Whether you’re looking to stroll the historic streets of Old Town, swim on island beaches, or hop on a sunset cruise, you can do it all and more in Key West. Florida’s most free-wheeling town is an absolute joy to visit all year round—where everything revolves around catching the sunset, sipping something frosty, and spending plenty of time out on the water.
While the Keys are home to some spectacular hotels and resorts, to really make sure you get beyond the main tourist drag and party zone of Duval Street (and get a taste of what it’s like to be a local), consider booking a rental. Whether you’re looking to stay within walking distance from the town’s most legendary bars, or prefer something more secreted away (perhaps with a private pool for cooling off), fun-loving Key West and its fellow Florida Keys are like no place else in the country.
Below, we’ve rounded up 13 of the most atmospheric Key West Airbnbs and vacation rentals on the island for your next trip—no matter if you’re exploring the island on your own, looking for a romantic hideaway, or bringing along your extended family, there’s a gorgeous Key West home just waiting to host you.
While we have not stayed in every Airbnb featured, unless otherwise stated, these listings are vetted based on Superhost status, amenities, location, previous guest reviews, and decor.
