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2026-11-13
2026-11-14
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Private Villas in Key West

Absolutely Paradise

1011 Simonton Street #3, Key West, United States View map

During the stay at Absolutely Paradise Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Fort Zachary Taylor, located 20 minutes' walk away. Situated in the… More

From US$ 1973 Book Now

Octopus Garden By Last Key Realty

55 Coral Way, Key West, United States View map

Octopus Garden By Last Key Realty Key West villa is located 18 minutes' walk from Safe Harbor and provides a heated swimming pool, ensuring a relaxing stay. More

From US$ 615 Book Now

Namaste

219 Ann Street Rear, Key West, United States View map

Situated about a 25-minute walk from the White Street Pier, the 1-bedroom Namaste Villa Key West invites guests to relax at a patio. This 2-bathroom villa is located in Duval with unique, island… More

From US$ 835 Book Now

Prime Downtown Location - Truman Little Cozy Cottage

910 Simonton Street 3, Key West, United States View map

Up to 2 guests can stay at Prime Downtown Location - Truman Little Cozy Cottage Key West and enjoy Saint Mary Star of the Sea Basilica, located 6 minutes' walk away. More

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Island Pearls

527 Fleming Street, Key West, United States View map

The 2-bedroom Island Pearls Villa Key West entices guests to enjoy windsurfing, snorkelling, and fishing and offers proximity to the Vandenberg Wreck, located just 5 minutes' stroll away. The Key… More

From US$ 1551 Book Now

Keys Please!

Louisa Street 514, Key West, United States View map

The 3-bedroom Keys Please! Villa Key West is located about a 20-minute walk from the White Street Pier and provides cycling and fishing for active guests. Situated in Duval with unique, island… More

From US$ 1910 Book Now

Mastway House -Pool & Dock!

Key Haven Terrace 4, Key West, United States View map

The 4-bedroom Mastway House -Pool & Dock! Villa Key West entices active guests with access to a fitness room and is located 3.8 km from Sigsbee Park Island. Featuring a patio, this holiday home is… More

From US$ 3115 Book Now

Sweet Home Angelita By Last Key Realty

421 Angela Street, Key West, United States View map

Sweet Home Angelita By Last Key Realty Key West, located a 6-minute walk from the historic Key West Lighthouse, can host up to 13 guests. More

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Atlantic Parrot

1800 Atlantic Boulevard #435C, Key West, United States View map

Located within 600 metres of the White Street Pier, Atlantic Parrot Villa Key West is suitable for 5 guests and provides an outdoor swimming pool to relax in. More

From US$ 554 Book Now

Kwss202 Sunrise Suites - Big Kahuna Suite 202

3625 Seaside Dr #202, Key West, United States View map

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Conch Adventure By Avantstay

104 Southard Street #3, Key West, United States View map

Situated merely a 6-minute walk from Mile Marker 0 Store, the 0-bedroom Conch Adventure By Avantstay Key West villa offers easy access to numerous tourist spots in the area. Located 2.1 km from The… More

From US$ 369 Book Now

Royal Palm Suite At Travelers Palm Inn Key West

815 Catherine St., Key West, United States View map

Offering a swimming pool, the 1-bedroom Royal Palm Suite At Travelers Palm Inn Key West villa is located merely 9 minutes' walk from the Key West Butterfly and Nature Conservatory and is ideal for up… More

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Coastal Comfort

2851 Key Cove Dr., Key West, United States View map

Coastal Comfort Key West villa offers proximity to such city sites as the Kelly's Aerial Arts & Fitness, located just 6 minutes' walk away. Staying at the property, which is around 3 km from the… More

From US$ 1745 Book Now

First Breath By Avantstay

1106 Eaton Street, Key West, United States View map

Situated a 6-minute walk from the Papa's Pilar Rum Distillery, the welcoming First Breath By Avantstay Key West villa entices guests with views of the pool. More

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Bootlegger Bay @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Situated nearly 5 minutes' walk from the comfortable Bootlegger Bay @ Speakeasy Inn Key West!, guests can reach the Key West Butterfly and Nature Conservatory in no time. This Key West guest house… More

