Key West Vacation Rentals
Key West vacation rentals offer a vibrant island escape with a mix of historic homes, charming cottages, and modern condos designed for comfort and convenience. Choose from Key West vacation homes featuring multiple bedrooms, full kitchens, private pools, and outdoor living spaces—ideal for couples, families, and group getaways. Many Key West rentals include sought-after amenities such as walkable locations, private courtyards, and easy access to beaches, marinas, and local attractions.
Located at the southernmost point of the Florida Keys, Key West blends laid-back island living with a lively atmosphere unlike anywhere else in the Keys. Known for its colorful architecture, rich history, and energetic culture, Key West offers something for every type of traveler—from waterfront relaxation to dining, shopping, and entertainment. With a variety of accommodations in Old Town, near the harbor, and throughout the island, Key West vacation rentals provide a unique and memorable stay.
Why Stay in Key West?
Key West offers a one-of-a-kind experience, combining tropical beauty with a vibrant local scene. Guests can spend their days exploring historic streets, relaxing by the water, or heading out on boating and fishing excursions, then enjoy evenings filled with live music, waterfront dining, and sunset views.
Unlike other areas of the Florida Keys, Key West is highly walkable and bike-friendly, making it easy to explore without a car. From quiet residential pockets to lively areas near the heart of town, there’s a range of settings to match every travel style.
Unique Homes & Island Living
Key West vacation rentals are known for their character and charm. From restored conch houses and classic cottages to modern condos and private estates, each home offers a distinct sense of place. Many properties feature lush tropical landscaping, private pools, and inviting outdoor spaces designed for relaxing in the island climate.
Whether you’re enjoying a morning coffee in a shaded courtyard or unwinding after a day of exploring, these homes provide a comfortable retreat in the middle of one of the most unique destinations in the country.
Plan Your Key West Getaway
From historic landmarks and waterfront adventures to unforgettable sunsets and a lively local culture, Key West offers an experience unlike anywhere else in the Florida Keys. With a wide range of accommodations and a setting that blends relaxation with energy, Key West vacation rentals provide the perfect home base for your next island escape.
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84 properties available
Welcome to a rare luxury oceanfront estate in the Florida Keys, offering total privacy, panoramic water views, and resort-style amenities, just 18 miles from Key West. This exclusive waterfront compound is more than a vacation home—it’s a private destination designed for luxury travelers, milestone celebrations, and unforgettable coasta
Slip into island time at this one-bedroom, one-bath condo for four in Key West, where you'll have entertainment and nearby beach access in an awesome central location. Sitting right downtown on Simonton Street, you're one street over from all the restaurants and bars on Duval, and within easy walking or biking distance from all the main att
Boasting stunning sunset vistas second only to Mallory Square and a convenient location for cruising to Key West attractions, this four-bedroom home offers a private slice of paradise on Stock Island. This prime bayfront property showcases bespoke features, including a 40-foot dock, sun deck, and custom-built tiki lounge with a built-in TV and outd
Take a remarkable retreat to Key West with this one-bedroom, one-bathroom cottage with a shared pool, and a great central location on the island! Sitting in a quiet location just off Truman Avenue and a few blocks down from Duval Street, you'll be within walking distance of any number of delicious restaurants, not to mention famous historical a
*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 dog-friendly cottage includes street parking, a shared pool, and a location near Duval Street.Nestled in a quiet neighborhood about a mile from Higgs Beach Dog Park and a little under a mile to Mall
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
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
Plan your next getaway to this quaint tropical studio, complete with a well-equipped kitchenette, furnished patio, and access to a swimming pool, well-maintained tropical courtyard, and sundeck. This complex is located in a quiet, residential neighborhood, and street parking is available during your stay.Walk two blocks to the southernmost beach fo
Situated in the heart of Key West, this unbelievable retreat will be the perfect place for entertaining the whole family! With three stories, high-end furnishings, and ample areas to spread out, there will ample room for everyone to indulge in their own kind of vacation. As if that isn't enough, recent renovations to enhance your stay include n
Find your own little piece of paradise at Tarpon Watch, a waterfront escape offering gorgeous views of the Gulf of Mexico, plenty of room for you and your loved ones to relax, and an ideal location close to Key West's most beloved attractions. At the end of each beautiful day, mix up a favorite beverage at the wet bar, step out onto the large b
This Key West condo boasts deluxe amenities like a shared outdoor pool, a hot tub, tennis courts, and a fitness room. It has everything you need for a memorable Florida Keys getaway!Located right near the water, you'll be in a prime spot to sample all of the island's many charms. Easily walk or bike to popular Smathers Beach, a great place to rent
Prime Key West Location Escape to laid-back island living in this inviting Key West retreat, where tropical beauty and everyday comfort come together seamlessly. Tucked away in a quiet, greenery-filled neighborhood, this single-story home offers a peaceful setting while keeping you close to everything that makes Key West unforgettable. Step outside
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