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

Cool Breeze

199 Golf Club Drive, Key West, United States Show map

The 3-bedroom Cool Breeze Villa Key West offers quick access to such city attractions as Key West Golf Club, located merely a 5-minute walk away. This Key West holiday home boasts barbecue and a golf… More

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A Gulfstream Drift

105 Front Street #319, Key West, United States Show map

Situated a mere 9 minutes on foot from the waterfront Mallory Square, the 2-bedroom A Gulfstream Drift Villa Key West is suitable for 7 guests and provides a heated pool to relax in. Offering a lift… More

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Sunrise Suites 308

3625 Seaside Dr Apt 308, Key West, United States Show map

Situated 10 minutes' drive from Higgs Beach Dog Park, Sunrise Suites 308 Key West villa provides access to numerous tourist attractions in the area. More

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Midtown Mosaic By Last Key Realty

1322 Thompson Street, Key West, United States Show map

Located around 25 minutes' walk from the Harry S. Truman Little White House, the 4-bedroom Midtown Mosaic By Last Key Realty Key West villa has a heated pool and is ideal for up to 8 guests. More

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Old Town Key West Hot Tub Duval 4 Blocks

901 Eaton Street, Key West, United States Show map

Situated just an 8-minute walk from Key West First Legal Rum Distillery, the 4-bedroom Old Town Key West Hot Tub Duval 4 Blocks Villa offers a Jacuzzi and can accommodate up to 8 guests. Located… More

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Bayview Middle

801 Eisenhower Dr. #5, 5, Key West, United States Show map

The 3-bedroom Bayview Middle Villa Key West offers quick access to such tourist spots as Wreckers Sloop Mary, situated only a 5-minute walk away. This Key West holiday home boasts a picnic area and a… More

From US$ 1078 Book Now

Paradise Found

711 William Street, Key West, United States Show map

Offering a steam room and a sauna for a relaxing experience, Paradise Found Key West villa is located an 18-minute walk from the waterfront Mallory Square. The 2-bedroom holiday home features… More

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Easy Livin By Avantstay

314 Admirals Lane, Key West, United States Show map

Located a mere 0.9 km from the natural history museum "Florida Keys Eco-Discovery Center", the 3-bedroom Easy Livin By Avantstay Key West villa has an outdoor swimming pool and is ideal for up to 8… More

From US$ 681 Book Now

Colony Calypso

714 Olivia Street #4, Key West, United States Show map

Located a mere 7 minutes' walk from The Ernest Hemingway Home and Museum, the 1-bedroom Colony Calypso Villa Key West offers a heated pool for guests to relax by. The villa features opportunities for… More

From US$ 314 Book Now

Casa Amor

723 Catherine Street, Key West, United States Show map

Casa Amor Key West is located an 8-minute walk from Higgs Beach and offers guests to enjoy windsurfing, snorkelling, and canyoning. Offering a prime location in the Downtown Key West district, the 3… More

From US$ 1929 Book Now

Casa Rosa

331 Simonton Street, Key West, United States Show map

Located in the Downtown Key West district, 6 minutes' walk from US 1 Mile Marker 0, Casa Rosa Villa Key West offers pool views. Providing guests with Wi-Fi and parking, the 4-bedroom holiday home is… More

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Royal Haven

1310 Royal Street, Key West, United States Show map

Featuring guided snorkelling trips to make your visit more entertaining, Royal Haven Villa Key West is 12 minutes' walk from Southernmost Point of the Continental US Monument. Guests can enjoy… More

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Island Paradise

413 Virginia St, Key West, United States Show map

The 2-bedroom Island Paradise Key West villa is nestled within 5 minutes' walk of The Ernest Hemingway Home and Museum and entices guests with a Jacuzzi. Offering a prime location in the Duval… More

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Matecumbe Suite By Last Key Realty

329 William Street #5, Key West, United States Show map

Featuring a living area and a dining table, the 1-bedroom Matecumbe Suite By Last Key Realty Key West villa offers guests to enjoy a prime location just an 8-minute walk from Key West First Legal Rum… More

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An Island Retreat

403B Emma Street, Key West, United States Show map

Situated a mere 9 minutes' stroll from the downtown commercial zoned Duval Street, the 2-bedroom An Island Retreat Villa Key West ensures a great leisure experience by offering snorkelling and… More

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Casa Del Sol

1519 Johnson Street, Key West, United States Show map

Situated 0.7 km from White Street Pier, Casa Del Sol Villa Key West is ideal for up to 10 guests. The historic Key West Lighthouse is 10 minutes' drive from this 6-bedroom villa and Southernmost… More

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Villa Cubana By Last Key Realty

606 Truman Avenue #5, Key West, United States Show map

Located within a 700-metre distance of the downtown commercial zoned Duval Street, Villa Cubana By Last Key Realty Key West is suitable for 4 guests and provides a swimming pool to relax in. Located… More

