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2026-03-22
2026-03-23
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Key West holiday rentals

Grand Marina Suite -Waterfront Condo

Peninsular Avenue 6000, Key West, United States View map

**Discover Tranquility at Grand Marina Suites** More

From US$ 325 Book Now

Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking

Seaside Drive 3625, Key West, United States View map

Set at a 4.9 km distance from The Ernest Hemingway Home and Museum and nearly 20 minutes' walk from State Harbor, the 2-bedroom Tortuga Suite 301 is located in Key West. A full kitchen with a… More

From US$ 595 Book Now

Truman @ Duval

Key West, United States View map

Nestled in the vibrant heart of Duval Street, Truman @ Duval invites guests to indulge in the quintessential Key West experience. More

From US$ 210 Book Now

Leeward Isle

Key West, United States View map

Nestled in the vibrant heart of Key West, Leeward Isle impressively combines casual elegance with modern comforts. More

From US$ 423 Book Now

Sea Breeze -Great Location!

Whitehead Street 1025, Key West, United States View map

The 2-bedroom Sea Breeze Villa is located near The Ernest Hemingway Home and Museum, at 750 metres from the secluded pocket Dog Beach. The property features a fully equipped kitchen with a microwave… More

From US$ 414 Book Now

Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo

915 Eisenhower Drive, Key West, United States View map

Welcome to Eleuthera - 2X2 Fully Updated Old Town Waterfront Corner Condo, where plush sophistication meets laid-back comfort in the heart of Key West. This exquisite two-bedroom condo boasts… More

From US$ 184 Book Now

The Barbados -Bright Condo W Pool

Seaside Drive 3625, Key West, United States View map

The 2-bedroom Margarita Suite 305 is located at a 4.9 km distance from The Ernest Hemingway Home and Museum and within 10 minutes' drive of the historic fort "West Martello Tower". A kitchen with a… More

From US$ 282 Book Now

The Exuma Cay -Pool View & Parking

Seaside Drive 3625, Key West, United States View map

The 2-bedroom Grand Cayman Suite 309 offers accommodation in Key West, within 4.9 km of The Ernest Hemingway Home and Museum and within 25 minutes' walk of Smathers Beach. The villa also comes with a… More

From US$ 579 Book Now

Pescado Penthouse On Duval

Key West, United States View map

Pescado Penthouse On Duval Villa is located within 400 metres of The Ernest Hemingway Home and Museum and 10 minutes' drive to Key West International airport. The property features a kitchenette with… More

From US$ 191 Book Now

The Trinidad -Pool & Parking

Seaside Drive 3625, Key West, United States View map

Southernmost Point is within 4.8 km of the 2-bedroom Trinidad Suite 105 and Key West International airport is 5 minutes' drive away. The accommodation features a kitchen with a coffeemaker, a… More

From US$ 336 Book Now

Beachfront 2Bdr Condo Pool Hot Tub W Ocean Views Papaya Place By Avantstay

110A 1800 Atlantic Blvd, Key West, United States View map

The 0-bedroom Beachfront 2Bdr Condo Pool Hot Tub W Ocean Views Papaya Place By Avantstay Key West villa is situated around 400 metres from The Key West Nature Preserve and offers guests to relax with… More

From US$ 556 Book Now

Southernmost Sanctuary

1330 Simonton Street, Key West, United States View map

Southernmost Sanctuary Villa is situated about 15 minutes on foot from the vintage parish "Saint Paul's Episcopal Church of Key West" and within a 5-minute walk of Southernmost Point. While staying… More

From US$ 118 Book Now

The Andros -4Th Floor Sunset View

Seaside Drive 3625, Key West, United States View map

The 2-bedroom Great Exuma Suite 406 is located at a 3.5 km distance from Edward B. Knight Pier and 5 minutes' drive to Key West International airport. The accommodation has free parking and an… More

From US$ 491 Book Now

Conch Casa

Key West, United States View map

The Ernest Hemingway Home and Museum is situated 5 minutes on foot from the 2-bedroom Conch Casa Villa. Set close to Duval Street, the property is within close distance of Key West Aquarium. More