From US$ 570 Book Now

Key West Charming By Avantstay

210-7 Southard St, Key West, United States View map

The 0-bedroom Key West Charming: Poolside Retreat Near Fort Zachary Taylor villa offers proximity to such city sites as the San Carlos Institute, located merely a 7-minute walk away. More

From US$ 396 Book Now

Heron Suite | Vibrant Retreat, Hot Tubs, Steps From Duval

1330 Simonton Street #2, Key West, United States View map

Staying at the 1-bedroom Heron Suite | Vibrant Retreat, Hot Tubs, Steps From Duval Key West villa, guests can visit the downtown commercial zoned Duval Street, which is only 1 km away. Offering a… More

From US$ 219 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

New The Windrose House - Pool & Pets

Shoreline Road 3, Key West, United States View map

The 6-bedroom New The Windrose House - Pool & Pets Villa Key West is located around 20 minutes' walk from Safe Harbor and provides a private pool, ensuring a relaxing stay. The holiday home hosts up… More

From US$ 2971 Book Now

Duval Hideaway

1124 Duval Street B, Key West, United States View map

**Discover the Duval Hideaway Villa in the Heart of Key West** Conveniently located, the villa is within walking distance to the bustling nightlife and unique shops that Duval Street is renowned for. More

From US$ 515 Book Now

Mar Y Sol Ocean Front

1800 Atlantic Blvd #101, Key West, United States View map

Mar Y Sol Ocean Front Villa Key West is located 25 minutes' walk from the downtown commercial zoned Duval Street and invites guests to join windsurfing, snorkelling, and fishing. Featuring a sauna… More

From US$ 871 Book Now

Belle Of The Beach By Last Key Realty

1815 Atlantic Boulevard, Key West, United States View map

Situated only 8 minutes' walk from the Higgs Beach Dog Park, Belle Of The Beach By Last Key Realty Key West villa is ideal for up to 16 guests. More

From US$ 2288 Book Now

Kingfish Keep

1201 Duval Street 3, Key West, United States View map

Situated just a 5-minute walk from Southernmost Point of the Continental US Monument, Kingfish Keep Villa Key West is ideal for up to 4 guests. More

From US$ 421 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

Petes Cottages

505-507 Louisa Street, Key West, United States View map

During the stay at Petes Cottages Key West, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Harry S. Truman Little White House, located a 15-minute walk away. The 4-bedroom… More

From US$ 937 Book Now

Villa The Watson House

525 Simonton Street, Key West, United States View map

The 4-bedroom Villa The Watson House Key West accommodates up to 8 guests and offers proximity to the Vandenberg Wreck, located merely a 5-minute walk away. The property features opportunities for… More

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Atlantic Sunrise Penthouse

1800 Atlantic Blvd, Unit C425, Key West, United States View map

The 3-bedroom Atlantic Sunrise Penthouse Villa Key West hosts up to 8 guests and provides proximity to the Higgs Beach Dog Park, situated only a 9-minute walk away. Featuring a Jacuzzi and a sauna… More

From US$ 941 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$ 753 Book Now

Tom'S Oceanfront Penthouse

1800 Atlantic Blvd Unit A401, Key West, United States View map

Located approximately a 25-minute walk from the downtown commercial zoned Duval Street, the 3-bedroom Tom'S Oceanfront Penthouse Villa Key West has an outdoor swimming pool and is ideal for up to 8… More

From US$ 1057 Book Now

Tropical Dreaming By Avantstay

607 Amelia St, Key West, United States View map

Nestled only a 12-minute walk from the San Carlos Institute, the welcoming Tropical Dreaming By Avantstay Key West villa features a swimming pool along with a patio to help guests unwind. Boasting… More

From US$ 2051 Book Now

Petes West Cottage

505 Louisa Street, Key West, United States View map

Featuring a heated swimming pool, the 2-bedroom Petes West Cottage Key West is located only a 6-minute walk from the even Southernmost Point and is suitable for up to 4 guests. This holiday home… More

From US$ 928 Book Now

Good Vibrations By Last Key Realty

524 Dupont Lane, Key West, United States View map

Situated only a few steps from the Key West Lighthouse and Keeper's Quarters Museum, Good Vibrations By Last Key Realty Key West villa offers easy access to numerous tourist spots in the area. More

