Karyn Wofford is a freelance writer in the fields of travel, eco-tourism, and wellness. She’s an avid traveler and Georgia native. She grew up with a passion for travel, exploring everything from the mountains to the ocean, and continues to find new and unique things to do in the places she travels.
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Key West is not only a tropical paradise that you don’t have to board a plane to reach, but it’s teeming with exciting attractions, from historical sites and trendy restaurants to a pleasant nightlife. Craving days of snorkeling, biking downtown, eating key lime pie and shrimp? Consider renting an Airbnb to totally immerse yourself in the Key West way of life. Many require a 28-night stay to comply with the Homeowners Association, but that’s a great excuse to stay and play for a while. From quaint little pools to airy pastel aesthetics, these are our favorite Key West Airbnbs.
Outdoor spaces at this dog-friendly, dual-level home are something out of a dream, with elevated porches and other cozy patio space with hammocks to lounge. Let’s not forget the perfectly “Key West” pint-sized pool out back, which is surrounded by tables, umbrellas and swaying palms. Inside is modern and fresh, with a variance of sleeping arrangements, from rooms with twin-sized mattresses to king and queen-sized beds. With all the amenities from home, including a washer and dryer, it would be a piece of cake to meet the 28-night requirement.
Walk to one of the few swimmable beaches on the island from this bright condominium, which accommodates up to three guests quite comfortably. In addition to the vibrant interior space, you’ll find a breezy porch with cushy loungers, and an inviting pool available to the complex. Mallory Square is just around the corner, while Zachary Taylor Park is a short walk away, where you can swim, snorkel or hang out in the hammocks at the beach.
Looking for something a bit out of the bustle of it all? This Airbnb is perfect for you. Bird of Paradise is nestled in a quiet neighborhood and features its own fenced-in backyard oasis. The pool is significantly larger than most you’ll find among Airbnb locations in Key West, and the floor-to-ceiling French doors connect the indoor living room to the beautiful outdoor area. Six guests can easily bunk up within the tropical-chic haven.
Wood trim and flooring give this duplex a tropical vibe. But the best part of this one-bedroom listing is the sandy beachfront! On a key where most have to get on a boat to have the best water access, this is an awesome feature. Enjoy the amenities and plenty of great views. This is a wonderfully romantic pick, also conveniently located near restaurants and shops.
It’s bright, it’s colorful, it’s very Key West! Cleanly decorated, the condo still manages to exude a lot of personality. The location is highly walkable, so guests can do a hefty amount of sightseeing. The Southernmost Point and Hemingway House are both proximal attractions. And if you don’t feel like walking, bikes and scooters are available to rent.
Way better than a hotel room, and far less expensive than renting an entire house, this room at Andrews Inn is nothing short of dreamy. Subtle tropical decor gives the room some flair, and the bathroom is lovely. A private terrace allows for the perfect spot to enjoy the bustling streets of Key West. Enjoy cinnamon rolls in the morning, and all the mimosas you can drink, both included in the rate.
What more could you need, than this tiny one-bedroom cottage nestled within Old Town? Well, the hosts thought you would need a complete oasis as well. Outside you’ll find a pristine grilling area amongst the most gorgeous naturalistic pool. There’s even a small washer and dryer to take care of laundry!
What used to serve as a cistern in the 1800s, is now a precious studio cottage with plenty of amenities. Inside is adorned with Caribbean flair and a baby blue hue, which definitely makes guests feel like they are in the heart of Key West. Grab a bike, and pedal the surrounding area to see some of the things that make Key West famous.
Luxury blends seamlessly with Key West authenticity. Stunning tile floors, sleek wooden ceilings and walls, and French doors that reveal a tranquil pool and deck all come together to create one heck of a tropical escape. With all of the necessities a home provides, you could literally have the best staycation with eight of your closest friends.
Cute is the theme at this little nook near Duval Street. Inside is compact, yet efficient, with a small kitchen space and plenty of spots to relax. Fall in love with the private deck complete with jacuzzi! This is another wonderful option for solo travelers, couples, or best friends.
Offering a quiet and secluded room with a private entrance, you can experience an authentic Key West getaway at this Airbnb. The pool, which guests have private access to is surrounded by a mango tree and rich planked wood decking. A Keurig coffee maker and tea kettle with a selection of coffee and teas await alongside a convenient mini-fridge. Lounge in comfy chairs and enjoy this secluded oasis, then access the heart of Old Town on the other side of the foliage or head to the beach with your complimentary beach towels. Duval Street is just minutes away by foot, as are the best eateries in Key West.
Baby blue and snug as bug, this wee cottage sits right beside Duval Street. Inside you’ll find a kitchen, bath, living area and one bedroom, which create more than enough space for vacationers. While you won’t find a pool, the location amongst some of the more notable spots in Key Kest by far makes up for it. Opt for a snorkeling day cruise or sample the best Key Lime pie in Key West instead!