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2026-11-06
2026-11-07
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Holiday Homes in Key West

Runaway Bills

812 Johnson Lane, Key West, United States Show map

Offering an outdoor swimming pool, the 3-bedroom Runaway Bills Key West villa is situated only a 7-minute walk from the downtown commercial zoned Duval Street and can accommodate up to 6 guests. More

From US$ 297 Book Now

The Mellow Macaw By Last Key Realty

1025D Whitehead Street, Key West, United States Show map

Offering a swimming pool, The Mellow Macaw By Last Key Realty Key West villa is situated 0.6 km from the downtown commercial zoned Duval Street and can accommodate up to 6 guests. Located a 20-minute… More

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Kingfish Keep

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

The 1-bedroom Kingfish Keep Villa Key West offers proximity to such city sites as the even Southernmost Point, located only a 5-minute walk away. This Key West holiday home is suitable for up to 4… More

From US$ 421 Book Now

Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock

915 Eisenhower Drive, Key West, United States Show map

Featuring a swimming pool, the 2-bedroom Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock Key West villa is located about a 5-minute walk from Bayview Park and is suitable for up to 8 guests… More

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Fleming-O

726 Fleming St, Key West, United States Show map

Situated around 5 minutes' walk from Key West Historic Seaport, the 2-bedroom Fleming-O Villa Key West entices guests with windsurfing, snorkelling, and canyoning in the area. Providing guests with… More

From US$ 1018 Book Now

New The Windrose House - Pool & Pets

Shoreline Road 3, Key West, United States Show map

The 6-bedroom New The Windrose House - Pool & Pets Villa Key West is located about a 25-minute walk from the newly developed Stock Island Marina Village and welcomes its guests to enjoy fisheries. More

From US$ 2971 Book Now

Tranquility By The Beach

1800 Atlantic Blvd C129, Key West, United States Show map

Offering a swimming pool, the 2-bedroom Tranquility By The Beach Key West villa is located a mere 9 minutes' walk from Higgs Beach Dog Park and is ideal for up to 6 guests. Featuring a sauna, this… More

From US$ 760 Book Now

Duke Of Catherine By Last Key Realty

512 Catherine Street #2, Key West, United States Show map

Located just 550 metres from the downtown commercial zoned Duval Street, the 2-bedroom Duke Of Catherine By Last Key Realty Key West villa provides a swimming pool, a Jacuzzi for a more relaxing… More

From US$ 1203 Book Now

Sailboat Stay And Resort Amenities

7005 Shrimp Road, Key West, United States Show map

Sailboat Stay And Resort Amenities Key West villa is a 5-minute walk from the newly developed Stock Island Marina Village, which includes bicycles for rent. More

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Smooth Sailing By Last Key Realty

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

Situated only 5 minutes on foot from Higgs Beach Dog Park, the 2-bedroom Smooth Sailing By Last Key Realty Key West villa can host up to 6 guests and offers a Jacuzzi, ensuring a relaxing stay. More

From US$ 1034 Book Now

Atlantic Paradise Found

1800 Atlantic Blvd C232, Key West, United States Show map

The Key West Nature Preserve is 5 minutes' walk from Atlantic Paradise Found Key West villa, offering a sauna for guests' relaxation. Located 3.2 km from the bustling plaza "Mallory Square", the 2… More

From US$ 674 Book Now

The Southern Cross Tropical Village

1400 Alberta St #B, Key West, United States Show map

Offering a swimming pool, the 2-bedroom The Southern Cross Tropical Village Key West villa is located just 8 minutes' walk from Higgs Beach and is ideal for up to 6 guests. The property features… More

From US$ 576 Book Now

Barbuda Suite By Last Key Realty

329 William Street #4, Key West, United States Show map

Located 450 metres from Vandenberg Wreck, Barbuda Suite By Last Key Realty Key West villa features a swimming pool and can accommodate up to 4 guests. Situated in the Downtown Key West district, the… More

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Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom

915 Eisenhower Drive, Key West, United States Show map

Located only a 9-minute walk from Fleming Street, the 2-bedroom Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom Key West villa features a swimming pool and can accommodate up to 8… More

From US$ 776 Book Now

Ann Street Cottage

219 Ann Street #2, Key West, United States Show map

Featuring a heated pool, Ann Street Cottage Key West is suitable for up to 2 people and is located 20 minutes' walk from Key West Firehouse Museum. The 1-bedroom holiday home features opportunities… More

From US$ 711 Book Now

Louisa House

521 Louisa Street, Key West, United States Show map

Offering a swimming pool, the 4-bedroom Louisa House Villa Key West is situated just a 6-minute walk from Southernmost Point of the Continental US Monument and can accommodate up to 10 guests. This 1… More

From US$ 1399 Book Now

Charming Key West Rental

3 Coral Way, Key West, United States Show map

Featuring an outdoor swimming pool, Charming Key West Rental villa is located within a 200-metre distance of FYT Fitness Center and is suitable for up to 8 guests. Located 10 minutes' drive from Fort… More

