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

Conch Casa Grande By Last Key Realty

58 Front Street, Key West, United States Show map

Featuring a swimming pool, Conch Casa Grande By Last Key Realty Key West is suitable for up to 8 people and is located a 25-minute walk from Mile Marker 0 Store. Providing guests with Wi-Fi and… More

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Calusa Suite By Last Key Realty

329 William Street #6, Key West, United States Show map

Situated a 9-minute walk from US 1 Mile Marker 0, Calusa Suite By Last Key Realty Key West villa offers guests to relax by a heated pool. Offering a prime location in the Downtown Key West district… More

From US$ 528 Book Now

Tumis Time Out By Avantstay

606 Truman Ave #4, Key West, United States Show map

Located in the Duval district, a 6-minute walk from Saint Mary Star of the Sea Basilica, Tumis Time Out By Avantstay Key West villa offers pool views. Providing guests with Wi-Fi and parking, the 2… More

From US$ 251 Book Now

A Palm Oasis

405 Emma Street Unit B, Key West, United States Show map

Along with proximity to the Harry S. Truman Little White House, just 0.7 km away, the 2-bedroom A Palm Oasis Villa Key West offers opportunities for snorkelling and fisheries in the area. Providing… More

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Kw287Flr Keys Please

1408 Petronia St., Key West, United States Show map

Featuring a heated pool, the 3-bedroom Kw287Flr Keys Please Villa Key West is located approximately 5 minutes' walk from Wreckers Sloop Mary and is suitable for up to 6 guests. Guests can enjoy… More

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Kw319Flr Happy Hour Haven

620 Thomas St #285, Key West, United States Show map

Along with proximity to The Ernest Hemingway Home and Museum, merely 0.6 km away, the 2-bedroom Kw319Flr Happy Hour Haven Villa Key West offers opportunities for windsurfing, snorkelling, and diving… More

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Endless Summer By Last Key Realty

522 Dupont Lane, Key West, United States Show map

Offering a swimming pool, the 5-bedroom Endless Summer By Last Key Realty Key West villa is located merely 6 minutes' walk from the even Southernmost Point and is ideal for up to 12 guests. Located… More

From US$ 3258 Book Now

The Grande Vista

1800 Atlantic Blvd Unit C432, Key West, United States Show map

Up to 6 guests can stay at the 2-bedroom The Grande Vista Villa Key West and enjoy The Key West Nature Preserve, located approximately a 5-minute walk away. Featuring a hot tub and a sauna, the… More

From US$ 715 Book Now

American Shoal Light Suite

419 Truman Avenue, Key West, United States Show map

Located in the Downtown Key West district, 5 minutes' walk from the downtown commercial zoned Duval Street, American Shoal Light Suite Key West villa offers city views. The 2-bedroom holiday home… More

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Layover In Paradise By Last Key Realty

821 Waddell Street, Key West, United States Show map

Situated just a 7-minute stroll from Key West Firehouse Museum, the 3-bedroom Layover In Paradise By Last Key Realty Key West villa is suitable for 8 guests and provides a swimming pool to relax in. More

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The Green Gawdess

1325 Whitehead Street, Key West, United States Show map

Up to 8 guests can stay at the 4-bedroom The Green Gawdess Key West villa and enjoy Key West Lighthouse and Keeper's Quarters Museum, located about a 5-minute walk away. The property features… More

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Passover Cottage

Passover Lane, Key West, United States Show map

Featuring a swimming pool, the 2-bedroom Passover Cottage Key West is located around a 5-minute walk from the very unusual Key West Cemetery and is suitable for up to 4 guests. More

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Unique Floating Accommodation At Resort For Getaway To Key West, Florida

7009 Shrimp Rd. S-1, Key West, United States Show map

Situated within 7 km of The Ernest Hemingway Home and Museum, the 1-bedroom Unique Floating Accommodation At Resort For Getaway To Key West, Florida villa offers guests to enjoy a patio and a golf… More

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Starfish

803 Catherine Street, Key West, United States Show map

The 2-bedroom Starfish Villa Key West hosts up to 6 guests and provides proximity to Higgs Beach, situated just 650 metres away. This Key West villa features opportunities for windsurfing… More

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Ascension Truman Annex

225 Southard Street, Key West, United States Show map

Located only 8 minutes on foot from the downtown commercial zoned Duval Street, the 2-bedroom Ascension Truman Annex Key West villa provides an outdoor swimming pool as well as snorkelling and… More

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A License To Chill

101 Front Street, #12, Key West, United States Show map

Located within a 700-metre distance of the waterfront Mallory Square, A License To Chill Villa Key West is suitable for 6 guests and provides an outdoor swimming pool to relax in. The 2-bedroom villa… More

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Elegant Escape By Last Key Realty

