Key West is about 130 seagull miles from Miami and only 110 from Havana. In many ways, the compact island city feels more like a free-spirited Caribbean micronation than part of the United States. For generations, the southernmost city in the continental United States has attracted the likes of Ernest Hemingway, Harry S. Truman and Tennessee Williams, who were drawn here by its trademark nautical, end-of-the-world-tinged quirkiness. . These days you can still have lazy days in the island historical gardens and museums or take a pub crawl through the many pubs of Duval Street bars and dive lounges.
While there are many hotels and resorts crowded across the roughly five square miles of the island, there’s no better way to truly feel like a salt-dog local than to post in a vacation rental, including a waterfront condo , a historic bungalow or even a sailboat. While sunbathing with a copy of The old Man and the Sea and a Hemingway daiquiri, you might be wondering how to apply for Conch Republic citizenship.
To save you from sifting through hundreds of listings on your own, here are seven of our favorite Airbnbs in Key West.
Inside the 43ft masthead sloop yacht Sailboat Maruquiswhich can be booked on Airbnb.
Courtesy of Airbnb/Daniel Wallace
Beautiful three bedroom sailboat
- Sleeping: 6
- Strong points: Fishing and snorkeling equipment, Yeti cooler, outdoor shower
- Book now: From $289 per night, airbnb.com
Step into the seafaring spirit of the Keys on the 43-foot masthead sloop Sailboat Maruquis, which is owned by a high school science teacher turned sailing captain. Surprisingly spacious interiors include three cabins, a full galley, saloon and two bathrooms. If you have no idea what these pieces mean, be sure to learn some basic sailing lingo before you get on board! The boat is also equipped with a swim ladder, life jackets, and snorkel gear in case you want to get up close with the dolphins, manatees, and sea turtles that frequent these waters. Keep in mind that this ship is anchored just off Key West (not docked) so you will need to arrange a water taxi service via Vessel2Shore shuttle services at an additional cost.
There’s no mistaking where you woke up with beachy touches like coral print bedding and navy blue walls.
Courtesy of Airbnb/Cindy Verne
Private villa steps from Duval Street
- Sleeping: 4
- Strong points: Bluetooth audio system, shared swimming pool, barbecue
- Book now: From $789 per night, airbnb.com
You have no choice but to slow down on island time as you approach Villa Serendipity: After entering a tropical garden lined with bamboo and past a gurgling fountain, you are greeted at the front door by a statue of a tropical-drink-swigging parrot in a Hawaiian shirt and bucket hat. Interiors are full of similar beach touches, like coral-print bedding, crashing wave mosaics, and a sea-foam green mini-fridge in the master bedroom. The rental is particularly well provided for new parents, thanks to a cradle and a pack and play. Beach bag, towels, umbrellas and snorkeling gear also come in handy, meaning you can leave several large household items out of your packing list.
This Airbnb’s backyard has a hot tub, but its porch is also a great place to hang out.
Courtesy of Airbnb/Corey Breingan
Home spa for six
- Sleeping: 6
- Strong points: Spa, washer and dryer, outdoor shower
- Book now: From $983 per night, airbnb.com
In his description of the property, host Corey Breingan describes his two-bedroom cottage as “creeping distance” from Duval Street – and with all those rum runners pouring into the bars in the area, that’s a detail that could be useful. Just 300 feet from the Key West Lighthouse and 500 from the Hemingway House and Museum, location is one of the highlights of this blindingly white bungalow, which features a hot tub, an outdoor shower, a private deck and a porch for people watching. Inside, the vibe is understated tropical — we love the starfish-print chairs — with lots of wicker and a cheery sherbet palette. Note that if you are traveling with a larger crew, you can hire the neighboring cottage thus, increasing the total capacity to 16.
If you book all three Airbnbs at Atlantis House, you have room to sleep up to 10 people.
Courtesy of Airbnb/Shari Ocampo
The Palm Suite at Atlantis House
- Sleeping: 2
- Strong points: Cruiser bikes, garden with grill, Bluetooth speaker
- Book now: From $464 per night, airbnb.com
Sleep under 17-foot vaulted ceilings in this free-standing bungalow that makes up half of Atlantis House’s guest suite, both sides of which are available for hire. (The Principal residence (Also listed on Airbnb.) Contemporary digs — with a crisp black-and-white design scheme — include helpful touches like a mini Bluetooth speaker, cotton bathrobes and bath salts, and a coffeemaker stocked with Cuban beans. Brimming with tropical foliage, the communal backyard is a relaxing place to unwind while you grill local prawns, lounge on the chairs, or read in the shade of the gazebo, while complimentary cruiser bikes take you help explore the surrounding area, such as the White Street Pier a block away.
A cozy living room leads to a private balcony in this condo near Duval Street.
Courtesy of Airbnb/Maja Williams
Duval Street Downtown Condo
- Sleeping: 4
- Strong points: Private balcony, free beach equipment, washer and dryer
- Book now: From $628 per night, airbnb.com
Inviting and well-appointed, this cozy two-bedroom condo feels miles away from the hive of activity on Duval Street, even though the nightlife corridor is just half a block away via an alley. Decor is sophisticated with only the most subtle nods to the beach surroundings, including a tabletop tic-tac-toe board that replaces Xs and Os with starfish and dollar bills. sand. Digital nomads will appreciate the smart computer desk setup and Keurig coffee machine; vacationers will appreciate the library filled with board games and beach reads (think Danielle Steel and John Grisham). Bonus points for Puracy eco-friendly toiletries.
The plunge pool in this Airbnb penthouse features a spa-like waterfall.
Courtesy of Airbnb/Barry Fitzgerald
3 bedroom penthouse on Duval Street
- Sleeping: 8
- Strong points: Heated swimming pool, hammock, large kitchen
- Book now: From $788 per night, airbnb.com
Spanning over 2,200 square feet of living space and an additional 2,000 square feet of porches and terraces, this elegant two-story 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 opposite. 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 terrace to a plunge pool deep lined with palm trees with a spa-like waterfall. Ideal for large groups, the space includes an outdoor dining table that seats eight, a crib, washer and dryer.
Anyone booking an extended trip to Key West will benefit from this Airbnb’s spacious kitchen.
Courtesy of Airbnb/Jenna Beldyga
Beachfront Beach Club Condo
- Sleeping: 4
- Strong points: Two swimming pools, tennis court, fitness center
- Book now: From $828 per night, airbnb.com
Away from the scrum of historic Old Town, the Mid-Town neighborhood offers a beachfront respite that’s more residential than rowdy. This two-bedroom Key West Beach Club unit will make you feel like a local, thanks to condo resort amenities that include two swimming pools, a tennis court, fitness center, sauna, and communal outdoor kitchen area. Inside, you’ll find yourself gravitating towards the spacious kitchen, with its large island perfect for preparing fresh seafood or mixing up a fruity cocktail, while the expansive balcony overlooks swaying palm trees and a quiet part of the house. ‘Atlantic Ocean.
At the time of publication, these Airbnbs all have an overall rating of 4.90 or higher and all positive reviews from previous guests.
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