Key West, Florida


Properties Available 151 properties available
Featuring its own backyard oasis, this two-story retreat invites you to experience the best of island living right at home. Surrounded by lush landscaping, the fenced backyard features a private heated pool with a waterfall as well as an outdoor seating area where you can dine alfresco or sip cocktails in the sun. When you're ready to venture from
Let's Flamingo (277126)
Key West, FL
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Welcome to Julia Whitehead Guest Suites! Built in the 1890s on the site of what had been a small provisions and butcher shop, this charming building has a rich and captivating history. In the 1930s, while Hemingway was living a few houses down, it was home to a popular Cuban bodega. From the 1980s through the turn of this century, potter Charles Pe
Julia Whitehead Guest Suites (575214)
Key West, FL
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Let year-round warm breezes transport you to deep relaxation at this three-bedroom, three-bathroom Key West vacation rental. The home's great amenities include a shared pool, a gym, and plenty of space for up to six guests! This home is located on Stock Island, which is between Key West and Boca Chica Key. It's a short drive south to world-fam
Hemingway Hideaway (273980)
Key West, FL
House
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This simple, modern cottage apartment is an ideal space for a couple or a solo traveler looking to explore the heart of Key West! The contemporary living space will ensure your ease and comfort during yo
Borrowed Time (246414)
Key West, FL
House
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Bask in the peaceful sunshine of Key West and feel all your stress melt away when you stay at this cozy dog-friendly cottage right in town. With a private hot tub in the garden area out back plus all the conveniences of home, what's not to love? Sitting only half a block from all the fun and excitement of Duval Street, park your car in the private
Leeward Isle (251522)
Key West, FL
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Beautifully situated among the palms and right on a canal that leads out to open water, this three-bedroom home on Big Coppitt Key is the perfect Florida Keys escape for boating enthusiasts, anglers, and families and friends in search of waterfront relaxation. This single-story home provides a canal-front dock where you can park your boat, two kaya
Sapphire Sabbatical (258532)
Key West, FL
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Experience Key West in style with this lovely vacation rental in the heart of Old Town! Up to six guests will enjoy a private hot tub and typical home comforts including a private washer/dryer, street parking, and free WiFi. Situated just one block from Duval Street, this cottage has no shortage of activities nearby. Sample some of the local restau
Conch Casa (274147)
Key West, FL
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
This romantic suite provides everything you need for a couple's getaway in Key West. This home's coveted location on Duval Street means prime access to the town's best nightlife and restaurants only a few blocks away. You're also a short walk from the beach; Southernmost Point is about four blocks down. Make meals at home with the kitchenette's fri
Wahoo Way On Duval (245729)
Key West, FL
House Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rustle up your favorite people for a memorable trip to Key West with these two homey cottages. Sitting side-by-side in a great location, each house features two bedrooms and one bathroom, a private parking space, dog-friendly accommodations, and a tranquil garden with a private hot tub in the back - what's not to love? Located half a block from all
Tradewinds (245768)
Key West, FL
House Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 12 guests
Get away from the stress of the daily grind with a trip to this contemporary Key West home. Offering street parking, access to a shared pool, room for up to four guests, and a charming island-themed ambiance, this home will make it easy to slip into vacation mode. The family dog is also welcome to join you here for an additional nightly fee. Set i
Tropical Village Retreat (243539)
Key West, FL
House Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
*Please note that this home only allows minimum night stays of 28 nights or longer. This is enforced by the HOA and we cannot make any exceptions. This cozy-yet-modern cottage apartment in Key West is a wonderful escape for any party of two! A flatscreen TV in the living room allows you to unwind with your favorite movies and shows, and the full co
Bottoms Up (257153)
Key West, FL
House
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Enjoy this one bedroom apartment for your next getaway to Key West! Perfect for couples, this romantic spot is newly remodeled and will provide everything you need for a quick weekend escape! Beach towels are provided for your use. What's nearby: Located in the heart of downtown, you'll be just steps away from Duval Street. Within walking distance,
Truman @ Duval - Unit B (244958)
Key West, FL
House
Bedrooms 1 bedrooms
Bathrooms 2 baths
Guests 4 guests

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