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2026-04-19
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Vacation Rentals in Key West

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 Harry S. Truman Little White House, located 15 minutes' walk away. More

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Aloha

822 Washington Street, Key West, United States View map

**Experience the Serenity of Aloha Villa Key West** With its prime location, Aloha Villa Key West effortlessly connects you to the area's picturesque beaches and lively attractions. More

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Blackbeard'S Hideaway

Blackbeard Lane, Key West, United States View map

Situated nearly a 25-minute walk from Gopher Key, the 1-bedroom Blackbeard'S Hideaway Key West villa provides access to numerous tourist attractions in the area. More

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The Admirals Estate By Last Key Realty

324 Whitehead Street, Key West, United States View map

Staying at the 5-bedroom The Admirals Estate By Last Key Realty Key West villa, guests can visit Key West Firehouse Museum, which is nearly 25 minutes' walk away. More

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Charmayne'S Cottages - Truman @ Duval

423 Truman Avenue, Key West, United States View map

Offering a location just a 5-minute walk from Key West Lighthouse and Keeper's Quarters Museum, Charmayne'S Cottages - Truman @ Duval Key West gives access to various tourist spots in the area. More

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A Harbour Roost

109 Front Street #114, Key West, United States View map

Situated a mere 6 minutes on foot from the Curry Mansion, A Harbour Roost Villa Key West offers easy access to numerous tourist spots in the area. More

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Kokomo Suite By Last Key Realty

329 William Street #1, Key West, United States View map

Located 750 metres from Key West Cemetery, Kokomo Suite By Last Key Realty Key West villa offers a heated swimming pool for guests to relax by. More

From US$ 297 Book Now

A Sunset And Harbour View

115 Front Street #204, Key West, United States View map

Staying at A Sunset And Harbour View Villa Key West, guests can visit the USCGC Ingham Maritime Museum, which is just 1.1 km away. More

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Perfect Harmony By Last Key Realty

1200 Florida Street, Key West, United States View map

Featuring a private swimming pool for guests' relaxation, the 3-bedroom Perfect Harmony By Last Key Realty Key West villa is located around 20 minutes on foot from Key West Lighthouse. More

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Sun, Sea, And Sky

202-5 Southard Street, Key West, United States View map

Located only 7 minutes' walk from the downtown commercial zoned Duval Street, Sun, Sea, And Sky Villa Key West offers opportunities for snorkelling and fishing in the area. Situated in the Downtown… More

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Helluva Happy Place

315 Catherine St, Key West, United States View map

The 2-bedroom Helluva Happy Place Key West villa provides easy access to various city attractions, such as the Southernmost Point, situated a mere 6 minutes' walk away. More

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Beachy Keen Too

1500 Atlantic Boulevard #304, Key West, United States View map

Located a 5-minute drive from the Key West Butterfly and Nature Conservatory, Beachy Keen Too Key West villa gives access to various tourist sites in the vicinity. More

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Shady Palms

1415 Petronia Street, Key West, United States View map

The 2-bedroom Shady Palms Villa Key West offers swift access to various city sites, such as Wreckers Sloop Mary, situated about 5 minutes' walk away. Located just 0.7 km from C. B. Harvey Rest Beach… More

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Summer Solstice By Last Key Realty

522-524 Dupont Lane, Key West, United States View map

The 10-bedroom Summer Solstice By Last Key Realty Key West villa offers proximity to such city sites as Southernmost Point of the Continental US, located only 6 minutes' walk away. More

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Golf Villa

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

The 2-bedroom Golf Villa Key West offers quick access to such tourist spots as Key Haven, situated only a 5-minute walk away. Providing guests with Wi-Fi and a free private car park, this… More

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A Palm Oasis

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

Located 13 minutes' walk from the Key West Aquarium, A Palm Oasis Villa Key West gives access to various tourist sites in the vicinity. More

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Beach Club Oasis #304

1500 Atlantic Blvd #304, Key West, United States View map

The beachfront Beach Club Oasis #304 Key West apartment entices guests with a spa centre merely a 5-minute walk from the Higgs Beach Dog Park. This apartment features Wi-Fi throughout the property. More

