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2026-11-09
2026-11-10
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Holiday Homes in Key West

Seagate House -Waterfront W Dock

Shoreline Road 10, Key West, United States Show map

Seagate House -Waterfront W Dock Villa Key West is located a 25-minute walk from Key West Golf Club and provides a swimming pool, ensuring a relaxing stay. The 4-bedroom villa hosts up to 10 guests… More

From US$ 2225 Book Now

The Ebberly House - Amazing Pool In Gated Community

Shoreline Road 1, Key West, United States Show map

Featuring an outdoor swimming pool, The Ebberly House - Amazing Pool In Gated Community Villa Key West is located 6 minutes' walk from FYT Fitness Center and is suitable for up to 14 guests. Located… More

From US$ 4783 Book Now

Margaret Street Retreat

628 Margaret St, Key West, United States Show map

Situated about a 5-minute walk from Key West Historic Seaport, Margaret Street Retreat Villa Key West provides access to numerous tourist attractions in the area. More

From US$ 615 Book Now

Banana Breeze

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

The 4-bedroom Banana Breeze Villa Key West is situated a mere 6 minutes on foot from Dive Key West and offers guests to relax with a Jacuzzi. This accommodation is 2.6 km from Key West Firehouse… More

From US$ 1576 Book Now

Away From It All

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

Offering an outdoor swimming pool, the 2-bedroom Away From It All Key West villa is located merely 9 minutes' walk from the natural history museum "Florida Keys Eco-Discovery Center" and is ideal for… More

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Upper Bayview North

801 Eisenhower Dr. #7, 7, Key West, United States Show map

The 4-bedroom Upper Bayview North Villa Key West is located just 0.7 km from Fleming Street and features a heated pool as well as a terrace for guests' pleasure. Offering an ATM and a lift, this Key… More

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Sailor'S Story

564 Porter Lane, Key West, United States Show map

The 2-bedroom Sailor'S Story Villa Key West, located a mere 6 minutes' walk from San Carlos Institute, can host up to 4 guests. The holiday home features opportunities for snorkelling and fisheries… More

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Shang Ri La By Last Key Realty

1800 Atlantic Blvd #A306, Key West, United States Show map

Shang Ri La By Last Key Realty Key West villa with a convenient location a 7-minute walk from White Street Pier entices guests with a Jacuzzi. Located 3.2 km from the waterfront Mallory Square, the 2… More

From US$ 466 Book Now

Waterfront Estate In Shark Key

87 Cannon Royal Drive, Key West, United States Show map

The 5-bedroom Waterfront Estate In Shark Key Villa Key West is located merely 1.9 km from Big Coppitt Key Island, giving access to various tourist spots nearby. This Key West holiday home is suitable… More

From US$ 875 Book Now

Lazy Gecko By Avantstay

817 Eaton Street #2, Key West, United States Show map

Up to 4 guests can stay at the welcoming Lazy Gecko By Avantstay Key West villa and enjoy Turtle Cannery Maritime Museum, located 350 metres away. More

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Bahama Gardens - Turtle House

714 Thomas Street, Key West, United States Show map

The 2-bedroom Bahama Gardens - Turtle House Villa Key West is located approximately 5 minutes' walk from The Ernest Hemingway Home and Museum and offers guests to relish a terrace as well as a year… More

From US$ 1053 Book Now

Casa Oliviana By Last Key Realty

803 Olivia Street, Key West, United States Show map

Located just a 7-minute walk from the downtown commercial zoned Duval Street, the 6-bedroom Casa Oliviana By Last Key Realty Key West features a swimming pool and can accommodate up to 12 guests. More

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Atlantic Cabana - Monthly Rental

1304 Atlantic Drive, Key West, United States Show map

Offering access to entertainment venues such as the arts theater "Red Barn Theatre", situated about a 25-minute walk away, the 3-bedroom Atlantic Cabana - Monthly Rental Key West can host up to 6… More

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Catch Of The Day

113 Front Street #106, Key West, United States Show map

The 3-bedroom Catch Of The Day Villa Key West entices guests to enjoy snorkelling and fisheries and offers proximity to the bustling plaza "Mallory Square", located only 9 minutes' stroll away. The… More

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Watson House Grand Estate

525 Simonton Street, Key West, United States Show map

The 11-bedroom Watson House Grand Estate Villa Key West accommodates up to 22 guests and offers proximity to Key West Historic Seaport, located merely a 5-minute walk away. This Key West villa… More

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Casa De Rosalie By Avantstay

1419 Truman Avenue, Key West, United States Show map

The 3-bedroom Casa De Rosalie By Avantstay Key West is situated only 1.6 km from The Ernest Hemingway Home and Museum and features an outdoor swimming pool with a patio. Staying at the Key West villa… More

