Key West ticks all the boxes. Tropical beaches, check. Spirited nightlife, check. Sweet yet tart dessert, check. World-class snorkeling and diving, big tick. To top it all off, the island city is abundant with luxurious vacation rentals where you can recharge. Rather than take our word for it, experience all this for yourself with a Key West Airbnb.
Photo: Airbnb
11 Key West Airbnbs to Experience the Best of the Island
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We hope you love the Key West Airbnb rentals we recommend! Just so you know, Matador may collect a small commission from the links on this page if you decide to book a stay. Listed prices are accurate as of the time of publication.
- Beautiful Key West Airbnbs with pool
- Unique Key West Airbnbs on the water
- Common questions about Key West
Beautiful Key West Airbnbs with pool
Downtown Key West Airbnb loft with pool
Designed in Key West’s ‘conch cottage’ style, this restored heritage property gushes warmth and character through its colorful furnishings and décor. With three spacious double rooms, this property is suited to families and small groups. A tranquil garden is shrouded with greenery and features a pool and propane barbecue. Located in the Key West Historic District, all the sights are within walking or cycling distance.
Four guests, one bedroom
Price: $457 per night
Seaside Place
Complete with lavish balconies and gingerbread trim, Seaside Place is your quintessential Key West home. A sunlit lounge marks the heart of the house, leading into an open-plan kitchen that overlooks the backyard. The landscaped pool comes with a waterfall and a maximum depth of 7 feet so you can safely perfect your dives. Look forward to a post-swim shower in the cabana bathroom before tucking into a gourmet grill with the property barbecue. This Airbnb near Duval Street Key West is moments from the downtown restaurants and nightlife.
Ten guests, five bedrooms
Price: $1,900 per night
Large family Airbnb with pool in downtown Key West
Situated in the historic heart of Key West, this rose-hued blends beautiful aesthetics with contemporary luxury and an unbeatable location. Choose a bedroom at the front and benefit from a private balcony or sleep at the rear and wake up to pool and garden views. Consisting of five ample guest rooms, five bathrooms, and countless communal areas, this Key West Airbnb with pool strikes a harmony between downtime and socializing.
Sixteen guests, nince bedrooms
Price: $2,226 per night
Southard Comfort Airbnb with pool and historic charm
Designed to maximize calmness and comfort, this Key West Airbnb consists of homely interiors and an oh-so-Instagrammable backyard. Spend your day circulating from the cocktail pool to the sun lounger before firing up the barbecue for an alfresco dinner. Situated in the laid-back Meadows neighborhood, you’re not far from Duval Street and the marina.
Six guests, three bedrooms
Price: $1,200 per night
Maisons de Luxe
Maisons de Luxe comprises the villa, Grand Maison, and a self-contained cottage, Petite Maison. Both buildings are spread over two levels and offer a total of six en-suite bedrooms. Rigged out with a large open-plan lounge/kitchen, saline swimming pool, sun deck, and front porch there’s plenty of space for social butterflies. This luxurious Airbnb at Duval Street Key West is within walking distance of the best cafes, nightclubs, and tourist attractions in town.
Twelve guests, six bedrooms
Price: $2,000 per night
Unique Key West Airbnbs on the water
The Grand Tiki Airbnb at Key West
Glamping gets an aquatic makeover at this Airbnb Tiki Suite Key West. This floating cabana consists of a simple dwelling space fitted with an en suite bathroom and ocean views galore. French sliding doors open out onto your veranda where you can meditate to the sound of the waves and keep a lazy eye out for dolphins. Renting the Tiki cabin includes two inflatable paddleboards and two snorkel sets. This more than makes up for the limited Wi-Fi while you surrender yourself to an off-grid experience free of Netflix and TikTok. Do we even need to mention the potential for sunrises and sunsets? No need to weep into your rum if the Tiki Suite is unavailable. Check into its twin instead – the OG Tiki Suite.
Two guests, one bedroom
Price: $650 per night
Hidden Beach Duplex with sea views
If you’re hankering for the castaway experience without sacrificing your creature comforts, this beachfront condo has the answers. The two-story house overlooks a private sandy beach fringed with palm trees. Wake up to sunrises from your private veranda and take romantic golden hour walks along the bay. Located in the quietest part of Key West, the Hidden Beach Duplex is exactly what you need for a romantic seaside getaway.