From US$ 680 Book Now

The Crestwood House - Private Heated Pool & Parking

Shoreline Road 17, Key West, United States Show map

Located around a 25-minute walk from Key West Golf Club, the 6-bedroom The Crestwood House - Private Heated Pool & Parking Villa Key West has an outdoor swimming pool and is ideal for up to 14 guests… More

From US$ 2726 Book Now

Aquaria House -Pool & Boat Dock

Shoreline Road 14, Key West, United States Show map

Situated approximately 15 minutes' walk from Key West Tropical Forest and Botanical Garden, the 4-bedroom Aquaria House -Pool & Boat Dock Villa Key West provides fitness classes, as well as a fitness… More

From US$ 3784 Book Now

Duval Sea Turtle By Avantstay

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

Offering an outdoor swimming pool, the welcoming Duval Sea Turtle By Avantstay Key West villa is located only a 6-minute walk from Key West Butterfly and Nature Conservatory and is ideal for up to 6… More

From US$ 551 Book Now

Coastal Comfort

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

Coastal Comfort Key West villa is located about a 25-minute walk from Higgs Beach Dog Park and provides snorkelling, canyoning, and fisheries for active guests. Featuring a Jacuzzi, the holiday home… More

From US$ 1745 Book Now

Key West Charming By Avantstay

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

Offering an outdoor swimming pool, the welcoming Key West Charming: Poolside Retreat Near Fort Zachary Taylor villa is situated a mere 8 minutes' walk from The Ernest Hemingway Home and Museum and… More

From US$ 396 Book Now

Ibis Suite | Bright Hideaway, Hot Tubs, Steps From Duval!

1330 Simonton Street #3, Key West, United States Show map

Situated within 5 minutes' walk of the even Southernmost Point, the 1-bedroom Ibis Suite | Bright Hideaway, Hot Tubs, Steps From Duval! Key West villa offers easy access to numerous tourist spots in… More

From US$ 766 Book Now

Andros - Spacious 2X2 Waterfront Condo

Eisenhower Drive 915, Key West, United States Show map

During the stay at Andros - Spacious 2X2 Waterfront Condo Key West villa, guests can indulge in cycling and fisheries or visit the downtown commercial zoned Duval Street, located 20 minutes' walk… More

From US$ 876 Book Now

Good Vibrations By Last Key Realty

524 Dupont Lane, Key West, United States Show map

The 4-bedroom Good Vibrations By Last Key Realty Key West villa, located in close proximity to Key West Lighthouse and Keeper's Quarters Museum, can host up to 10 guests. Located merely 14 minutes'… More

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Pescado Penthouse

1201 Duval Street, Key West, United States Show map

Pescado Penthouse Villa Key West accommodates up to 9 guests and offers proximity to the downtown commercial zoned Duval Street, located 8 minutes' walk away. More

From US$ 1172 Book Now

Villa The Watson House

525 Simonton Street, Key West, United States Show map

The 4-bedroom Villa The Watson House Key West, located about a 5-minute walk from Key West Historic Seaport, can host up to 8 guests. This holiday home features opportunities for windsurfing… More

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Two Duval Street Suites W Parking And Pool

Duval Street 824, Key West, United States Show map

Located only 5 minutes on foot from The Ernest Hemingway Home and Museum, the 2-bedroom Two Duval Street Suites W Parking And Pool Key West villa provides an outdoor swimming pool as well as cycling… More

From US$ 807 Book Now

Renovated Corner Unit

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

Renovated Corner Unit Villa Key West, located 6 minutes' walk from San Carlos Institute, can host up to 4 guests. Located not far from Key West Butterfly and Nature Conservatory, this 2-bedroom villa… More

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Casa De Cuba

518 Virginia Street, Key West, United States Show map

Located just a 7-minute walk from the downtown commercial zoned Duval Street, the 3-bedroom Casa De Cuba Villa Key West is suitable for 6 guests and provides a heated pool to relax in. This 2… More

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Sweet Home Angelita By Last Key Realty

421 Angela Street, Key West, United States Show map

Up to 13 guests can stay at the 5-bedroom Sweet Home Angelita By Last Key Realty Key West and enjoy Southernmost Point of the Continental US Monument, located just a 6-minute walk away. Providing… More

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Atlantic Parrot

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

Located within 5 minutes' walk of The Key West Nature Preserve, Atlantic Parrot Villa Key West offers quick access to various city attractions in the vicinity. With a maximum capacity of 5 guests… More

From US$ 554 Book Now

Namaste

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

The 1-bedroom Namaste Villa Key West entices guests to enjoy windsurfing, snorkelling, and canyoning and offers proximity to Key West Historic Seaport, located approximately a 5-minute stroll away. More

From US$ 835 Book Now

Somewhere On The Beach

1800 Atlantic Blvd, Unit C238, Key West, United States Show map

Featuring an outdoor swimming pool, the 2-bedroom Somewhere On The Beach Key West villa is located nearly a 5-minute walk from The Key West Nature Preserve and is suitable for up to 6 guests. The… More

