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2026-06-28
2026-06-29
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Key West holiday rentals

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

Seaside Drive 3625, Key West, United States View map

The 2-bedroom Tortuga Suite At Sunrise Suites Resort - Heated Pool, Hot Tub & Free Parking Key West villa is located just 0.8 km from Thompson Island and allows guests to enjoy cycling and fishing. 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

Sea Breeze -Great Location!

Whitehead Street 1025, Key West, United States View map

Up to 6 guests can stay at the 2-bedroom Sea Breeze -Great Location! Villa Key West and enjoy the Key West Lighthouse and Keeper's Quarters Museum, located about a 5-minute walk away. The holiday… More

From US$ 536 Book Now

Amelia House

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

Amelia House Villa Key West offers quick access to such city attractions as the South Beach, located nearly a 5-minute walk away. More

From US$ 270 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

The Barbados -Bright Condo W Pool

Seaside Drive 3625, Key West, United States View map

Located merely 0.8 km from Thompson Island, The Barbados -Bright Condo W Pool Key West villa provides access to various tourist attractions in the vicinity. More

From US$ 282 Book Now

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

Duval Street 1075, Key West, United States View map

Up to 6 guests can stay at the 2-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool Key West and enjoy the Key West Lighthouse and Keeper's Quarters Museum, located approximately a 5… More

From US$ 343 Book Now

The Exuma Cay -Pool View & Parking

Seaside Drive 3625, Key West, United States View map

Offering a location 4.8 km from Southernmost Point of the Continental US Monument, The Exuma Cay -Pool View & Parking Villa Key West gives access to various tourist spots in the area. More

From US$ 579 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$ 512 Book Now

Southernmost Sanctuary

1330 Simonton Street, Key West, United States View map

Located 850 metres from the historical Key West Lighthouse, Southernmost Sanctuary Villa Key West provides access to various tourist attractions in the vicinity. More

From US$ 118 Book Now

The Andros -4Th Floor Sunset View

Seaside Drive 3625, Key West, United States View map

Offering a location approximately a 25-minute walk from Sheriff s Animal Farm, The Andros -4Th Floor Sunset View Villa Key West gives access to various tourist spots in the area. More

From US$ 491 Book Now

The Trinidad -Pool & Parking

Seaside Drive 3625, Key West, United States View map

The Trinidad -Pool & Parking Villa Key West offers proximity to nearby tourist spots, such as the Key West Golf Club, situated approximately 25 minutes' walk away. Guests can enjoy cycling and… More

From US$ 336 Book Now

Kw24 Key Lime Calypso

409 Petronia Ave, Key West, United States View map

Situated 15 minutes' stroll from the waterfront Mallory Square, Key Lime Calypso Villa Key West provides access to numerous tourist attractions in the area. More

From US$ 333 Book Now

Kw44 Conch Casa

Key West, United States View map

Conch Casa Villa Key West is nestled merely 1.2 km from the Key West Aquarium and provides a Jacuzzi. More

From US$ 614 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 situated approximately 5 minutes' walk from the Wreckers Sloop Mary, featuring such comforts as high-speed… More

From US$ 1966 Book Now

Papaya Place By Avantstay

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

Located within a 3-km distance of the fully accredited Mel Fisher Maritime Heritage Museum, the 0-bedroom Papaya Place By Avantstay Key West villa features a swimming pool, a hot tub, ensuring a… More

From US$ 556 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

Great Key West Location

100 Admirals Lane, Key West, United States View map

Great Key West Location Villa offers swift access to various city sites, such as the fully accredited Mel Fisher Maritime Heritage Museum, situated merely 7 minutes' walk away. More

Book Now

Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-Friendly

915 Eisenhower Drive, Key West, United States View map

Offering a patio overlooking the sea, the 2-bedroom Key West Downtown Waterfront, Sleeps 8, Dock & Pool Pet-Friendly Villa is located about a 5-minute walk from the Bayview Park. Providing guests… More

From US$ 1144 Book Now

Frost Free In Cayo Hueso

1800 Atlantic Blvd Unit C439, Key West, United States View map

Located just a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Frost Free In Cayo Hueso Villa is suitable for 6 guests and provides a swimming pool to relax in. The holiday home features… More

From US$ 674 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

Lavender Jungle By Avantstay

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

Lavender Jungle By Avantstay Key West villa offers proximity to nearby tourist spots, such as the Harry S. Truman Little White House, situated 8 minutes' walk away. Located just 1.7 km from the Key… More

From US$ 425 Book Now

Crawl To Duval W/ Hot Tub

415 Truman Avenue, Key West, United States View map

Offering a Jacuzzi, Crawl To Duval W/ Hot Tub Villa Key West is situated just 150 m from the Higgs Beach Dog Park and can accommodate 6 people. Featuring free private parking on site, this 2-bedroom… More

From US$ 1642 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$ 1144 Book Now

St Kitts - Downtown Waterfront Penthouse Pool Dock Parking

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St Kitts - Downtown Waterfront Penthouse Pool Dock Parking Villa Key West is located approximately 20 minutes' walk from the Ernest Hemingway Home and Museum and provides cycling and… More

From US$ 547 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 the historical Key West Lighthouse, located just a 5-minute walk away. More

From US$ 951 Book Now

Latitude Penthouse Key West

1800 Atlantic Blvd Unit B417, Key West, United States View map

Featuring a Jacuzzi and a sauna, the 2-bedroom Latitude Penthouse Key West Villa is located only a 9-minute walk from the Higgs Beach Dog Park and can host up to 6 guests. The holiday home features… More

