get in the seafaring spirit of the Keys on the 43-foot masthead sloop yacht Sailing Vessel Maruquis, which is owned by a high school science teacher turned sailing captain. The surprisingly spacious interiors include three staterooms, a full galley, a salon, and two heads—and if you have no clue what any of those rooms mean, be sure to learn some basic sailing lingo before getting on board! The boat also comes equipped with a swim ladder, life jackets, and snorkeling gear in case you want to get up close and personal with the dolphins, manatees, and sea turtles that frequent these waters. Keep in mind this vessel is anchored just offshore from Key West (not docked), so guests will need to arrange water taxi service via Ship2Shore shuttle services for an additional fee.
Private villa steps from Duval Street
Sleeps: 4Highlights: Bluetooth sound system, shared pool, barbecue grillBook now: From $789 per night, airbnb.com
You have no choice but to slow down to island time as you approach Villa Serendipity: After entering through a bamboo-lined tropical garden and past a gurgling fountain, you’re greeted at the front door by a statue of a tropical-drink-swigging parrot in a Hawaiian shirt and a bucket hat. The interiors are brimming with similarly beachy touches, like coral-print bedding, mosaics of crashing waves, and a seafoam-green mini fridge in the main bedroom. The rental is particularly well-stocked for new parents, thanks to a crib and a pack and play. Also useful are the complimentary beach bag, towels, umbrellas, and snorkeling gear, which means you can leave several bulky items from home off your packing list.
Hot tub home for six
Sleeps: 6Highlights: Hot tub, washer and dryer, outdoor shower Book now: From $983 per night, 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.
The Palm Suite at the Atlantis House
Sleeps: 2Highlights: Cruiser bikes, backyard with grill, Bluetooth speaker Book now: From $464 per night, 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 was also just listed on Airbnb.) The contemporary digs—with a crisp black-and-white design scheme—include useful touches like a mini Bluetooth speaker, cotton robes and 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.
Downtown Duval Street condo
Sleeps: 4Highlights: Private balcony, free beach gear, washer and dryerBook now: From $628 per night, airbnb.com
Homey and well-appointed, this cozy two-bedroom condo unit feels miles from the hive of activity on Duval Street, even though the nightlife corridor is just half a block away via an alley. The decor skews sophisticated with only the subtlest nods to the beachy surroundings, including a tabletop tic-tac-toe board that swaps out the Xs and Os for starfish and sand dollars. Digital nomads will dig the smart computer desk setup and the Keurig coffee machine; vacationers will appreciate the bookshelf stocked with board games and beach reads (think Danielle Steel and John Grisham). Bonus points for the ecofriendly Puracy toiletries.
Three-bedroom Duval Street penthouse
Sleeps: 8Highlights: Heated pool, hammock, expansive kitchenBook now: From $788 per night, airbnb.com
Sprawling over 2,200 square feet of living space and an additional 2,000 square feet of porches and decks, this elegant two-floor property occupies prime real estate on Duval Street, with a balcony overlooking the ornate facade of the 1890 San Carlos Institute, a Cuban heritage center and museum across the way. Warm woods, rattans, and neutral-toned fabrics combine to create a breezy island atmosphere, with plenty of ceiling fans and nooks for quiet contemplation, from a hammock on the rooftop sundeck to a palm-lined plunge pool with a spa-like waterfall. Ideal for large groups, the space includes an outdoor dining table that seats eight, a crib, and a washer and dryer.
Oceanfront beach club condo
Sleeps: 4Highlights: Two pools, tennis court, fitness centerBook now: From $828 per night, 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.
At the time of publishing, these Airbnbs all have an overall rating of 4.90 or higher and all positive reviews from previous guests.
Nicholas DeRenzo Nicholas DeRenzo is a freelance travel and culture writer based in Brooklyn. A graduate of NYU’s Cultural Reporting and Criticism program, he worked as an editor at Arthur Frommer’s Budget Travel and, most recently, as executive editor at Hemispheres, the in-flight magazine of United Airlines. His writing has appeared in the New York Times, New York, Travel + Leisure, Condé Nast Traveler, Sunset, Wine Enthusiast, and more.