From US$ 848 Book Now

A Sanctuary Home

271 Golf Club Drive, Key West, United States Show map

Located approximately a 5-minute stroll from Key West Golf Club, the 3-bedroom A Sanctuary Home Key West offers barbecue, a golf course, and a dining table for guests' enjoyment. Offering an outdoor… More

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Bc277Flr Sapphire Sabbatical

9 Sapphire Dr., Key West, United States Show map

During the stay at Bc277Flr Sapphire Sabbatical Villa Key West, guests can indulge in windsurfing, snorkelling, and canyoning or visit Boca Chica Beach, located 4.2 km away. More

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Hyatt Beach House

5051 Overseas Hwy, Key West, United States Show map

Located 6 km from The Ernest Hemingway Home and Museum, Hyatt Beach House Key West villa gives access to various tourist sites in the vicinity. More

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Cayo Calypso By Last Key Realty

1312 Laird Street, Key West, United States Show map

Staying at the 3-bedroom Cayo Calypso By Last Key Realty Key West villa, guests can visit Higgs Beach, which is only 1.1 km away. Offering guided snorkelling trips, the Key West holiday home can… More

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Citrus Queen At Custom House Inn

Duval Street 124, Key West, United States Show map

Situated within 5 minutes' walk of Key West Shipwreck Treasure Museum, Citrus Queen At Custom House Inn Key West villa offers easy access to numerous tourist spots in the area. More

From US$ 792 Book Now

Royal Poinciana Weekly Rental!

620 Thomas Street #292, Key West, United States Show map

The 1-bedroom Royal Poinciana Weekly Rental! Key West villa offers easy access to such tourist spots as San Carlos Institute, located only a 6-minute walk away. Providing guests with Wi-Fi and… More

From US$ 428 Book Now

Tortuga Suite By Last Key Realty

329 William Street #2, Key West, United States Show map

Nestled 13 minutes' walk from the Minor Saint Mary Star of the Sea Basilica, the 1-bedroom Tortuga Suite By Last Key Realty Key West villa is boasting a living area and a dining table for guests'… More

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Cool Change

3131 Eagle Avenue, Key West, United States Show map

Positioned 15 minutes' drive from bustling shopping destinations such as the waterfront Mallory Square, Cool Change Key West villa offers guests to use a private parking lot. More

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Island Opulence By Last Key Realty

2718 Harris Avenue, Key West, United States Show map

The 4-bedroom Island Opulence By Last Key Realty Key West villa offers easy access to such tourist spots as Grace Lutheran Church, located merely 5 minutes' walk away. Providing guests with Wi-Fi and… More

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Sunset Suite Colony

714 Olivia Street, Key West, United States Show map

At the 1-bedroom Sunset Suite Colony Key West villa, guests can enjoy windsurfing, snorkelling, and canyoning as well as a location nearly a 5-minute walk from The Ernest Hemingway Home and Museum. More

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Brand New The Greenmoor House With Pool

15 Shoreline Road, Key West, United States Show map

Featuring a swimming pool for guests' relaxation, the 6-bedroom Brand New The Greenmoor House With Pool Key West villa is located within 15 minutes' walk of Key West Tropical Forest and Botanical… More

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Tideview Haven

25 Key Haven Rd, Key West, United States Show map

Featuring a heated pool, the 5-bedroom Tideview Haven Villa Key West is suitable for up to 10 people and is located nearly a 25-minute walk from Key West Golf Club. Providing guests with Wi-Fi and… More

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Seaside Retreat

2865 Key Cove Dr., Key West, United States Show map

Seaside Retreat Villa Key West is located merely a 6-minute stroll from Dive Key West and offers guests to relish a terrace as well as an outdoor swimming pool. Featuring a Jacuzzi, the property is… More

From US$ 1139 Book Now

Atlantis House Suites

1401 Atlantic Blvd, Key West, United States Show map

The 2-bedroom Atlantis House Suites Key West villa can host up to 4 guests, boasting a prime location merely 1.8 km from iconic cultural attractions such as Key West Firehouse Museum. Located about a… More

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Adrift In Key West

620 Thomas Street, #195, Key West, United States Show map

Located just an 8-minute walk from The Ernest Hemingway Home and Museum, the 2-bedroom Adrift In Key West Villa boasts an outdoor swimming pool and can accommodate up to 4. Providing guests with Wi… More

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Casa Azul-Open Concept Home With Pool

Elizabeth Street 629, Key West, United States Show map

Situated in the Downtown Key West district of Key West, just 550 metres from San Carlos Institute, the 2-bedroom Casa Azul-Open Concept Home With Pool Key West comes with a swimming pool for guests… More

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Archipelago II

241 Southard Street, Key West, United States Show map

Located 8 minutes' walk from the downtown commercial zoned Duval Street, Archipelago II Key West villa is suitable for 6 guests and provides an outdoor swimming pool to relax in. Located in proximity… More

