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

Banana Blossoms By Last Key Realty

407B Emma Street, Key West, United States Show map

Situated in the Downtown Key West district of Key West, around 15 minutes' walk from Fort Zachary Taylor, the 2-bedroom Banana Blossoms By Last Key Realty Key West villa comes with a swimming pool… More

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Saltwater Angler

115 Front Street #203, Key West, United States Show map

Providing guests with an aqua park and a golf course to ensure a memorable stay, the 2-bedroom Saltwater Angler Villa Key West is merely a 9-minute walk from the waterfront Mallory Square. Located in… More

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Mansion The Watson House

525 Simonton Street, Key West, United States Show map

Located only 8 minutes on foot from Key West First Legal Rum Distillery, the 7-bedroom Mansion The Watson House Villa Key West provides a swimming pool as well as windsurfing, snorkelling, and… More

From US$ 3310 Book Now

Kw322Flr Color Of The Keys

1901 S. Roosevelt Blvd #204E, Key West, United States Show map

Offering guests to unwind in a hot tub and a sauna, Kw322Flr Color Of The Keys Villa Key West is located 18 minutes' walk from White Street Pier. Guests can enjoy windsurfing, snorkelling, and diving… More

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Charmayne'S Cottages - Truman @ Duval

423 Truman Avenue, Key West, United States Show map

Staying at the 7-bedroom Charmayne'S Cottages - Truman @ Duval Key West, guests can easily reach the Harry S. Truman Little White House, located just 1.3 km away. The Key West villa is suitable for… More

From US$ 2492 Book Now

Tropical Village

708 South St & 1400 Alberta St, Key West, United States Show map

Located only an 8-minute stroll from Higgs Beach, the 12-bedroom Tropical Village Key West villa provides a heated pool as well as windsurfing, snorkelling, and canyoning to diversify guests' leisure… More

From US$ 4324 Book Now

Heron House | Canal Front Home W/ Private Dock!

12 Bamboo Terrace, Key West, United States Show map

Staying at the 3-bedroom Heron House | Canal Front Home W/ Private Dock! Key West, guests can easily reach Cozumel Park, located approximately a 25-minute walk away. This Key West holiday home is… More

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Lennons Lodge Luxury 2 Bedroom Private Spa 2 Heated Pools

918 Center Street, Key West, United States Show map

Lennons Lodge Luxury 2 Bedroom Private Spa 2 Heated Pools Key West enjoys a prime location, a 25-minute walk from White Street Pier, and offers guests to unwind in a Jacuzzi. Offering a car park as… More

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Casa Victoria By Last Key Realty

806 Truman Ave, Key West, United States Show map

The 5-bedroom Casa Victoria By Last Key Realty Key West, located within 10 minutes' walk of The Ernest Hemingway Home and Museum, invites guests to relax in a Jacuzzi. Offering a prime location in… More

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Brisa Fresca By Last Key Realty

509 Noah Lane, Key West, United States Show map

Located only a 7-minute walk from Fort Zachary Taylor, the 3-bedroom Brisa Fresca By Last Key Realty Key West villa offers a heated pool for guests to relax by. Located 2.4 km from Higgs Beach Dog… More

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Oyster'S Pearl

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

The 1-bedroom Oyster'S Pearl Villa Key West is nestled only a 6-minute walk from the downtown commercial zoned Duval Street and can accommodate up to 2 guests. Located in proximity to Southernmost… More

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Ocean View

1800 Atlantic Blvd, Unit C226, Key West, United States Show map

Featuring a sauna, the 2-bedroom Ocean View Villa Key West is located only 5 minutes' walk from Higgs Beach Dog Park and can host up to 6 guests. This 2-bathroom villa features opportunities for… More

From US$ 615 Book Now

A Sunset Poolside

620 Thomas Street #156, Key West, United States Show map

Located merely a 6-minute walk from the downtown commercial zoned Duval Street, A Sunset Poolside Villa Key West features an outdoor swimming pool and can accommodate up to 4 guests. Located right… More

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The Grinnell Cottage By Avantstay

611 Grinnell St, Key West, United States Show map

Offering an outdoor swimming pool, the 2-bedroom The Grinnell Cottage By Avantstay Key West is located nearly a 5-minute walk from the 19-acre Key West Cemetery and is ideal for up to 4 guests. More

From US$ 217 Book Now

After Hours @ Speakeasy Inn Key West!