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Casa Riviera Waterfront Hacienda With Pool And Boat Lift

3210 Riviera Drive, Key West, United States Show map

During the stay at the 3-bedroom Casa Riviera Waterfront Hacienda With Pool And Boat Lift Villa Key West, guests can indulge in a hot tub or visit Fort East Martello Museum, located 3.4 km away. This… More

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Life In The Slow Lane

101 Front Street #10, Key West, United States Show map

During the stay at Life In The Slow Lane Key West villa, guests can indulge in snorkelling and fisheries or visit the historical Key West Lighthouse, located a 13-minute walk away. Located within 400… More

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Best Time

210-8 Southard Street, Key West, United States Show map

Located merely an 8-minute walk from The Ernest Hemingway Home and Museum, the 2-bedroom Best Time Key West villa is suitable for 4 guests and provides an outdoor swimming pool to relax in. The… More

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Havana Mango Compound

2851 Key Cove Dr., Key West, United States Show map

Featuring a heated pool, the 8-bedroom Havana Mango Compound Key West villa is suitable for up to 16 people and is located about 10 minutes' drive from the downtown commercial zoned Duval Street. More

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Kw121Flr Casa Hueso

1321 Whitehead Street, Key West, United States Show map

Featuring a heated pool, Kw121Flr Casa Hueso Villa Key West is suitable for up to 8 people and is located a 17-minute walk from Nancy Forrester's Secret Garden. This 4-bedroom villa features… More

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Osprey Colony

714 Olivia St, Key West, United States Show map

At Osprey Colony Villa Key West, guests can enjoy windsurfing, snorkelling, and canyoning as well as a location just 7 minutes' walk from Key West Butterfly and Nature Conservatory. Located right… More

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Kw33A Leeward Isle

529 Olivia St, Key West, United States Show map

Nestled in the Duval district of Key West, the 2-bedroom Kw33A Leeward Isle Villa Key West is approximately 25 minutes' walk from Higgs Beach Dog Park and offers a Jacuzzi. The accommodation is… More

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World'S End

109 Front Street #113, Key West, United States Show map

Situated about 5 minutes' walk from USCGC Ingham Maritime Museum, the 2-bedroom World'S End Villa Key West is ideal for up to 4 guests. The holiday home boasts an aqua park and a golf course, while… More

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Envy Of The Island By Last Key Realty

317 Angela Street, Key West, United States Show map

Up to 10 guests can stay at the 5-bedroom Envy Of The Island By Last Key Realty Key West villa and enjoy Southernmost Point of the Continental US Monument, located just a 6-minute walk away. More

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Casa Caribe

506 Catherine St, Key West, United States Show map

Casa Caribe Villa Key West, located just a few steps from Key West Lighthouse and Keeper's Quarters Museum, can host up to 8 guests. The villa features opportunities for windsurfing, snorkelling, and… More

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Bahamian Reed By Avantstay

510 Porter Lane, Key West, United States Show map

Located in the Downtown Key West district, a 6-minute walk from San Carlos Institute, the welcoming Bahamian Reed By Avantstay Key West villa offers pool views. Providing guests with Wi-Fi and… More

From US$ 627 Book Now

3 4 Tim E

2853 Key Cove Dr., Key West, United States Show map

The 4-bedroom 3 4 Tim E Villa Key West is nestled a mere 450 metres from Kelly's Aerial Arts & Fitness and provides a hot tub. Offering a heated pool, the holiday home invites guests to visit Key… More

From US$ 2126 Book Now

A Peace Of Paradise

106-2 Southard Street, Key West, United States Show map

The 1-bedroom A Peace Of Paradise Key West villa is located within 25 minutes' walk of the vintage parish "Saint Paul's Episcopal Church of Key West", giving access to various tourist spots nearby. More

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Mermaid Cove

1219 Duval Street, Key West, United States Show map

Located approximately a 10-minute walk from San Carlos Institute, Mermaid Cove Key West villa provides access to various tourist attractions in the vicinity. More

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Chagall'S Corner

1016 Howe St #14, Key West, United States Show map

Situated right around the corner from Key West Lighthouse and Keeper's Quarters Museum, the 1-bedroom Chagall'S Corner Key West villa offers quick access to numerous city landmarks nearby. This Key… More

From US$ 578 Book Now

Kw378Flr Periwinkle Place

604 Truman Ave, Key West, United States Show map

The 1-bedroom Kw378Flr Periwinkle Place Key West villa, located just 5 minutes' walk from the historic Key West Lighthouse, can host up to 4 guests. This property features opportunities for… More

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The St Martin -Hot Tub & Pool

Seaside Drive 3625, Key West, United States Show map

Located about a 10-minute ride from Southernmost Point of the Continental US Monument, The St Martin -Hot Tub & Pool Villa Key West provides access to various tourist attractions in the vicinity. More