Two guests, one bedroom
Price: $600 per night
Luxury Yacht Airbnb moored just off Key West
All aboard the Maruquis – a massive sailing yacht with sleek interiors to make a 5-star hotel blush. Teak and mahogany cabins await you with a modern bathroom and fully-equipped kitchen. When the sun’s out (which, in Key West, it generally always is) you can lounge on the deck with a mojito. Docked in one of the prettiest marinas in Key West you will benefit from all areas of the gated facilities including a clubhouse, swimming pool, and private beach. This Airbnb Key West houseboat is suitable for a couple or a family of three.
Six guests, three bedrooms
Price: $289 per night
Tranquilo – Key West Luxury Houseboat
This cushy Airbnb Key West houseboat is spread over three floors of luxury. A granite-clad kitchen and internal lounge culminate in the open-air deck where you can soak up panoramic views with your nearest and dearest. The floating home comprises two double bedrooms plus a sofa bed in the lounge. Located at Stock Island Yacht Club, the boat is a 15-minute drive downtown. You are welcome to use the club’s pool, private beach, gym, and oceanside tiki throughout your stay.
Six guests, two bedrooms
Price: $750 per night
Catamaran Airbnb in the Key West waters
Ahoy there, aspiring seafarers! This Key West Airbnb on the water is reserved for the most adventurous as you cast off and take to the high seas. Equipped with three separate bedrooms and an internal salon, there’s plenty of space to avoid the onset of cabin fever. Feel the warm ocean breeze in your hair as your captain steers you far from the hustle of downtown and into open water where you snorkel, paddle, and plunder the champagne cooler to your heart’s content.
Six guests, three bedrooms
Price: $1,700 per night
Airbnb apartment perfect for long-term stays
Who wouldn’t want to commit to a month in this tropical island city? Buried beneath lush greenery, this Airbnb in Key West Florida is an oasis that you can call home (for a minimum of 28 days). In addition to the main building, the place features a separate cottage with one bedroom. Opulent touches include a cedar hot tub, an outdoor shower, and a lanai that peers over the private pool. Despite evoking a sense of remoteness, the villa is a short drive or cycle ride from Duval Street and the beaches.
Eight guests, four bedrooms
Price: $900 per night
>h2>Is Airbnb legal in Key West?
Yes, short-term rentals through Airbnb and other platforms are legal in Key West, Florida, but they are regulated and require permits to operate. According to the city’s code of ordinances, residential properties may be rented for less than 28 days, but property owners must obtain a transient rental license and meet certain requirements, such as building inspections, insurance, and paying lodging taxes.
How far is Key West from Miami?
Key West is approximately 160 miles away from Miami, and it takes about three and a half to four hours to get there by car, depending on traffic conditions. The most popular route to Key West is the scenic Overseas Highway, which is a part of U.S. Route 1 and stretches from Florida City to Key West.
If you don’t have a car, you can take a bus from Miami to Key West; Greyhound and Miami-Dade Transit have daily scheduled services. Alternatively, you can take a ferry from Miami to Key West, which is a great way to enjoy the scenic beauty of the Florida Keys. The ferry ride generally takes about three and a half hours, and several companies offer this service. The Key West Express is a popular ferry service provider with daily departures from Miami and Fort Myers Beach.
Where should I stay in Key West
Key West offers a wide range of accommodation options, from luxurious resorts to cozy bed and breakfasts. The right choice for you may depend on the purpose of your visit, your budget, and personal preferences. However, some popular neighborhoods to consider for a great Key West experience are:
Old Town: This is the historic part of Key West, filled with beautiful architecture, galleries, cafes, and restaurants. Staying in Old Town will give you easy access to most of the city’s main attractions.
Duval Street: This is the main commercial street in Key West, known for its vibrant nightlife, boutiques, bars, and cafes. Staying on or near Duval Street allows you to be at the center of the action.
Casa Marina: If you prefer a more secluded beach vacation, Casa Marina is an excellent option. It is located a few minutes away from Old Town and offers a private beachfront, two swimming pools, and lush gardens.
Truman Annex: This upscale neighborhood boasts lovely homes and condos. It’s just a few short blocks from all the action on Duval Street and Mallory Square, but it’s quiet and peaceful at night.
Stock Island: For a more rustic and laid-back vibe, Stock Island is a great option. It is home to many interesting art galleries, marinas, fishing charters, and restaurants, and a perfect stay if you are looking for an island getaway. 