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

Along with proximity to The Ernest Hemingway Home and Museum, merely a 6-minute stroll away, the 1-bedroom After Hours @ Speakeasy Inn Key West! villa offers opportunities for snorkelling and… More

From US$ 344 Book Now

Southern Skies, Stylish Home In Old Town Key West

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

Situated just 6 minutes on foot from Southernmost Point of the Continental US Monument, Southern Skies, Stylish Home In Old Town Key West is suitable for 6 guests and provides a swimming pool to… More

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Sugar Palm Studio At Travelers Palm Inn Key West

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

Situated merely a 9-minute walk from Key West Butterfly and Nature Conservatory, Sugar Palm Studio At Travelers Palm Inn Key West villa offers guests to relax by an outdoor swimming pool. This 1… More

From US$ 567 Book Now

Joan'S Caribbean Hideaway

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

Offering access to entertainment venues such as Key West Golf Club, situated only 1.4 km away, the 2-bedroom Joan'S Caribbean Hideaway Villa Key West can host up to 4 guests. The Key West holiday… More

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Shipyard 155

620 Thomas Unit 155, Key West, United States Show map

Featuring a swimming pool, the 2-bedroom Shipyard 155 Villa Key West is located just 6 minutes' walk from San Carlos Institute and is suitable for up to 4 guests. Providing guests with Wi-Fi and a… More

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The Toasted Coconut By Last Key Realty

423 Simonton Street, Key West, United States Show map

Situated nearly a 5-minute stroll from Key West Historic Seaport, the 3-bedroom The Toasted Coconut By Last Key Realty Key West villa is suitable for 8 guests and provides a swimming pool to relax in… More

From US$ 798 Book Now

La Casita By Avantstay

819 Terry Lane, Key West, United States Show map

The welcoming La Casita By Avantstay Key West villa hosts up to 4 guests and provides proximity to the downtown commercial zoned Duval Street, situated about a 5-minute walk away. More

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Harrisons Hideaway K Suite Private Spa

918 Center Street, Key West, United States Show map

Harrisons Hideaway K Suite Private Spa Key West villa with a prime location 400 metres from the downtown commercial zoned Duval Street entices guests with a Jacuzzi. Offering a car park as well as Wi… More

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Dune Wind South By Avantstay

1901 S.Roosevelt Blvd 201S, Key West, United States Show map

Featuring an outdoor swimming pool, the 2-bedroom Dune Wind South: Beachside Extended Stay with Pool & Hot Tub Key West villa is suitable for up to 4 people and is located about a 25-minute walk from… More

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Blue Horizon Hideaway

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

Situated just 6 minutes' stroll from Kelly's Aerial Arts & Fitness, the 2-bedroom Blue Horizon Hideaway Villa Key West offers quick access to numerous city landmarks nearby. More

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Kokomo Keys - Waterfront & Heated Pool

16725 Tamarind Road, Key West, United States Show map

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Southern Comfort

2855 Key Cove Dr., Key West, United States Show map

The 4-bedroom Southern Comfort Key West villa is situated approximately 500 metres from Kelly's Aerial Arts & Fitness and offers guests to relax with a Jacuzzi. Featuring access to a terrace, the… More

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Kw49B Papa

309 Louisa St. #2, Key West, United States Show map

Situated in the Downtown Key West district of Key West, just 1.4 km from Nancy Forrester's Secret Garden, the 1-bedroom Kw49B Papa Villa Key West comes with a swimming pool for guests to unwind. More

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Reynolds Retreat

1308 Reynolds Street, Key West, United States Show map

Located just 11 minutes' walk from the historic Saint Mary Star of the Sea Church, the 3-bedroom Reynolds Retreat Villa Key West gives access to various tourist sites in the vicinity. More

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Dolphin Watch

100-1 Eaton Street, Key West, United States Show map

Dolphin Watch Villa Key West boasts an aqua park and a golf course and enjoys its location in the Downtown Key West district, 6 minutes' walk from Audubon House and Tropical Gardens. Located 2.1 km… More

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Wk49D Papa

309 Louisa St #4, Key West, United States Show map

Featuring guided snorkelling trips to make your visit more entertaining, Wk49D Papa Key West villa is a 16-minute walk from USCGC Ingham Maritime Museum. Guests can enjoy snorkelling and diving at… More

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Old Town Main House Guest House Close To Duval

614 Virginia Street, Key West, United States Show map

Staying at the 2-bedroom Old Town Main House Guest House Close To Duval Key West villa, guests can visit US 1 Mile Marker 0, which is just 0.8 km away. More

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The Artists Muse By Last Key Realty

712 Love Lane, Key West, United States Show map

Situated around a 5-minute stroll from Key West Historic Seaport, the 4-bedroom The Artists Muse By Last Key Realty Key West villa is suitable for 8 guests and provides a heated pool to relax in. More

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Southernmost Retreat

1124 Duval Street, Key West, United States Show map

Situated a few steps from Key West Lighthouse and Keeper's Quarters Museum, the 4-bedroom Southernmost Retreat Key West villa is ideal for up to 12 guests. More

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Swept Away By Last Key Realty