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Casa De Cubana

512 Amelia Street, Key West, United States View map

The 2-bedroom Casa De Cubana Villa Key West accommodates up to 4 guests and offers proximity to the Key West Butterfly and Nature Conservatory, located only a 7-minute walk away. More

From US$ 2269 Book Now

Amelia Home By Avantstay

605 Amelia Street, Key West, United States View map

Located around 10 minutes' walk from the downtown commercial zoned Duval Street, the 0-bedroom Amelia Home By Avantstay Key West boasts a swimming pool with a patio for additional relaxation. More

From US$ 903 Book Now

Jasmine Place

919 Whitehead Street, Key West, United States View map

During the stay at Jasmine Place Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the 19 - acre Key West Cemetery, located a 13-minute walk away. More

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Hideaway @ Speakeasy Inn Key West!

1117 Duval St., Key West, United States View map

Located only 400 metres from the South Beach, the comfortable Hideaway @ Speakeasy Inn Key West! offers Wi-Fi in the rooms and a car park. This Key West guest house lies in the Downtown Key West… More

From US$ 467 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$ 696 Book Now

Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval!

1330 Simonton Street #1, Key West, United States View map

The 1-bedroom Egret Suite | Bright Retreat, Hot Tubs, Steps From Duval! Key West villa hosts up to 4 guests and provides proximity to the Key West Butterfly and Nature Conservatory, situated… More

From US$ 354 Book Now

Renovated Corner Unit

620 Thomas Unit 150, Key West, United States View map

Situated approximately a 5-minute walk from the Alan S Maltz Gallery, the 2-bedroom Renovated Corner Unit Villa Key West entices guests to explore various tourist attractions in the area. More

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New The Altair House - Fire Pit Pool & Hot Tub

Mangrove Lane 13, Key West, United States View map

Featuring a private pool, the 6-bedroom New The Altair House - Fire Pit Pool & Hot Tub Villa Key West is suitable for up to 14 people and is located about a 15-minute walk from the Key West Tropical… More

From US$ 4188 Book Now

Ibis By Avantstay

714 Olivia #11, Key West, United States View map

Staying at the 0-bedroom Ibis By Avantstay Key West villa, guests can visit Mile Marker 0 Store, which is only 1 km away. More

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Oceanfront Oasis

1901 South Roosevelt Blvd, Unit 304, Key West, United States View map

The 2-bedroom Oceanfront Oasis Villa Key West entices guests to enjoy windsurfing, snorkelling, and canoeing and offers proximity to the Higgs Beach Dog Park, located approximately a 5-minute stroll… More

From US$ 550 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

Catherine House

518 Catherine Street, Key West, United States View map

During the stay at Catherine House Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Key West Aquarium, located a 16-minute walk away. Offering a private… More

From US$ 759 Book Now

Anchor Drop Key West

1800 Atlantic Blvd, Unit A307, Key West, United States View map

During the stay at Anchor Drop Key West Villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Higgs Beach, located a 19-minute walk away. The 2-bedroom holiday home offers… More

From US$ 870 Book Now

Smooth Sailing By Last Key Realty

1800 Atlantic Blvd #C334, Key West, United States View map

Offering a Jacuzzi, Smooth Sailing By Last Key Realty Key West villa is situated merely a 7-minute walk from the fully accredited Mel Fisher Maritime Heritage Museum and can accommodate 6 people. More

From US$ 1034 Book Now

Pilars Secret

716 Duval St Rear, Key West, United States View map

During the stay at Pilars Secret Villa Key West, guests can indulge in windsurfing, snorkelling, and canoeing or visit the natural history museum "Florida Keys Eco-Discovery Center", located a 13… More

From US$ 1217 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

Andros Suite

921 Center Street #6, Key West, United States View map

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Casita Angelita By Last Key Realty

421 Angela Street Unit A, Key West, United States View map

Casita Angelita By Last Key Realty Key West villa accommodates up to 6 guests and offers proximity to the downtown commercial zoned Duval Street, located merely a 7-minute walk away. More

From US$ 750 Book Now