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2026-11-06
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Holiday Homes in Key West

Spacious 52' Sailboat | 6 Cabins | Dockside Escape

7005 Shrimp Road, Key West, United States Show map

The 6-bedroom Spacious 52' Sailboat | 6 Cabins | Dockside Escape Key West is situated about 5 minutes' walk from the newly developed Stock Island Marina Village, featuring such comforts as Wi-Fi and… More

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Lighthouse Villa By Avantstay

921 Whitehead Street, Key West, United States Show map

Offering an outdoor swimming pool, Lighthouse Villa By Avantstay Key West is situated only 8 minutes' walk from Key West Butterfly and Nature Conservatory and can accommodate up to 8 guests. More

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Island Style Colony

714 Olivia St, Key West, United States Show map

Located 0.6 km from the downtown commercial zoned Duval Street, Island Style Colony Villa Key West boasts a swimming pool and can accommodate up to 4. This 1-bedroom villa features opportunities for… More

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Noonas Mansion By Last Key Realty

510 Noah Lane, Key West, United States Show map

Located merely a 7-minute walk from Fort Zachary Taylor, Noonas Mansion By Last Key Realty Key West villa features a heated pool and can accommodate up to 8 guests. Located 2.5 km from the even… More

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La Brisa Unit 105 North Building

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

Offering access to entertainment venues such as the performing arts theater "Red Barn Theatre", situated nearly a 10-minute drive away, the 1-bedroom La Brisa Unit 105 North Building Villa Key West… More

From US$ 741 Book Now

Conch Keys | Private Pool & Outdoor Bar Paradise!

1401 Flagler Avenue, Key West, United States Show map

The 2-bedroom Conch Keys | Private Pool & Outdoor Bar Paradise! Key West villa is located nearly 25 minutes' walk from the bustling plaza "Mallory Square", giving access to various tourist spots… More

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Green Spot

620 Thomas Street #258, Key West, United States Show map

Located only an 8-minute walk from The Ernest Hemingway Home and Museum, the 2-bedroom Green Spot Key West villa features an outdoor swimming pool and can accommodate up to 4 guests. This holiday… More

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Sunset Dalite

109 Front Street #212, Key West, United States Show map

Situated approximately 5 minutes' walk from the fully accredited Mel Fisher Maritime Heritage Museum, the 2-bedroom Sunset Dalite Villa Key West is ideal for up to 4 guests. Providing guests with Wi… More

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Kw271Flr Sunset Bay

H31 Miriam St., Key West, United States Show map

Kw271Flr Sunset Bay Villa Key West is located a 10-minute walk from Thompson Island and invites guests to join snorkelling, diving, and canyoning. The 3-bedroom villa hosts up to 11 guests and… More

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A Palm Tree Paradise

7 Spoonbill Way, Key West, United States Show map

Offering an outdoor swimming pool, the 2-bedroom A Palm Tree Paradise Key West villa is situated approximately 10 minutes' walk from Key West Tropical Forest and Botanical Garden and can accommodate… More

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Alligator Reef Light Suite

419 Truman Avenue, Key West, United States Show map

Situated a mere 7 minutes' stroll from Key West Butterfly and Nature Conservatory, the 2-bedroom Alligator Reef Light Suite Key West villa ensures a great leisure experience by offering cycling and… More

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Ahoy Mate!

210-1 Southard Street, Key West, United States Show map

Staying at the 2-bedroom Ahoy Mate! Villa Key West, guests can visit Key West Butterfly and Nature Conservatory, which is just 1.2 km away. Offering a private parking lot as well as Wi-Fi, the Key… More

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Old Town Proximity - Island Serenity!

28 Merganser Ln, Key West, United States Show map

The 2-bedroom Old Town Proximity - Island Serenity! Key West villa is located about 20 minutes' walk from Safe Harbor and provides an outdoor swimming pool, ensuring a relaxing stay. With a maximum… More

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Seaport Sensation By Last Key Realty

121 Simonton Street, Key West, United States Show map

Staying at the 3-bedroom Seaport Sensation By Last Key Realty Key West villa, guests can visit the downtown commercial zoned Duval Street, which is only 1 km away. Offering guided snorkelling trips… More

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Beautiful Downtown Truman Annex Condo

210-5 Southard Street, Key West, United States Show map

Beautiful Downtown Truman Annex Condo Key West villa is located an 8-minute walk from the Harry S. Truman Little White House and invites guests to enjoy massage therapy and a golf course. The 2… More

From US$ 383 Book Now

Takeover At The Grand Maloney

Caroline Street 529, Key West, United States Show map

Located just a 9-minute walk from the downtown commercial zoned Duval Street, the 6-bedroom Takeover At The Grand Maloney Key West villa is suitable for 16 guests and provides a swimming pool to… More

From US$ 4224 Book Now

The Poetic Pineapple By Last Key Realty

4 Aronovitz Lane, Key West, United States Show map

Featuring a swimming pool, The Poetic Pineapple By Last Key Realty Key West villa is suitable for up to 4 people and is located an 18-minute walk from the bustling plaza "Mallory Square". More