From US$ 626 Book Now

Blue Horizon Hideaway

3029 North Roosevelt Blvd 30, Key West, United States View map

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Conch Republic Cottage

510 Petronia St, Key West, United States View map

During the stay at Conch Republic Cottage Key West, guests can indulge in windsurfing, snorkelling, and canoeing or visit Mel Fisher Maritime Heritage Museum, located 14 minutes' walk away. More

From US$ 952 Book Now

Tranquility On Ann Street

219 Ann Street #1, Key West, United States View map

The 1-bedroom Tranquility On Ann Street Villa Key West entices guests to enjoy windsurfing, snorkelling, and canoeing and offers proximity to Key West First Legal Rum Distillery, located just 8… More

From US$ 931 Book Now

The Beaming Barracuda By Last Key Realty

101 Front Street #9, Key West, United States View map

Located just a 5-minute stroll from Truman Little White House, the 3-bedroom The Beaming Barracuda By Last Key Realty Key West villa gives easy access to various tourist attractions in the area. More

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Parking Pool Dock - Starboard House

18 Andrea Lane, Key West, United States View map

Featuring a private swimming pool for guests' relaxation, the 9-bedroom Parking Pool Dock - Starboard House Villa Key West is located about 20 minutes' walk from Safe Harbor. Featuring access to a… More

From US$ 3814 Book Now

The Smiling Ibis By Last Key Realty

911 Windsor Lane, Key West, United States View map

Nestled in the vibrant heart of Key West, The Smiling Ibis By Last Key Realty offers guests a charming escape just 5 km from Key West International Airport. More

From US$ 1650 Book Now

Modern In The Meadows By Last Key Realty

1312 Pine Street, Key West, United States View map

Situated nearly 25 minutes' walk from Southernmost Point, the 5-bedroom Modern In The Meadows By Last Key Realty Key West villa offers a private swimming pool, a spa salon for guests to relax in. More

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Plantation Tropicale By Last Key Realty

1430 Tropical Street, Key West, United States View map

Plantation Tropicale By Last Key Realty Key West villa is located 25 minutes' walk from Saint Paul's Episcopal Church of Key West and provides a private swimming pool, ensuring a relaxing stay. More

From US$ 1619 Book Now

Emmas Secret By Avantstay Heart Of Old Town W Shared Pool Month Long Stays Only

717 A Emma Street, Key West, United States View map

**Emmas Secret is where charm meets modern luxury in the heart of Old Town. This exquisite retreat offers guests an unparalleled experience with its vibrant ambiance, lush landscapes, and a shared… More

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Casa Rosa

331 Simonton Street, Key West, United States View map

Casa Rosa Villa Key West is located only a 6-minute walk from the Papa's Pilar Rum Distillery and features a swimming pool and a patio for a relaxing stay. This property is situated within reach of… More

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Middle Sunset

801 Eisenhower Dr. #2, 2, Key West, United States View map

Middle Sunset Villa Key West is located a 5-minute walk from The Unitarian Universalist Fellowship of Key West, and offers tour/ticket assistance to provide an entertaining experience. More

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Oyster'S Pearl

620 Thomas Street #169, Key West, United States View map

Oyster'S Pearl Villa Key West offers proximity to such city sites as the San Carlos Institute, located only 6 minutes' walk away. More

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The Cozy Starfish By Last Key Realty

204 Southard Street #6, Key West, United States View map

**Discover the Charm of The Cozy Starfish By Last Key Realty** Nestled in the heart of Key West, The Cozy Starfish By Last Key Realty offers an unforgettable escape for travelers seeking relaxation… More

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Golden Nugget At Scarlet Mango Inn Key West

603 Southard St., Key West, United States View map

Located a mere 1.1 km from the Key West Butterfly and Nature Conservatory, Golden Nugget At Scarlet Mango Inn Key West is about a 5-minute walk from the Grinnell Caroline Street. Offering a heated… More

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Nautical Wheeler

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

Positioned just 10 kilometers from the vibrant atmosphere of Key West International, the Nautical Wheeler Villa Key West serves as an idyllic sanctuary for travelers seeking the perfect coastal… More

From US$ 2027 Book Now

Waterfront Luxury Home - Tidelands House

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

During the stay at Waterfront Luxury Home - Tidelands House Key West, guests can indulge in fisheries or visit Key West Tropical Forest and Botanical Garden, located a 25-minute walk away. More