From US$ 685 Book Now

Salvador'S Seclusion

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

The 1-bedroom Salvador'S Seclusion Villa Key West is nestled just a 6-minute walk from Southernmost Point of the Continental US Monument and can accommodate up to 2 guests. This 1-bathroom villa… More

From US$ 258 Book Now

Key West Found By Avantstay

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

The welcoming Key West Found By Avantstay villa is located 18 minutes' walk from the very unusual Key West Cemetery and invites guests to enjoy a patio. More

From US$ 544 Book Now

Casita De Catherine By Avantstay

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

Located around 5 minutes' walk from the Key West Butterfly and Nature Conservatory, the 0-bedroom Casita De Catherine By Avantstay 1 Block To Duval St W Hot Tub Key West villa offers quick access to… More

From US$ 446 Book Now

Key West'S Best

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

Located just a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Key West'S Best villa invites guests to enjoy a Jacuzzi and a sauna. The holiday home features opportunities for snorkelling… More

From US$ 644 Book Now

Poolside Breeze Retreat

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

Situated merely 1.6 km from the Higgs Beach, the 2-bedroom Poolside Breeze Retreat Villa Key West boasts a sauna, as well as a spa salon for guests to relax in. Located about a 10-minute ride from… More

From US$ 1026 Book Now

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

915 Eisenhower Drive, Key West, United States View map

Situated around a 10-minute walk from the Key West Firehouse Museum, the 4-bedroom St Thomas - Waterfront Penthouse Sleeps 16 W Pool & Boat Dock Villa Key West invites guests to relax at a patio. More

From US$ 1741 Book Now

High Tide In Key West

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

Situated merely a 9-minute walk from the Higgs Beach Dog Park, High Tide In Key West Villa offers a sauna and can accommodate up to 6 guests. The 2-bedroom holiday home features opportunities for… More

From US$ 522 Book Now

Duval Street Suite Overlooking Duval With Parking And Pool

824 Duval Street, Key West, United States View map

The 1-bedroom Duval Street Suite Overlooking Duval With Parking And Pool Key West villa is nestled about 5 minutes' walk from the downtown commercial zoned Duval Street and can accommodate up to 4… More

From US$ 763 Book Now

Coral Hammock Poolside Home

28 Coral Way, Key West, United States View map

Located within 600 metres of Key West Baptist Temple, Coral Hammock Poolside Home Key West has a heated swimming pool and is ideal for up to 8 guests. Guests can enjoy windsurfing, snorkelling, and… More

From US$ 463 Book Now

Kw42 Bahama House

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

Situated in the Downtown Key West district, a mere 1.9 km from the Fort Zachary Taylor, Bahama House Villa Key West comes with a swimming pool for guests to unwind. Guests can enjoy cycling and… More

From US$ 1360 Book Now

Sandpiper On The Ocean

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

Located merely 9 minutes' stroll from the Higgs Beach Dog Park, the 2-bedroom Sandpiper On The Ocean Key West villa comes with an outdoor swimming pool, a Jacuzzi and a sauna. Located 2.7 km from the… More

From US$ 613 Book Now

Sweet Caroline

Caroline Street 537, Key West, United States View map

Sweet Caroline Villa Key West, situated right in the centre of Key West, and an 8-minute walk from the bustling plaza "Mallory Square", can accommodate up to 8 guests. Located a short way from the… More

From US$ 864 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, located nearly a 5-minute walk from The Key West Nature Preserve, entices guests with a swimming pool as well as a Jacuzzi and a sauna to relax in. At… More

From US$ 709 Book Now

La Brisa Unit 105 North Building

South Roosevelt Boulevard 1901, Key West, United States View map

Featuring an outdoor swimming pool, La Brisa Unit 105 North Building Villa Key West is suitable for up to 6 people and is located 2.5 km from the Ernest Hemingway Home and Museum. Providing guests… More

From US$ 741 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 Salt Cay -Modern & Pet Friendly

Seaside Drive 3625, Key West, United States View map

The Salt Cay -Modern & Pet Friendly Villa Key West offers proximity to nearby tourist spots, such as Thompson Island, situated just an 11-minute walk away. More

From US$ 992 Book Now

Duval Corner

Amelia Street 422, Key West, United States View map

Duval Corner Villa Key West offers proximity to such city sites as the even Southernmost Point, located merely 6 minutes' walk away. More

From US$ 676 Book Now

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

Moonlight Paradise

1800 Atlantic Blvd C224, Key West, United States View map

Located only a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Moonlight Paradise Key West villa features an outdoor swimming pool and can accommodate up to 6 guests. Offering a sauna, the… More

From US$ 709 Book Now

Botanical Island Delight

1800 Atlantic Blvd, #C120, Key West, United States View map

Featuring an outdoor swimming pool, the 2-bedroom Botanical Island Delight Villa Key West is located only 5 minutes' walk from The Key West Nature Preserve and is suitable for up to 4 guests. More

From US$ 455 Book Now

Andros - Spacious 2X2 Waterfront Condo

Eisenhower Drive 915, Key West, United States View map

Offering a patio overlooking the sea, the 2-bedroom Andros - Spacious 2X2 Waterfront Condo Key West villa is located only 5 minutes' walk from the Wreckers Sloop Mary. Providing guests with high… More

From US$ 876 Book Now

Bahama Gardens - Conch House

710 Thomas Street, Key West, United States View map

Bahama Gardens - Conch House Villa Key West is located only a 5-minute walk from the Ernest Hemingway Home and Museum and offers a hot tub, ensuring guests a relaxing stay. Situated in the Downtown… More

From US$ 599 Book Now