Vacation Rentals
50 properties available
Chicken Water Cabana at Custom House Inn
Located in the heart of vibrant Duval Street, Chicken Water Cabana at Custom House Inn offers the ultimate Key West experience with two beautifully designed, modern, adjacent suites, Underwater Cabana and Chicken Run. Just steps from the island’s best bars, restaurants, and attractions, these colorful, fres
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 Space:
Kingfish Keep | Lively Escape on Duval! Balcony!
Kingfish Keep is the perfect escape in the heart of the historic district! This charming flat features an upstairs balcony that offers lovely views of the Duval Street, just steps away from shopping, dining, and the beach.
The Space:
Kingfish Keep comfortably accommodates up to four guests, ideal f
The Salt Cay | Updated! Stunning Sunset View, Pool!
Escape to The Salt Cay, a serene, beautifully updated, and well-appointed 2-bedroom condo nestled in the tranquil Sunrise Suites community on east side of Key West. Just a mile from the beach, this charming getaway offers the ideal combination of relaxation and adventure. Whether you\'re lounging
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
Welcome to Harborwalk Hideaways!
Overview:
Discover Harbor Walk Hideaways, a beautifully renovated vacation rental complex nestled in the Historic Seaport district of Old Town Key West. This sought-after destination features three charming cottages—Atocha, Pilar, and African Queen—each named after legendary vessels that frequented Key West. Ideal
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
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
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
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
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
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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