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Serenity By Avantstay

907 Emma St, Key West, United States Show map

Offering an outdoor swimming pool, Serenity By Avantstay Key West villa is located about 5 minutes' walk from The Ernest Hemingway Home and Museum and is ideal for up to 2 guests. This 1-bedroom… More

From US$ 204 Book Now

Another Siesta

620 Thomas St #168, Key West, United States Show map

The 1-bedroom Another Siesta Key West villa accommodates up to 2 guests and offers proximity to The Ernest Hemingway Home and Museum, located merely 0.6 km away. Providing guests with Wi-Fi and a… More

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Sailor'S Son

2867 Key Cove Dr., Key West, United States Show map

Featuring a heated pool, Sailor'S Son Villa Key West is suitable for up to 8 people and is located nearly a 25-minute walk from Key West Tropical Forest and Botanical Garden. Providing guests with Wi… More

From US$ 1325 Book Now

Relaxing Island Home Great Location Stylish

Olivia Street 709, Key West, United States Show map

Offering access to entertainment venues such as Papa's Pilar Rum Distillery, situated only 1.4 km away, the 1-bedroom Relaxing Island Home Great Location Stylish Key West can host up to 4 guests. More

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Walkable Cottage W/ Pool Access In Key West!

620 Thomas St Unit 108, Key West, United States Show map

Featuring an outdoor swimming pool, Walkable Cottage W/ Pool Access In Key West! is suitable for up to 6 people and is located a 14-minute walk from the waterfront Mallory Square. More

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Casa Amarilla By Last Key Realty

516 Catherine Street, Key West, United States Show map

The 3-bedroom Casa Amarilla By Last Key Realty Key West is nestled about a 5-minute walk from Key West Butterfly and Nature Conservatory and can accommodate up to 6 guests. Located 2.5 km from… More

From US$ 761 Book Now

Amberjack

253 Southard Street, Key West, United States Show map

The 2-bedroom Amberjack Villa Key West is nestled only a 9-minute walk from the downtown commercial zoned Duval Street and can accommodate up to 6 guests. Located a short way from Fort Zachary Taylor… More

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Casa Blanca

1112 Watson Street, Key West, United States Show map

The 4-bedroom Casa Blanca Villa Key West entices guests to enjoy windsurfing, snorkelling, and canyoning and offers proximity to Higgs Beach, located just 8 minutes' stroll away. The Key West holiday… More

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Caribbean Cottage 28 Day Minimum Rental 2Br 2Ba Heated Pools

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

Located around a 5-minute stroll from the historic Key West Lighthouse, the 2-bedroom Caribbean Cottage 28 Day Minimum Rental 2Br 2Ba Heated Pools Key West gives easy access to various tourist… More

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Night Watch @ Speakeasy Inn Key West!

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

Night Watch @ Speakeasy Inn Key West! villa is located 20 minutes' walk from Bayview Park and invites guests to join snorkelling and fisheries. Offering a car park as well as Wi-Fi, the 1-bedroom… More

From US$ 376 Book Now

Star Of The Seaport By Last Key Realty

621 Caroline Street, Key West, United States Show map

Along with access to such natural sites as Key West Butterfly and Nature Conservatory, only 1.8 km away, the 5-bedroom Star Of The Seaport By Last Key Realty Key West villa offers a heated pool. With… More

From US$ 2893 Book Now

The Enchanted Rose By Last Key Realty

1613 Rose Street, Key West, United States Show map

The 3-bedroom The Enchanted Rose By Last Key Realty Key West villa is nestled around a 5-minute walk from Higgs Beach Dog Park and can accommodate up to 10 guests. Located 2.2 km from Key West… More

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The Tahiti Suite - Updated Key West Condo With Pool, Hot Tub, & Balcony!

3625 Seaside Drive #104, Key West, United States Show map

Located about a 25-minute walk from Sheriff s Animal Farm, The Tahiti Suite - Updated Key West Condo With Pool, Hot Tub, & Balcony! villa gives access to various tourist sites in the vicinity. More

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Nautical Wheeler

2869 Key Cove Drive, Key West, United States Show map

Nautical Wheeler Villa Key West is located 25 minutes' walk from Higgs Beach Dog Park and provides an outdoor swimming pool, ensuring a relaxing stay. Suitable for 8 guests, the 4-bedroom holiday… More

From US$ 2027 Book Now

Golf Villa

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

The 2-bedroom Golf Villa Key West offers proximity to such city sites as FYT Fitness Center, located nearly a 5-minute walk away. Providing guests with Wi-Fi and private car parking, this property is… More

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A Poolside Cabana

2 Kestral Way, Key West, United States Show map

A Poolside Cabana Key West, located merely a 5-minute walk from FYT Fitness Center, can host up to 4 guests. Located a mere 1.9 km from Safe Harbor, the 2-bedroom holiday home provides Wi-Fi and… More

