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2026-02-05
2026-02-06
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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

Amelia House

Key West Florida 33040, Key West, United States View map

The 3-bedroom Amelia House Villa is located near the downtown commercial zoned Duval Street, at a 1.2 km distance from the fully accredited Mel Fisher Maritime Heritage Museum. The property also has… More

From US$ 270 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

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

New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool

Duval Street 1075, Key West, United States View map

Situated in the Duval district, the 3-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool right next to Key West Butterfly and Nature Conservatory and nearly 20 minutes' walk from the… More

From US$ 343 Book Now

Truman

Key West, United States View map

Truman Key West is an idyllic retreat that captures the essence of laid-back island living. Nestled in the heart of Duval, this charming studio destination is only a short stroll from the vibrant… More

From US$ 227 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

Hemingway'S View

Key West, United States View map

The 3-bedroom Hemingway'S View Villa is located near The Ernest Hemingway Home and Museum, only 0.6 km from Southernmost Point. The property features a kitchen with a microwave, coffee/tea making… More

From US$ 1175 Book Now

Windward Isle

531 Olivia St, Key West, United States View map

Only 10 minutes' walk from the Harry S. Truman Little White House, Windward Isle Villa is just off The Ernest Hemingway Home and Museum. This villa comprises 2 bedrooms and 1 bathroom. More

From US$ 312 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 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

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

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

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

Experience the vibrant allure of Key West at Papaya Place by Avantstay, a captivating retreat just 5 km from Key West International Airport. This hidden gem boasts an enviable location that… More

From US$ 556 Book Now

Key Lime Calypso

409 Petronia Ave, Key West, United States View map

Key Lime Calypso Villa is situated in Key West, within a 5-minute walk of the downtown commercial zoned Duval Street and 15 minutes on foot from the secluded pocket Dog Beach. While staying at the 2… More

From US$ 333 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$ 1084 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

Sky Loft In Key West

Southard Street 611, Key West, United States View map

Positioned in the heart of Duval, the Sky Loft in Key West is an exquisite blend of laid-back luxury and sophisticated charm. This unique villa captures the essence of Key West while providing guests… More

From US$ 644 Book Now

Casa Key West-Pool & Free Parking

Duval Street 1075, Key West, United States View map

The 3-bedroom Casa Key West At Duval Square Villa in Key West is a mere 1.3 km from Higgs Beach. A fully furnished kitchen with a microwave, coffee/tea making facilities and fridges is included at… More

From US$ 1090 Book Now

Tradewinds

529 531 Olivia St, Key West, United States View map

Nestled in the vibrant heart of Duval, Tradewinds Villa Key West offers an idyllic retreat steeped in island charm. This enchanting property welcomes guests with its captivating design and a warm… More

From US$ 2805 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

Villa Positano -Rooftop Pool On Duval

Duval Street 1075, Key West, United States View map

Located in the Duval district with South Beach nearby, the 2-bedroom Sea Esta Suite lies a mere 300 metres from Southernmost Point. The accommodation also has a fully furnished kitchen with a… More

From US$ 762 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 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

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

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

Nestled in the vibrant heart of Key West, Lavender Jungle By Avantstay beckons travelers seeking an idyllic sanctuary. 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$ 611 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

Key West'S Best

1800 Atlantic Blvd, Unit C326, Key West, United States View map

The 2-bedroom Sunrise On Atlantic Villa offers accommodation in Key West, at a 2.1 km distance from the even Southernmost Point and 950 metres of C. B. Harvey Rest Beach Park. This villa in Key West… More

From US$ 644 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

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$ 1128 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 is situated about a 5-minute walk from Wreckers Sloop Mary, featuring such comforts as Wi-Fi and parking. 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$ 1218 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 welcoming Pool 2 Blocks To Duval St Gated Community Shipyard Treasure By Avantstay Key West villa is situated a mere 5 minutes' walk from the Ernest Hemingway Home and Museum. More

From US$ 438 Book Now

Curry House - Room 9

Fleming Street 806, Key West, United States View map

Nestled in the picturesque island of Key West, the Curry House offers a charming blend of tropical elegance and modern comfort. Just 10 km from the bustling Key West International Airport, this… More

From US$ 184 Book Now

The Samana Cay -Private Balcony

Seaside Drive 3625, Key West, United States View map

Fort East Martello Museum is within 10 minutes' walk of the 2-bedroom Samana Cay Suite 405, while The Ernest Hemingway Home and Museum is within 4.9 km of here. The Key West villa also offers free… More

From US$ 402 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

Casa Papa Del Mar

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

The 2-bedroom Casa Pap Del Mar Villa is located approximately 25 minutes on foot from the downtown commercial zoned Duval Street and offers quick access to Smathers Beach. The accommodation features… 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

Andros - Spacious 2X2 Waterfront Condo

Eisenhower Drive 915, Key West, United States View map

Situated nearly a 25-minute walk from Smathers Beach, the 2-bedroom Andros - Spacious 2X2 Waterfront Condo Key West villa invites guests to relax at a patio. Guests can enjoy cycling and fishing at… More

From US$ 876 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$ 656 Book Now

Duval Street Suite Overlooking Duval With Parking And Pool

824 Duval Street, Key West, United States View map

Located in the Duval district with The Ernest Hemingway Home and Museum nearby, the 1-bedroom Duval Street Suite Overlooking Duval With Parking And Pool lies a mere 10 minutes' stroll from South… More

From US$ 763 Book Now

Parrot Perch By Avantstay Old Town Key West W Shared Pool Month-Long Stays Only

620 Thomas St #249, Key West, United States View map

Situated in the Downtown Key West district, this 2-bedroom and 2-bathroom villa right next to The Ernest Hemingway Home and Museum and 15 minutes' walk from South Beach. It includes Wi-Fi throughout… More

From US$ 223 Book Now

Sweet Caroline

Caroline Street 537, Key West, United States View map

Sweet Caroline Villa offers accommodation just 400 metres from Simonton Beach, while Key West Aquarium is about a 5-minute stroll away. This villa is equipped with 2 bedrooms plus a kitchen with a… More

From US$ 932 Book Now

The Grand Turk -Sunset View & Pool

Seaside Drive 3625, Key West, United States View map

The 2-bedroom Grand Turk Suite 404 is 4.8 km from the even Southernmost Point, while Sheriff s Animal Farm is approximately 20 minutes' walk away. The Key West villa has a kitchen provided with… More

From US$ 295 Book Now