From US$ 614 Book Now

Aruba - Downtown Waterfront 2X2 Dock & Pool Pet-Friendly

915 Eisenhower Drive, Key West, United States View map

**Welcome to Aruba - Downtown Waterfront 2X2 Dock & Pool, a serene retreat immersed in the vibrant spirit of Key West.** Situated just 5 km from Key West International Airport, this pet-friendly… More

From US$ 789 Book Now

St Croix - Downtown 4X4 Waterfront Penthouse Pool Dock Pet

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St Croix - Downtown 4X4 Waterfront Penthouse Pool Dock Pet Villa Key West is located only 6 minutes' walk from the C. B. Harvey Rest Beach Park and offers guests to relish a patio as… More

From US$ 2229 Book Now

Just Steps To Duval- Sleeps 10- Heated Pool House

Truman Avenue 417, Key West, United States View map

Set in the vibrant heart of Duval, the Just Steps To Duval- Sleeps 10- Heated Pool House offers a unique retreat blending casual elegance with island-inspired charm. This exquisite villa is renowned… More

From US$ 1183 Book Now

Atlantic Paradise By Avantstay Great Location W Balcony Outdoor Dining Shared Pool Hot Tub

1800 Atlantic 108A, Key West, United States View map

This 1-bedroom villa is located merely 0.9 km from C. B. Harvey Rest Beach Park and 0.5 km from Key West International airport. The property features a fully equipped kitchen with coffee and tea… More

From US$ 1367 Book Now

New The Cottage At James House

512 Caroline Street, Key West, United States View map

Situated in the vibrant heart of Duval, New The Cottage At James House offers an inviting retreat, merging chic decor with a warm ambiance. This exquisite accommodation showcases stylish leather… More

From US$ 519 Book Now

Palm Gardens

905 White St, Key West, United States View map

Set just 1.1 km from The Ernest Hemingway Home and Museum and 15 minutes' walk from Higgs Beach Dog Park, Palm Gardens Villa is located in Key West. This Key West villa has a separate toilet, a bath… More

From US$ 123 Book Now

St Kitts - Downtown Waterfront Penthouse Pool Dock Parking

915 Eisenhower Drive, Key West, United States View map

Located around 5 minutes' walk from the Bayview Park, the 4-bedroom St Kitts - Downtown Waterfront Penthouse Pool Dock Parking Villa Key West offers quick access to various city attractions in the… More

From US$ 547 Book Now

Crawl To Duval W/ Hot Tub

415 Truman Avenue, Key West, United States View map

Crawl To Duval W/ Hot Tub Villa is an 8-minute stroll from the even Southernmost Point, and within 8 minutes' stroll of Southernmost Point of the Continental US Monument. The 1-bedroom villa… More

From US$ 1210 Book Now

Lavender Jungle By Avantstay Great Location W Patio Shared Pool Month-Long Stays

104 Southard Street #1, Key West, United States View map

Situated a 6-minute walk from Jackson Square, Lavender Jungle By Avantstay Great Location W Patio Shared Pool Month-Long Stays Key West villa entices guests with views of the pool. More

From US$ 425 Book Now

Paradise Place By Avantstay Key West Old Town Condo W Shared Pool

905 White St #1, Key West, United States View map

The 1-bedroom Paradise Place By Avantstay Key West Old Town Condo W Shared Pool is located 15 minutes' walk from C. B. Harvey Rest Beach Park and offers quick access to the Minor Saint Mary Star of… More

From US$ 789 Book Now

Salvador'S Seclusion

1016 Howe St #4, Key West, United States View map

Offering a location merely a 14-minute walk from Mel Fisher Maritime Heritage Museum, the 1-bedroom Salvador'S Seclusion Villa Key West gives access to various tourist spots in the area. More

From US$ 258 Book Now

Baya House

606 Truman Ave, #13, Key West, United States View map

**Baya House: A Premiere Stay in Key West** Nestled in the vibrant heart of Downtown Key West, Baya House invites travelers to indulge in a blend of comfort and elegance. More