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Kw48 Hemingway

418 Whalton Lane, Key West, United States Show map

Featuring a hot tub, the 3-bedroom Kw48 Hemingway Villa Key West is located around 5 minutes' walk from The Ernest Hemingway Home and Museum and can host up to 6 guests. More

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Conch Republic Cottage

510 Petronia St, Key West, United States Show map

Situated only 7 minutes on foot from Key West Butterfly and Nature Conservatory, the 3-bedroom Conch Republic Cottage Key West ensures a great leisure experience by offering windsurfing, snorkelling,… More

From US$ 952 Book Now

Key West Hideaway Sleeps Up To 10 4 Bedroom And 4 Baths 2 Pools

916 Center St, Key West, Fl 33040, Usa, Key West, United States Show map

Key West Hideaway Sleeps Up To 10 4 Bedroom And 4 Baths 2 Pools villa is nestled within a 400-metre distance of the downtown commercial zoned Duval Street and can accommodate up to 10 guests. More

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The Duke And The Duchess By Last Key Realty

512 Catherine Street #1 & #2, Key West, United States Show map

Featuring a swimming pool, the 8-bedroom The Duke And The Duchess By Last Key Realty Key West villa is located merely 6 minutes' walk from Southernmost Point of the Continental US Monument and is… More

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Captain'S Wheel

203-1 Southard Street, Key West, United States Show map

Along with proximity to The Ernest Hemingway Home and Museum, merely 0.6 km away, the 2-bedroom Captain'S Wheel Key West villa offers opportunities for snorkelling and fisheries in the area. The Key… More

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Trumans Trove By Last Key Realty

110 Admirals Lane, Key West, United States Show map

Featuring a swimming pool, Trumans Trove By Last Key Realty Key West villa is suitable for up to 6 people and is located a 25-minute walk from Higgs Beach Dog Park. Providing guests with Wi-Fi and… More

From US$ 1216 Book Now

Shady Palms

1415 Petronia Street, Key West, United States Show map

The 2-bedroom Shady Palms Villa Key West entices guests to enjoy snorkelling, canyoning, and fisheries and offers proximity to Fleming Street, located just 9 minutes' stroll away. Featuring a terrace… More

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Angelas Eclectic Gallery By Last Key Realty

1017 Angela Street, Key West, United States Show map

Located approximately 400 metres from Southernmost Point of the Continental US Monument, the 3-bedroom Angelas Eclectic Gallery By Last Key Realty Key West villa boasts a swimming pool, a Jacuzzi for… More

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The Fairhaven House At Solaire Lunara Bay

14 Andrea Lane, Key West, United States Show map

The Fairhaven House At Solaire Lunara Bay Key West villa is located a 17-minute walk from Key Haven and invites guests to join fisheries. The 8-bedroom holiday home features a swimming pool and is… More

From US$ 4077 Book Now

Sweet Americana By Last Key Realty

524-526 Dupont Lane, Key West, United States Show map

Featuring a swimming pool, Sweet Americana By Last Key Realty Key West villa is suitable for up to 20 people and is located a 20-minute walk from Fort Zachary Taylor. Providing guests with Wi-Fi and… More

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Saltwater Harmony By Last Key Realty

620 Thomas Street #162, Key West, United States Show map

Offering a location within 25 minutes' walk of the historic fort "West Martello Tower", the 2-bedroom Saltwater Harmony By Last Key Realty Key West villa gives access to various tourist spots in the… More

From US$ 774 Book Now

Forever Young

115 Front Street, #202, Key West, United States Show map

The 2-bedroom Forever Young Key West villa is situated nearly 5 minutes' walk from Front Street, featuring such comforts as Wi-Fi and a private parking lot. Offering a prime location in the Downtown… More

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Linger Longer By Avantstay

277 Southard Street, Key West, United States Show map

Situated in the Downtown Key West district of Key West, nearly 20 minutes' walk from Bayview Park, the 2-bedroom Linger Longer By Avantstay Key West villa comes with an outdoor swimming pool for… More

From US$ 400 Book Now

Kw270Flr The Southernmost Comfort House

202 Admirals Lane, Key West, United States Show map

Located only a 9-minute walk from the waterfront Mallory Square, the 4-bedroom Kw270Flr The Southernmost Comfort House Key West villa boasts a swimming pool and can accommodate up to 10. The holiday… More

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Sunset South

801 Eisenhower Dr. #1, 1, Key West, United States Show map

Featuring a heated pool, Sunset South Villa Key West is suitable for up to 4 people and is located 18 minutes' walk from the downtown commercial zoned Duval Street. Providing guests with Wi-Fi and a… More

From US$ 474 Book Now

Conch Cove

720 Rr Simonton Lane, Key West, United States Show map

Along with proximity to the even Southernmost Point, only a 6-minute walk away, the 3-bedroom Conch Cove Villa Key West offers opportunities for snorkelling and fisheries in the area. The… More

From US$ 2178 Book Now