Vacation Rentals
50 properties available
Experience the vibrant charm of Key West with a stay at Sea Esta Suite, a stunning two-story townhouse located in the exclusive Duval Square condominium complex. Perfectly situated at the intersection of Truman Avenue and Duval Street, this vacation rental puts you just steps away from world-class dining, shopping, and iconic attractions like the S
Cat Island Suite | Updated! Stunning Sunset View, Pool!
Escape to Cat Island Suite, a serene, beautifully updated, and well-appointed 2-bedroom condo located in the peaceful Sunrise Suites community on the east side of Key West. Just a mile from the beach, this charming getaway provides the perfect combination of relaxation and adventure. Whether
Butterfly Nest | Newly Updated w/ Shared Pool
Escape to Butterfly Nest, a serene, beautifully designed 2-bedroom condo located in the tranquil Sunrise Suites community on the southeast side of Key West. Just a mile from the pristine beach and a quick 10-minute ride to the lively Duval Street, Butterfly Nest offers the perfect blend of relaxation a
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
Birds of a Feather at Custom House Inn | Vibrant Stay on Duval Street!
Discover the heart of Key West at Birds of a Feather, one of five uniquely themed suites at the Custom House Inn, right on famous Duval Street. This bright and colorful hideaway offers modern comforts and a fun, edgy design, providing the perfect base for your island adventure.
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
Seagull Suite | Inviting Studio, Just Steps From Duval, Hot Tubs!
Seagull Suite is the perfect choice for your next getaway in Key West! This cozy suite is part of Southernmost Sanctuary, offering easy access to shared hot tubs and a charming patio to soak up the island atmosphere. Equipped with a kitchenette, cable TV, and complimentary WiFi, you
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
Sunshine State at Custom House Inn | Bright Studio on Duval Street!
Welcome to Sunshine State, your vibrant Key West escape at the Custom House Inn. Located in the heart of historic Duval Street, this modern, colorful studio is part of a five-unit boutique complex designed to reflect the lively energy and rich culture of the island. Whether you’re
Carey’s Corner | Updated Studio with Heated Pool
Carey’s Corner is a cozy, updated studio nestled in the heart of Bahama Village. Key West may be small, but its magic is immense, and Carey’s Corner is the perfect base for experiencing it all—from the relaxing poolside to the lively nearby attractions.
The Space:
This second-floor studio features
Southernmost Sanctuary | Vibrant Oasis Near Duval! Perfect for Groups!
Southernmost Sanctuary is the ideal destination for your next group getaway in Key West! This lively property boasts three private hot tubs, spacious decks, multiple kitchenettes, and six bedrooms that can accommodate up to 24 guests.
The Space:
Southernmost Sanctuary features
Ibis Suite | Bright Hideaway, Hot Tubs, Steps from Duval!
Ibis Suite is an excellent choice for your next getaway in Key West! This welcoming suite is part of Southernmost Sanctuary, offering easy access to shared hot tubs and a lovely patio to soak up the island atmosphere. Equipped with a kitchenette, cable TV, and complimentary WiFi, you’ll fee
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