From US$ 972 Book Now

Dream Maker On The Atlantic

1800 Atlantic Blvd #C320, Key West, United States Show map

Featuring a heated pool, the 2-bedroom Dream Maker On The Atlantic Villa Key West is located approximately a 5-minute walk from The Key West Nature Preserve and is suitable for up to 6 guests. More

From US$ 813 Book Now

The Elizabeth Suite

1501 Truman Avenue 1, Key West, United States Show map

Featuring an outdoor swimming pool, the 1-bedroom The Elizabeth Suite Key West villa is located approximately 5 minutes' walk from Wreckers Sloop Mary and is suitable for up to 4 guests. Providing… More

From US$ 383 Book Now

Andy'S Attic

1016 Howe St #12, Key West, United States Show map

Along with proximity to The Ernest Hemingway Home and Museum, only a 5-minute walk away, the 1-bedroom Andy'S Attic Villa Key West offers opportunities for snorkelling and fisheries in the area. This… More

From US$ 365 Book Now

New! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking

Duval Street 1075, Key West, United States Show map

The 2-bedroom New! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking Key West entices guests to enjoy cycling and fisheries and offers proximity to Key West Butterfly and Nature… More

From US$ 718 Book Now

Key West On My Mind

1800 Atlantic Blvd Unit A305, Key West, United States Show map

Key West On My Mind Villa with a convenient location a 9-minute walk from Higgs Beach Dog Park entices guests with a hot tub and a sauna. Located 2.2 km from Key West Firehouse Museum, the 2-bedroom… More

From US$ 583 Book Now

Brand New Catchlight House With Private Pool

Mangrove Lane 7, Key West, United States Show map

During the stay at Brand New Catchlight House With Private Pool Villa Key West, guests can indulge in fisheries or visit Key West Tropical Forest and Botanical Garden, located a 15-minute walk away. More

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Casa Loca

535 Petronia Street, Key West, United States Show map

Featuring guided snorkelling trips to make your visit more entertaining, Casa Loca Villa Key West is 7 minutes' walk from the downtown commercial zoned Duval Street. Guests can enjoy windsurfing… More

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Always Your Paradise By Avantstay

620 Thomas Street #164, Key West, United States Show map

Situated just 6 minutes' walk from the downtown commercial zoned Duval Street, the 2-bedroom Always Your Paradise By Avantstay Key West villa is ideal for up to 4 guests. Providing guests with Wi-Fi… More

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Puerta Coralina By Last Key Realty

901 Grinnell Street, Key West, United States Show map

Located 750 metres from Fleming Street, Puerta Coralina By Last Key Realty Key West villa is suitable for 6 guests and provides a swimming pool to relax in. Situated in the Downtown Key West district… More

From US$ 1500 Book Now

Carey'S Corner

1016 Howe St #10, Key West, United States Show map

During the stay at Carey'S Corner Villa Key West, guests can indulge in snorkelling and fisheries or visit the natural history museum "Florida Keys Eco-Discovery Center", located a 13-minute walk… More

From US$ 406 Book Now

The Mesa House-Close To Duval!

Simonton Street 220, Key West, United States Show map

The 3-bedroom The Mesa House-Close To Duval! Key West villa is nestled a mere 6 minutes' walk from Key West First Legal Rum Distillery and can accommodate up to 10 guests. Located 2.4 km from Higgs… More

From US$ 1393 Book Now

Pelican Suite | Cozy Cottage, Hot Tubs, Close To D

1330 Simonton Street #5, Key West, United States Show map

Situated about 25 minutes' walk from the Harry S. Truman Little White House, the 1-bedroom Pelican Suite | Cozy Cottage, Hot Tubs, Close To D Key West provides access to numerous tourist attractions… More

From US$ 620 Book Now

Upper Sunset North

801 Eisenhower Dr. #8, 8, Key West, United States Show map

Positioned only 1.9 km from bustling shopping destinations such as Mile Marker 0 Store, the 4-bedroom Upper Sunset North Villa Key West offers guests to use a car park. This Key West holiday home… More

From US$ 884 Book Now

Sugar Palm Suite At Travelers Palm Inn Key West

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

The 1-bedroom Sugar Palm Suite At Travelers Palm Inn Key West villa is located nearly a 15-minute walk from San Carlos Institute and provides an outdoor swimming pool, ensuring a relaxing stay. More

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Toon Hall Tropical Village

1400 Alberta St #A, Key West, United States Show map

Located just 8 minutes' walk from Higgs Beach, the 3-bedroom Toon Hall Tropical Village Key West villa offers a swimming pool for guests to relax by. The property features opportunities for… More

From US$ 1271 Book Now

Leo'S Lodge

1016 Howe St #7, Key West, United States Show map

The 1-bedroom Leo'S Lodge Key West accommodates up to 2 guests and offers proximity to The Ernest Hemingway Home and Museum, located approximately a 5-minute walk away. The villa features… More

From US$ 392 Book Now