From US$ 321 Book Now

Casa Bonita - Duval Square

1075 Duval Street R1, Key West, United States View map

Casa Bonita - Duval Square Villa Key West offers proximity to such city sites as Southernmost Point of the Continental US, located only a 6-minute walk away. More

From US$ 951 Book Now

Poolside Breeze Retreat

1800 Atlantic Blvd Unit A103, Key West, United States View map

Situated nearly 5 minutes' walk from The Key West Nature Preserve, the spacious 2-bedroom Poolside Breeze Retreat Apartment Key West offers guests easy access to various tourist attractions nearby. More

From US$ 1026 Book Now

Casa Papa Del Mar

1800 Atlantic Blvd, Unit C438, Key West, United States View map

The 2-bedroom Casa Papa Del Mar Villa Key West is nestled nearly a 5-minute walk from The Key West Nature Preserve and entices guests with a Jacuzzi and a sauna. Featuring a swimming pool, this… More

From US$ 709 Book Now

Casita De Catherine By Avantstay 1 Block To Duval St W Hot Tub

427 B Catherine St, Key West, United States View map

The even Southernmost Point is set about a 5-minute stroll from the 1-bedroom Casita De Catherine By Avantstay 1 Block To Duval St W Hot Tub. Located off South Beach, this Key West villa is just near… More

From US$ 446 Book Now

Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool

607 Amelia St, Key West, United States View map

Set close to South Beach, the 2-bedroom Tropical Dreaming By Avantstay 4 Blks To Beach Private Pool is a mere 600 metres from Duval Street. Guests of this property can use a free car park, a patio… More

From US$ 2051 Book Now

Leaward Isle Island Retreat

1800 Atlantic Blvd, Unit A105, Key West, United States View map

Set in Key West, the 2-bedroom Leaward Isle Island Retreat Villa is 1.1 km from Higgs Beach. The accommodation also has an equipped kitchenette area with fridges, an oven and kitchenware. More

From US$ 480 Book Now

Key West Found By Avantstay Close To Shops W Patio Shared Pool Month Long Stays Only

101 Front St #13, Key West, United States View map

Located only a 5-minute walk from the Mel Fisher Maritime Heritage Museum, the welcoming Key West Found By Avantstay Close To Shops W Patio Shared Pool Month Long Stays Only villa offers a swimming… More

From US$ 544 Book Now

High Tide In Key West

1800 Atlantic Blvd #B117, Key West, United States View map

Offering an outdoor swimming pool, the 138 m² High Tide In Key West Apartment is located only a 5-minute walk from The Key West Nature Preserve. This 2-bedroom apartment with a sauna is a short way… More

From US$ 522 Book Now

St Thomas - Waterfront Penthouse Sleeps 16 W Pool & Boat Dock

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St Thomas - Waterfront Penthouse Sleeps 16 W Pool & Boat Dock Villa Key West provides easy access to various city attractions, such as the Historic Charter Boat Row, situated a mere 6… More

From US$ 1741 Book Now

Curacao - Large 2X2 Waterfront Condo Great View Pool & Dock

915 Eisenhower Drive, Key West, United States View map

Nestled in the heart of a vibrant coastal paradise, the Curacao - Large 2X2 Waterfront Condo boasts breathtaking views that immediately capture your attention. Just 5 km from Key West International… More

From US$ 766 Book Now

Bahama House

522 Bahama Street Key West Historic District, Key West, United States View map

Situated in Key West, within 350 metres of Southernmost Point, the 3-bedroom Bahama House Villa provides accommodation with free self parking, an outdoor swimming pool and a picnic area. This Key… More

From US$ 2223 Book Now

Pool 2 Blocks To Duval St Gated Community Month Long Stays Shipyard Treasure By Avantstay

208-5 Southard St, Key West, United States View map

Offering pool views, the 0-bedroom Pool 2 Blocks To Duval St Gated Community Month Long Stays Shipyard Treasure By Avantstay Key West villa is situated a mere 5 minutes' walk from the Ernest… More