500 Emma Street, Key West, United States Show map

Located merely 0.6 km from Fort Zachary Taylor, the 4-bedroom Elegant Escape By Last Key Realty Key West villa offers a swimming pool for guests to relax by. Providing guests with Wi-Fi and a private… More

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Flagler Station

1430 Flagler Ave., Key West, United States Show map

Offering a location 2.5 km from the bustling plaza "Mallory Square", Flagler Station Villa Key West gives access to various tourist spots in the area. More

From US$ 290 Book Now

Pelican'S Perch

202-1 Southard Street, Key West, United States Show map

Featuring an outdoor swimming pool, Pelican'S Perch Key West villa is suitable for up to 6 people and is located 15 minutes' walk from Key West Butterfly and Nature Conservatory. Providing guests… More

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Blackbeard'S Hideaway

Blackbeard Lane, Key West, United States Show map

Located 850 metres from American Shoal Lighthouse, Blackbeard'S Hideaway Key West villa gives access to various tourist sites in the vicinity. The 2-bedroom holiday home hosts up to 6 guests and… More

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The Zesty Lime By Last Key Realty

421 Simonton Street, Key West, United States Show map

Staying at the 3-bedroom The Zesty Lime By Last Key Realty Key West villa, guests can visit Mile Marker 0 Store, which is only 0.8 km away. The Key West holiday home features a heated pool and is… More

From US$ 2356 Book Now

Tailgate Key

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

Situated approximately 5 minutes' walk from FYT Fitness Center, the 2-bedroom Tailgate Key Villa Key West offers easy access to numerous tourist spots in the area. Providing guests with Wi-Fi and a… More

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Plantation Tropicale By Last Key Realty

1430 Tropical Street, Key West, United States Show map

The 5-bedroom Plantation Tropicale By Last Key Realty Key West villa hosts up to 12 guests and provides proximity to Higgs Beach, situated just 0.6 km away. More

From US$ 1619 Book Now

Bachelorparty Hq For 16-Feet To Duval-Pool-Hot Tub

Truman Avenue 417, Key West, United States Show map

The 5-bedroom Bachelorparty Hq For 16-Feet To Duval-Pool-Hot Tub Villa Key West is located around a 15-minute walk from Memorial Sculpture Garden and provides an outdoor swimming pool, ensuring a… More

From US$ 1984 Book Now

Royal Escape

1307 Royal St, Key West, United States Show map

Offering an outdoor swimming pool, the 3-bedroom Royal Escape Villa Key West is located a mere 8 minutes' walk from Higgs Beach and is ideal for up to 10 guests. This 3-bathroom villa features… More

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Casita Olivietta By Last Key Realty

805 Olivia Street, Key West, United States Show map

Situated only 6 minutes' stroll from Southernmost Point of the Continental US Monument, the 3-bedroom Casita Olivietta By Last Key Realty Key West villa is suitable for 8 guests and provides a heated… More

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Old Town Getaway

730 Passover Lane, Key West, United States Show map

Up to 4 guests can stay at the 1-bedroom Old Town Getaway Villa Key West and enjoy Papa's Pilar Rum Distillery, located approximately 500 metres away. Located merely 5 minutes' walk from the 19… More

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Salt Pond Hideaway | Comfortable Condo With Pool!

3675 Seaside Drive #133, Key West, United States Show map

Staying at the 2-bedroom Salt Pond Hideaway | Comfortable Condo With Pool! Key West villa, guests can easily reach State Harbor, located a mere 1.8 km away. This Key West holiday home is suitable for… More

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Tortugas Harbor Light Suite

419 Truman Avenue, Key West, United States Show map

Located only a 5-minute walk from the downtown commercial zoned Duval Street, Tortugas Harbor Light Suite Key West villa offers cycling and fisheries to diversify guests' leisure. Offering city views… More

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Walkable Old Town Home With Tropical Patio

834 Olivia Street, Key West, United States Show map

Staying at Walkable Old Town Home With Tropical Patio Key West, guests can visit Smathers Beach, which is nearly a 25-minute walk away. More

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Margarets Magic Compound By Last Key Realty

515-517 Margaret Street, Key West, United States Show map

Located merely an 8-minute walk from Key West First Legal Rum Distillery, Margarets Magic Compound By Last Key Realty Key West villa features a heated pool and can accommodate up to 8 guests. More

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Villa Positano -Rooftop Pool On Duval

Duval Street 1075, Key West, United States Show map

Villa Positano -Rooftop Pool On Duval Key West offers swift access to various city sites, such as Key West Lighthouse and Keeper's Quarters Museum, situated approximately 5 minutes' walk away. More

From US$ 762 Book Now

Ashe Street Serenade

613 Ashe Street, Key West, United States Show map

Located within 5 minutes' walk of The Unitarian Universalist Fellowship of Key West, the 3-bedroom Ashe Street Serenade Key West villa offers quick access to various city attractions in the vicinity.… More