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Hidden Oasis Colony

714 Olivia St, Key West, United States Show map

Located just a 7-minute walk from the downtown commercial zoned Duval Street, the 1-bedroom Hidden Oasis Colony Villa Key West is suitable for 4 guests and provides a swimming pool to relax in. This… More

From US$ 406 Book Now

Papa'S Casita

405 Olivia Street, Key West, United States Show map

Located in close proximity to The Ernest Hemingway Home and Museum, Papa'S Casita Villa Key West has a heated pool and is ideal for up to 6 guests. Offering private car parking as well as Wi-Fi, this… More

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A Bit Of Heaven

1115 Southard Street, Key West, United States Show map

The 3-bedroom A Bit Of Heaven Villa Key West is located just a 9-minute walk from Fleming Street and invites guests to enjoy guided snorkelling trips. This villa features opportunities for… More

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Kw275Flr Tropical Vibes

1216 Margaret St., Key West, United States Show map

Located merely a 9-minute walk from Key West Butterfly and Nature Conservatory, the 4-bedroom Kw275Flr Tropical Vibes Villa Key West features a private outdoor pool and can accommodate up to 8 guests… More

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Kw230 Last Minute

219 Whitehead St. (Rear), Key West, United States Show map

Located about a 5-minute walk from The Oldest House Historical Place Museum, the 3-bedroom Kw230 Last Minute Key West villa offers a private outdoor swimming pool for guests to relax by. The holiday… More

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A & E'S Tranquil Tides

620 Thomas Street #190, Key West, United States Show map

The 2-bedroom A & E'S Tranquil Tides Villa Key West accommodates up to 4 guests and offers proximity to the downtown commercial zoned Duval Street, located only a 6-minute walk away. This Key West… More

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Island Oasis

101 Front Street, #25, Key West, United States Show map

Situated in the Downtown Key West district of Key West, within 10 minutes' walk of the downtown commercial zoned Duval Street, the 2-bedroom Island Oasis Villa Key West comes with an outdoor swimming… More

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Old Town Garden Villas

1001 Whitehead St., Key West, United States Show map

Located a mere 500 metres from the historic Saint Mary Star of the Sea Church, Old Town Garden Villas Key West offers quick access to various city attractions in the vicinity. More

From US$ 418 Book Now

Blue Heron By Avantstay

906-2 Truman Avenue, Key West, United States Show map

Featuring an outdoor swimming pool as well as views of the pool, the welcoming Blue Heron By Avantstay Key West villa offers a prime location just a 5-minute walk from the Minor Saint Mary Star of… More

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Family House 2 Bedroom Private Spa 2 Heated Pools

912 Center Street, Key West, United States Show map

The 2-bedroom Family House 2 Bedroom Private Spa 2 Heated Pools Key West villa is nestled within 5 minutes' walk of the historic Key West Lighthouse and entices guests with a Jacuzzi. Offering Wi-Fi,… More

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Kw31 Three Flowers Guesthouse

521 Simonton St, Key West, United States Show map

Kw31 Three Flowers Guesthouse Key West villa, located fairly close to Nancy Forrester's Secret Garden, can host up to 14 guests. More

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Booty Caye

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

Offering a location nearly 5 minutes' walk from FYT Fitness Center, the 2-bedroom Booty Caye Villa Key West gives access to various tourist spots in the area. Guests can enjoy windsurfing… More

From US$ 179 Book Now

1 Island Time Escape

101 Front Street, #15, Key West, United States Show map

Situated nearly a 5-minute stroll from the Harry S. Truman Little White House, the 2-bedroom 1 Island Time Escape Villa Key West ensures a great leisure experience by offering snorkelling and… More

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The Caroline Suite

1501 Truman Avenue 2, Key West, United States Show map

Up to 4 guests can stay at the 1-bedroom The Caroline Suite Key West villa and enjoy Wreckers Sloop Mary, located merely a 5-minute walk away. Providing guests with Wi-Fi and parking, the property is… More

From US$ 514 Book Now

South St Cottage

1305 South Street, Key West, United States Show map

Situated a mere 8 minutes' stroll from Higgs Beach, the 2-bedroom South St Cottage Key West can welcome up to 4 guests and boasts a Jacuzzi for a relaxing retreat. Offering a swimming pool, the Key… More

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Southernmost Palms By Last Key Realty

101 Front Street #24, Key West, United States Show map

Featuring a swimming pool, the 2-bedroom Southernmost Palms By Last Key Realty Key West villa is located approximately 5 minutes' walk from the bustling plaza "Mallory Square" and is suitable for up… More

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A Windsong Delight

1017 Windsor Lane #2, Key West, United States Show map

Situated in the Downtown Key West district of Key West, merely 1.6 km from The Ernest Hemingway Home and Museum, the 2-bedroom A Windsong Delight Villa Key West comes with a swimming pool for guests… More

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