From US$ 438 Book Now

Duval Corner

Amelia Street 422, Key West, United States View map

The 1-bedroom Duval Corner Villa is situated in the centre of Key West only 1.5 km from Mallory Square. Located in the Duval district, this property provides guests with a fully equipped kitchen with… More

From US$ 676 Book Now

The Salt Cay -Modern & Pet Friendly

Seaside Drive 3625, Key West, United States View map

The 2-bedroom Salt Cay Suite 410 is situated in Key West, about 10 minutes by car from Duval Street and within a 15-minute drive of the waterfront Mallory Square. The accommodation also has a full… More

From US$ 992 Book Now

Bahama Gardens - Conch House

710 Thomas Street, Key West, United States View map

Bahama Gardens - Conch House Villa is situated in Key West, within a 5-minute walk of The Ernest Hemingway Home and Museum and 1.1 km from Simonton Street. The 2-bedroom villa also comes with a fully… More

From US$ 599 Book Now

Andros - Spacious 2X2 Waterfront Condo

Eisenhower Drive 915, Key West, United States View map

Situated approximately a 25-minute walk from the Southernmost Point of the Continental US, the 2-bedroom Andros - Spacious 2X2 Waterfront Condo Key West villa invites guests to relax at a patio. More

From US$ 876 Book Now

Nautical Adventures In Paradise

1800 Atlantic Blvd #C126, Key West, United States View map

**Nautical Adventures in Paradise Key West** Connected to the vibrant pulse of Key West, Nautical Adventures In Paradise is ideally situated just 2.5 km from the historic Southernmost Point and only… More

From US$ 545 Book Now

Tropical Paradise Key West

1800 Atlantic Blvd Unit A113, Key West, United States View map

Located nearly a 25-minute walk from Southernmost Point of the Continental US, the 2-room Tropical Paradise Key West Apartment is at a distance of 2.9 km from a top family-friendly place like Key… More

From US$ 506 Book Now

Rooftop Penthouse

623 Duval Street Penthouse Suite, Key West, United States View map

Situated just a 13-minute walk from the natural history museum "Florida Keys Eco-Discovery Center", the 1-bedroom Rooftop Penthouse Key West villa provides access to numerous tourist attractions in… More

From US$ 1123 Book Now

Tom'S Chicken Coop Key West

1800 Atlantic Blvd Unit A403, Key West, United States View map

Situated only 650 metres from Higgs Beach Dog Park, the 2-bedroom Tom'S Chicken Coop Key West Villa provides guests with a hot tub and a sauna for additional relaxation. Featuring a swimming pool… More

From US$ 598 Book Now

Paradise Found Cayo Hueso

1800 Atlantic Blvd Unit A111, Key West, United States View map

Featuring a swimming pool, the spacious Paradise Found Cayo Hueso Apartment is a 5-minute walk from The Key West Nature Preserve. Staying in this apartment, nestled within close proximity of Higgs… More

From US$ 597 Book Now

Duval Sea Turtle By Avantstay Great Location Close To Shops Shared Pool

1075-29 Duval Square, Key West, United States View map

This 2-bathroom villa is at 300 metres from The Ernest Hemingway Home and Museum and walking distance from the even Southernmost Point. The Key West villa also features a kitchen and amenities such… More

From US$ 551 Book Now

Mermaids Retreat At Coral Hammock

41 Coral Way, Key West, United States View map

Situated just 6 minutes' walk from FYT Fitness Center, the 3-bedroom Mermaids Retreat At Coral Hammock Key West villa offers easy access to numerous tourist spots in the area. More

From US$ 713 Book Now

Sandpiper On The Ocean

1800 Atlantic Blvd C420, Key West, United States View map

To enjoy your vacation in Key West, stay at the 2-room Sandpiper On The Ocean Apartment Key West, which is within a 3-km distance of Fort Zachary Taylor and around a 25-minute stroll from Key West… More

From US$ 695 Book Now