Nightly properties
42 properties available
Underwater Cabana at Custom House Inn | Stay on Duval Street!
Experience the heart of Key West with a stay at the Underwater Cabana, one of five uniquely designed suites at the Custom House Inn. Nestled on the iconic Duval Street, this aquatic-themed suite offers the perfect blend of comfort, style, and location. Whether you’re here to explore the
Chicken Run at Custom House Inn | Stay on Duval Street!
Welcome to Chicken Run, a vibrant and uniquely themed studio located at the Custom House Inn—right in the heart of historic Duval Street. This newly remodeled studio offers modern, edgy design with a splash of bright green, perfectly complementing the colorful atmosphere of Key West. Whether
Duval Street Retreat | Dog-Friendly Home with Hot Tub, WiFi, & Private Parking
Duval Street Retreat is your ideal Key West escape, perfectly situated in the heart of the island’s historic district! With a shared hot tub, patio space for grilling, and easy access to the best of Key West, this home offers the perfect mix of comfort and convenience.
Citrus Queen at Custom House Inn | On Duval St! | Bright & Modern Studio
Welcome to Citrus Queen, your vibrant, modern escape in the heart of Key West! Located at the Custom House Inn on the iconic Duval Street, this newly remodeled studio is perfect for a fun and comfortable stay. Each unit in this charming five-apartment complex is uniquely desi
Andy’s Attic | Budget-Friendly!
Andy’s Attic is an affordable, cozy studio designed for two guests. Located in Bahama Village, this budget-friendly rental offers easy access to Key West’s most famous sights. Key West may be small, but the experiences you’ll have here are grand—and Andy’s Attic provides a perfect place to enjoy it all.
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Southernmost Retreat | Two Dog-Friendly Homes with Hot Tubs, WiFi, & Private Parking
Southernmost Retreat is the perfect home base for your Key West getaway! Comprising two beautifully appointed homes located in the heart of Key West’s vibrant historic district, this combined property offers the ideal mix of comfort, convenience, and relaxation. W
Pelican Suite | Cozy Cottage, Hot Tubs, Close to Duval!
Pelican Suite is the ideal spot for your next getaway in Key West! This inviting suite is part of the Southernmost Sanctuary, providing easy access to shared hot tubs and a lovely outdoor patio perfect for soaking in the island ambiance. With a kitchenette, cable TV, and complimentary WiFi, y
Duval Hideaway | Dog-Friendly Home with Shared Hot Tub, Patio & Prime Location
Duval Hideaway is the perfect home base for your island getaway! Located in the heart of Key West’s on Duval Street, this charming home offers a relaxing shared hot tub, a patio with a grill, and dog-friendly accommodations—just two blocks from the beach at Fort Zachary
Meadows Manor | Elegant Oasis with Private Pool & Parking
Discover the perfect blend of luxury and tranquility at the Mansion in the Meadows, a beautifully landscaped 4-bedroom, 4-bathroom haven in the heart of Key West. This stunning home features a private pool surrounded by lush greenery, providing an ideal oasis for families or groups seeking
The Andros | Incredible Views w/ Shared Pool
Escape to The Andros, a serene, beautifully designed 2-bedroom, 2-bath condo nestled in the tranquil Sunrise Suites community on the southeast side of Key West. Just a mile from the beach with its stunning aqua-blue waters and loungers, this charming retreat offers the perfect mix of relaxation and adve
Welcome to African Queen Cottage, a charming retreat within the serene Harbor Walk Hideaways complex in Key West\'s Historic Seaport district. This inviting one-bedroom, one-bathroom cottage combines modern comforts with a prime location, perfect for enjoying the local attractions and beautiful waterfront.
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African Queen Cotta
Osprey Suite | Charming Hideaway, Hot Tubs, Close to Duval!
Osprey Suite is the perfect choice for your next getaway in Key West! This charming suite is part of Southernmost Sanctuary, offering easy access to shared hot tubs and a delightful patio to soak up the island atmosphere. Equipped with a kitchenette, cable TV, and complimentary WiFi, you’
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