Vacation Rentals
59 properties available
Welcome to Pilar Cottage, a charming studio located within the peaceful Harbor Walk Hideaways complex in Key West\'s Historic Seaport district. This cozy one-bedroom, one-bathroom retreat features upscale furnishings and offers a small shared dipping pool, making it a perfect spot to soak up the Florida sun.
Comfort and Amenities:
Pilar Cottage is
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.
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
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
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
Casa Bonita | Stylish Condo with Pool, Gardens & Prime Old Town Location
Casa Bonita is your ideal home base for exploring the best of Old Town Key West! Nestled just steps from vibrant Duval Street, this spacious condo offers a perfect blend of comfort, style, and tropical charm. With lush gardens, a relaxing pool, and pleasant décor, this vacati
Truman @ Duval - Unit D | Two-Bedroom with Full Kitchen & Prime Location
Welcome to your perfect family getaway in the heart of Key West! This charming two-bedroom, one-bathroom offers a wonderful combination of comfort, convenience, and prime location for your next vacation. Just a half block from the lively Duval Street, you\'ll be steps away fr
The Samana Cay | Tropial, Airy Retreat w/ Private Balcony & Pool!
Escape to The Samana Cay, a bright and inviting 2-bedroom vacation home that offers the perfect blend of relaxation and adventure in Key West. Located just minutes from the island\'s top attractions, this cozy retreat provides a peaceful oasis with all the comforts of home. Whether
Chagall\'s Corner | Newly Remodeled!
Chagall\'s Corner offers a relaxing, second-floor retreat in the heart of Key West. This newly remodeled micro-efficiency is perfect for those seeking a serene escape while still being close to all that makes Key West magical and unique.
The Space:
This studio features a Queen bed, en-suite bathroom, and a ki
Truman @ Duval Unit B | Ideal One-Bedroom Retreat for Couples
Escape to a charming one-bedroom apartment in the heart of Key West, the perfect spot for a romantic retreat or a weekend getaway. Recently remodeled with comfort and style in mind, this apartment offers all the essentials for a relaxing and memorable stay. Whether you\'re here to explo
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.
The Sp
Escape to the vibrant heart of Key West and stay at the charming Claude Monet Suite, located just a few blocks from famous Duval Street. This micro-efficiency studio offers a cozy retreat for up to four guests, with access to a tranquil pool and spacious sundeck. Once a creative hub for traveling artists, The Galleria has now been transformed into
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