From US$ 2333 Book Now

Southernmost Hospitality VII By Last Key Realty

1224 Duval St, Key West, United States View map

The 8-bedroom Southernmost Hospitality VII By Last Key Realty Key West villa offers proximity to such city sites as Key West Lighthouse and Keeper's Quarters Museum, located nearly 5 minutes' walk… More

From US$ 3730 Book Now

Louisa House

521 Louisa Street, Key West, United States View map

**Welcome to Louisa House Villa Key West,** a vibrant oasis nestled in the heart of Duval Street. This enchanting retreat offers an unrivaled blend of island-inspired charm and modern amenities… More

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Soleil Chalet

1116 Varela, Key West, United States View map

The 3-bedroom Soleil Chalet Key West is located around a 20-minute walk from Duval Street and provides windsurfing, snorkelling, and canoeing for active guests. More

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Sirens Serenade By Last Key Realty

66 Front Street, Key West, United States View map

Located 6 km from Fort East Martello Museum, Sirens Serenade By Last Key Realty Key West villa gives access to various tourist sites in the vicinity. More

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A Southard Pearl

202-11 Southard Street, Key West, United States View map

A Southard Pearl Villa Key West offers quick access to such city attractions as the US 1 Mile Marker 0, located just a 6-minute walk away. More

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Gypsyginny'S Hideaway

900 White Street #2, Key West, United States View map

The 2-bedroom Gypsyginny'S Hideaway Key West villa provides easy access to various city attractions, such as The Unitarian Universalist Fellowship of Key West, situated approximately a 5-minute walk… More

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Island Pearls

527 Fleming Street, Key West, United States View map

Situated a mere 6 minutes' stroll from 7 Artists & Friends Gallery, the 2-bedroom Island Pearls Villa Key West offers quick access to numerous city landmarks nearby. More

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A Key West State Of Mind

49 Spoonbill Way, Key West, United States View map

A Key West State Of Mind Villa Stock Island offers swift access to various city sites, such as FYT Fitness Center, situated nearly 5 minutes' walk away. More

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Banana Breeze

2863 Key Cove Dr., Key West, United States View map

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From US$ 1576 Book Now

Away From It All

620 Thomas St., #283, Key West, United States View map

Away From It All Key West villa offers easy access to such tourist spots as the US 1 Mile Marker 0, located just a 6-minute walk away. More

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Sailor'S Story

564 Porter Lane, Key West, United States View map

Situated only 6 minutes' walk from the San Carlos Institute, Sailor'S Story Villa Key West offers easy access to numerous tourist spots in the area. More

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Casa Oliviana By Last Key Realty

803 Olivia Street, Key West, United States View map

Staying at the 4-bedroom Casa Oliviana By Last Key Realty Key West, guests can visit Key West Cemetery, which is merely a 13-minute walk away. More

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Sand Crab Cabana Weekly Rental!

620 Thomas Street, #269, Key West, United States View map

Sand Crab Cabana Weekly Rental! Key West offers easy access to such tourist spots as the US 1 Mile Marker 0, located just a 6-minute walk away. More

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Windward Breeze

606 Truman Ave #7, Key West, United States View map

Located right in the centre of Key West, the 117 m² Windward Breeze Apartment Key West offers fast access to Fort Zachary Taylor about 20 minutes' walk away. Guests can make the most of their stay at… More

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Tropical Executive

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

Situated only 1.8 km from the Key West Butterfly and Nature Conservatory, Tropical Executive Villa Key West entices guests to explore various tourist attractions in the area. More

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Paradise Found

711 William Street, Key West, United States View map

The 2-bedroom Paradise Found Key West villa offers swift access to various city sites, such as Key West Lighthouse and Keeper's Quarters Museum, situated approximately 5 minutes' walk away. This… More

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Scott'S Cottage - Truman @ Duval Unit F

Truman Avenue, Key West, United States View map

The 1-room Scott'S Cottage - Truman @ Duval Unit F Key West is located in the Downtown Key West district of Key West, approximately 5 minutes' walk from the Ernest Hemingway Home and Museum. More

From US$ 363 Book Now