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
Ideal for a small group or two couples traveling together and looking for a private, amenity-rich experience, this cozy second-floor tropical studio offers a well-equipped kitchenette, a furnished deck, and access to a swimming pool at the heart of a beautifully maintained tropical courtyard.Located two blocks from the southernmost beach and one bl
Relax under azure skies and the gently rustling fronds of palm trees when you stay at this elegant and dog-friendly Key West condo! A community pool and hot tub, tennis courts, a parking space, and pool views from your private balcony add to an atmosphere of luxury and total relaxation.This rental is part of the upscale Sunrise Suites Resort, locat
Spend your vacation days snorkeling in the clear coastal waters and strolling the streets of downtown Key West when you stay at this three-bedroom, two-bathroom cottage, which also features a private hot tub and one reserved off-street parking space. The family dog is also welcome to join you for an additional nightly fee. This cottage's locati
Welcome to Julia Whitehead Lighthouse 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 Charl
Treat your family to an unforgettable stay in Key West with this dog-friendly condo. Modern conveniences combine with a great location and first-class resort amenities - you'll love this adventure so much, you'll never want to head back home!When you're done swimming in the shared pool or soaking in the shared hot tub, you can towel off and head in
Enjoy a soak in your own private, heated saltwater pool at this lovely duplex! Part of the Tropical Vibes home, this duplex is a charming hideaway with plenty of room to hang out. Open the sizable glass sliding door to create a seamless indoor/outdoor space between the kitchen, living room, and pool deck. Grill up something tasty on the private gas
Looking for a place in sunny Key West where your whole group can bask in the pleasures of island life without sacrificing privacy? This complex of three condos is your ticket - featuring entertainment, private parking, and beach access nearby, you'll have everything you could hope for on a tropical vacation!Sitting only one block from the central a
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
Caribbean comforts await at this lovely Key West condo just five miles from the island's historic downtown. With amenities like a private pool and hot tub, tennis courts, a private balcony, and a covered parking spot, this comfortable condo is perfect for anyone who plans to explore the island by day and relax peacefully at night.Located on the eas
*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
This home is just perfect for your Keys getaway! The open floor plan and well-appointed kitchen will make your stay more than comfortable. French doors off the living room and primary bedroom offer beautiful views of the private pool and the lush tropical landscape in the enclosed yard. You will enjoy the private outdoor living area, including the
This second-floor tropical studio has a private outdoor seating area and plenty of space for your vacation crew. Spend time splashing in the shared pool or catch some rays on the sundeck.Located in a residential neighborhood two blocks from the southernmost beach and just one block from Duval Street for the area's best restaurants, shops, terrific
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