Vacation Rentals
61 properties available
Garden of Roses | Private Hot Tub, Prime Key West Location!
Experience the essence of Key West living at Garden of Roses, a beautifully restored conch-style home in a fantastic location. Just a block away from Duval Street, this monthly rental offers the perfect retreat for those looking to enjoy both comfort and convenience. With a private hot tu
Conch Cove | Heated Pool & Prime Location!
Conch Cove is your private oasis in Old Town Key West! This 3-bedroom, 3-bathroom retreat, just one block from bustling Duval Street, offers the perfect balance of luxury, comfort, and charm. Nestled within Key West\'s enchanting surroundings, Conch Cove ensures everyone can experience the magic of the is
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.
Comfort and Amenities:
African Queen Cotta
Charming 2-Bedroom Retreat with Golf Course Views | Key West Golf Club Community
Nestled in the picturesque Key West Golf Club community, this charming 2-bedroom, 1.5-bath home offers the perfect combination of tropical serenity and modern convenience. Surrounded by lush landscaping and featuring beautiful views of the adjacent golf course, this t
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 fe
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
Casa De Cubana | New! Historic Cuban-Style Home Steps from Duval Street
Discover the charm and elegance of Key West at Casa De Cubana, a newly constructed 2-bedroom, 2.5-bathroom home that blends the rich history of Old Town with modern comforts. Located just half a block off the iconic Duval Street, this single-story elevated home draws inspirati
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
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
Feather Queen at Custom House Inn: A Key West Gem on Duval Street
Located in the vibrant heart of Duval Street, Feather Queen at Custom House Inn offers the perfect combination of colorful charm and modern convenience. These newly renovated, stylish, adjacent suites, Citrus Queen and Birds of a Feather, are just steps away from the best Key West h
Duval Delight | Recently Remodeled Condo on Duval!
Duval Delight is your gateway to enjoying the best of Key West! Located on the quieter end of iconic Duval Street, this beautifully remodeled loft-style condo offers the ideal setting for a tropical getaway. Whether you\'re here for the culture, cuisine, or the famous sunsets, Key West\'s magic is
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
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