1213 Margaret Street, Key West, United States Show map

Located 0.6 km from Higgs Beach, Swept Away By Last Key Realty Key West villa is suitable for 4 guests and provides a swimming pool to relax in. More

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Another Three Hour Tour

620 Thomas Street #153, Key West, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Another Three Hour Tour Key West villa is located just 7 minutes' walk from the downtown commercial zoned Duval Street and is ideal for up to 4 guests… More

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Foster'S Folly

Snapper Lane, Key West, United States Show map

Featuring a heated pool, the 3-bedroom Foster'S Folly Villa Key West is suitable for up to 6 people and is located 4.3 km from National Key Deer Refuge Visitor Center. Providing guests with Wi-Fi and… More

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Suncoast House -Pool & Boat Dock

Shoreline Road 12, Key West, United States Show map

Situated just 1.3 km from Key Haven, the 5-bedroom Suncoast House -Pool & Boat Dock Villa Key West provides fitness classes, as well as a fitness room for active guests. Offering a swimming pool… More

From US$ 1786 Book Now

Paradise Found In The Center Of Old Town

907 Center St, Key West, Fl 33040, Key West, United States Show map

Paradise Found In The Center Of Old Town Key West villa is located an 8-minute walk from Key West Butterfly and Nature Conservatory and offers guests to enjoy diving, canyoning, and hiking. Nestled… More

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A Sunrise Cottage

204-1 Southard Street, Key West, United States Show map

Featuring an outdoor swimming pool, the 2-bedroom A Sunrise Cottage Key West is located merely 6 minutes' walk from Mile Marker 0 Store and is suitable for up to 6 guests. Providing guests with Wi-Fi… More

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Kw242Flr Petronia Paradise

1121 Petronia St, Key West, United States Show map

Featuring horse riding tours to make your visit more entertaining, Kw242Flr Petronia Paradise Key West villa is a 25-minute walk from Fort Zachary Taylor. Guests can enjoy snorkelling, diving, and… More

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Kw31C Jasmine Suite

521 Simonton St. #2, Key West, United States Show map

The 1-bedroom Kw31C Jasmine Suite Key West villa accommodates up to 4 guests and offers proximity to the downtown commercial zoned Duval Street, located merely 5 minutes' walk away. This Key West… More

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Dos Casitas By Last Key Realty

512 Catherine #2 & 516 Catherine Street, Key West, United States Show map

Located merely 550 metres from The Ernest Hemingway Home and Museum, the 5-bedroom Dos Casitas By Last Key Realty Key West villa provides a heated pool, a Jacuzzi for a more relaxing experience. More

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Driftwood Dreams By Last Key Realty

1800 Atlantic Blvd #C323, Key West, United States Show map

Located about a 5-minute walk from Higgs Beach Dog Park, the 2-bedroom Driftwood Dreams By Last Key Realty Key West villa boasts a heated pool and can accommodate up to 6. Providing guests with Wi-Fi… More

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A Southard Pearl

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

Offering an outdoor swimming pool, the 1-bedroom A Southard Pearl Villa Key West is located just 8 minutes' walk from The Ernest Hemingway Home and Museum and is ideal for up to 2 guests. Located… More

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Spirit Of Key West By Last Key Realty

1106 Petronia Street, Key West, United States Show map

The 4-bedroom Spirit Of Key West By Last Key Realty villa hosts up to 8 guests and provides proximity to Fleming Street, situated a mere 0.7 km away. Providing guests with Wi-Fi and private parking… More

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Poolside Hangover

620 Thomas Street #287, Key West, United States Show map

Up to 6 guests can stay at the 2-bedroom Poolside Hangover Key West villa and enjoy Mile Marker 0 Store, located merely a 6-minute walk away. Providing guests with Wi-Fi and private car parking, this… More

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Colony Poolside

714 Olivia Street, Key West, United States Show map

Located just 500 metres from Southernmost Point of the Continental US Monument, the 1-bedroom Colony Poolside Villa Key West offers opportunities for windsurfing, snorkelling, and canyoning in the… More

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Southernmost Hospitality V By Last Key Realty

1224 Duval St, Key West, United States Show map

The 5-bedroom Southernmost Hospitality V By Last Key Realty Key West villa provides easy access to various city attractions, such as Southernmost Point of the Continental US Monument, situated merely… More

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Mother Ocean

2857 Key Cove Dr., Key West, United States Show map

The 4-bedroom Mother Ocean Key West villa, located merely a 6-minute walk from Kelly's Aerial Arts & Fitness, can host up to 8 guests. This property features opportunities for snorkelling and… More

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Conch Paradise

1800 Atlantic Blvd #B316, Key West, United States Show map

Situated a mere 9 minutes' walk from Higgs Beach Dog Park, the 2-bedroom Conch Paradise Key West villa offers a sauna and can accommodate up to 6 guests. This property features opportunities for… More

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