From US$ 390 Book Now

Old Town Home A Short Walk To Duval Couples Oasis

Olivia Street 709, Key West, United States Show map

The 1-bedroom Old Town Home A Short Walk To Duval Couples Oasis Key West accommodates up to 4 guests and offers proximity to the downtown commercial zoned Duval Street, located only 7 minutes' walk… More

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A Sunset Celebration

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

Featuring an outdoor swimming pool, the 3-bedroom A Sunset Celebration Villa Key West is suitable for up to 5 people and is located nearly a 20-minute walk from Key West Tropical Forest and Botanical… More

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Blue Heaven

620 Thomas St., #251, Key West, United States Show map

The 2-bedroom Blue Heaven Villa Key West entices guests to enjoy snorkelling and fisheries and offers proximity to the downtown commercial zoned Duval Street, located only 6 minutes' stroll away. More

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Aqua Breeze

105 Front Street #219, Key West, United States Show map

Offering a heated pool, the 2-bedroom Aqua Breeze Villa Key West is located approximately a 5-minute walk from the fully accredited Mel Fisher Maritime Heritage Museum and is ideal for up to 5 guests… More

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The Contented Crane By Last Key Realty

909 Windsor Lane, Key West, United States Show map

Offering a swimming pool, the 3-bedroom The Contented Crane By Last Key Realty Key West villa is located merely 6 minutes' walk from the even Southernmost Point and is ideal for up to 8 guests. More

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Waterfront Luxury Home - Tidelands House

8 Key Haven Terrace, Key West, United States Show map

Featuring a swimming pool, the 8-bedroom Waterfront Luxury Home - Tidelands House Key West is suitable for up to 16 people and is located within 10 minutes' drive of Smathers Beach. This Key West… More

From US$ 2333 Book Now

Charming 'Boho Breeze' Retreat W/ Pool Access

171 Golf Club Dr, Key West, United States Show map

Offering a patio and a golf course for guests' leisure, Charming 'Boho Breeze' Retreat W/ Pool Access Villa Key West is situated 20 minutes' walk from Key West Tropical Forest and Botanical Garden. More

From US$ 145 Book Now

A Sunset Peace

109 Front Street #210, Key West, United States Show map

Offering a heated pool, the 2-bedroom A Sunset Peace Villa Key West is located nearly a 5-minute walk from Audubon House and Tropical Gardens and is ideal for up to 4 guests. The holiday home… More

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Coconut Palm Studio At Travelers Palm Inn Key West

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

The 1-bedroom Coconut Palm Studio At Travelers Palm Inn Key West villa hosts up to 2 guests and provides proximity to Key West Butterfly and Nature Conservatory, situated only a 9-minute walk away. More

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The Curry House - Entire Complex

Fleming Street 806, Key West, United States Show map

Featuring a swimming pool, the 9-bedroom The Curry House - Entire Complex Villa Key West is suitable for up to 18 people and is located 16 minutes' walk from Southernmost Point of the Continental US… More

From US$ 1415 Book Now

Havana House By Last Key Realty

915 Grinnell Street, Key West, United States Show map

Offering a heated pool, the 3-bedroom Havana House By Last Key Realty Key West villa is located merely 9 minutes' walk from Fleming Street and is ideal for up to 8 guests. Located in the Downtown Key… More

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Rigby House - Brand New With Private Pool

Simonton Street 218, Key West, United States Show map

The 6-bedroom Rigby House - Brand New With Private Pool Villa Key West is located only 1.4 km from The Ernest Hemingway Home and Museum and has an aqua park and a golf course to ensure a memorable… More

From US$ 3023 Book Now

Tropical Executive

107 Front Street #116, Key West, United States Show map

Located only a 9-minute stroll from the bustling plaza "Mallory Square", the 2-bedroom Tropical Executive Villa Key West provides a heated pool as well as snorkelling and fisheries to diversify… More

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Dancing Palms

518 Porter Lane, Key West, United States Show map

The 2-bedroom Dancing Palms Villa Key West is nestled just a 9-minute walk from the Harry S. Truman Little White House and can accommodate up to 4 guests. Located not far from Key West First Legal… More

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New Rose Retreat - Pool & Parking

Rose Lane 526, Key West, United States Show map

Located just 0.6 km from Key West First Legal Rum Distillery, the 2-bedroom New Rose Retreat - Pool & Parking Villa Key West boasts an outdoor swimming pool and can accommodate up to 6. Providing… More

From US$ 741 Book Now

Tropical Hideaway - Private Pool

1006 Seminary Street, Key West, United States Show map

Overlooking the city, Tropical Hideaway - Private Pool Villa Key West enjoys a prime setting merely a 5-minute walk from Key West Firehouse Museum. More

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Heron House - Luxury Waterfront Home

Bamboo Terrace 12, Key West, United States Show map

Situated about 500 metres from FYT Fitness Center, Heron House - Luxury Waterfront Home Key West offers easy access to numerous tourist spots in the area. More

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