From US$ 435 Book Now

Sea Breeze Villa

1219 Grinnell Street Unit B, Key West, United States Show map

Situated just 8 minutes' walk from Higgs Beach, the 2-bedroom Sea Breeze Villa Key West is ideal for up to 6 guests. Located within a few blocks of Southernmost Point of the Continental US Monument… More

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Island Inspiration By Last Key Realty

1219 Margaret Street, Key West, United States Show map

Offering a location nearly 25 minutes' walk from Memorial Sculpture Garden, the 3-bedroom Island Inspiration By Last Key Realty Key West villa gives access to various tourist spots in the area. This… More

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Elizabeth'S Secret - Old Town Key West

910 Elizabeth St, Key West, United States Show map

Nestled an 18-minute walk from Papa's Pilar Rum Distillery, Elizabeth'S Secret - Old Town Key West Villa entices guests to explore various tourist destinations nearby. More

From US$ 1566 Book Now

Alhambra

620 Thomas Street #170, Key West, United States Show map

Up to 4 guests can stay at the 1-bedroom Alhambra Villa Key West and enjoy Mile Marker 0 Store, located just a 6-minute walk away. Providing guests with Wi-Fi and private parking, the holiday home is… More

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Haven House By Brightwild - Luxury Waterfront

Floral Avenue 8, Key West, United States Show map

Located just 500 metres from FYT Fitness Center, Haven House By Brightwild - Luxury Waterfront Villa Key West provides access to various tourist attractions in the vicinity. More

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Magical Ocean Penthouse

1800 Atlantic Blvd, C426, Key West, United States Show map

Welcoming guests with a Jacuzzi and a sauna, the 2-bedroom Magical Ocean Penthouse Villa Key West is located merely 9 minutes' walk from Higgs Beach Dog Park and can host up to 6 guests. The holiday… More

From US$ 702 Book Now

Conch Easy Livin'

617 Simonton Street, Key West, United States Show map

Situated in the Duval district of Key West, within 15 minutes' walk of Saint Mary Star of the Sea Basilica, the 2-bedroom Conch Easy Livin' Villa Key West comes with a heated pool for guests to… More

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Havana Views

620 Thomas Street #268, Key West, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Havana Views Key West villa is located only 8 minutes' walk from The Ernest Hemingway Home and Museum and is ideal for up to 4 guests. Providing… More

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Luxury Retreat-Old Town; Pool, Parking, Near Duval

921 Windsor Lane, Key West, United States Show map

Overlooking the pool, Luxury Retreat-Old Town; Pool, Parking, Near Duval Villa Key West enjoys a prime setting 5 minutes' walk from Key West Firehouse Museum. More

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Casa Avila By Last Key Realty

625 Eaton Street, Key West, United States Show map

The 3-bedroom Casa Avila By Last Key Realty Key West is located nearly a 25-minute walk from White Street Pier and provides a swimming pool, ensuring a relaxing stay. Offering a prime location in the… More

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Boat House By Avantstay

711 Bakers Lane, Key West, United States Show map

Located merely 6 minutes' walk from the downtown commercial zoned Duval Street, Boat House By Avantstay Key West villa features an outdoor swimming pool and can accommodate up to 2 guests. This 1… More

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Caroline On My Mind

616 Caroline St #4, Key West, United States Show map

Offering a heated pool, the 2-bedroom Caroline On My Mind Villa Key West is located around 5 minutes' walk from Vandenberg Wreck and is ideal for up to 4 guests. This property features opportunities… More

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Monkey House By Avantstay

709 Bakers Lane, Key West, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Monkey House By Avantstay Key West villa is located merely 0.6 km from Key West First Legal Rum Distillery and is ideal for up to 4 guests. Providing… More

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Shady Nook

620 Thomas Street, #149, Key West, United States Show map

Featuring an outdoor swimming pool, the 2-bedroom Shady Nook Villa Key West is located about 5 minutes' walk from Mile Marker 0 Store and is suitable for up to 4 guests. Providing guests with Wi-Fi… More

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11 Cottage Close To Duval St

709 Emma Street #3, Key West, United States Show map

11 Cottage Close To Duval St Key West is nestled a 6-minute walk from the downtown commercial zoned Duval Street and can accommodate up to 4 guests. Offering private parking as well as Wi-Fi, the 1… More

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Rooster Doodle Do - Midtown Family Retreat

2314 Patterson Ave, Key West, United States Show map

Situated approximately a 25-minute walk from Key West Butterfly and Nature Conservatory, Rooster Doodle Do - Midtown Family Retreat Villa Key West is suitable for 10 guests and provides a swimming… More

From US$ 311 Book Now

The Ibis & The Crane By Last Key Realty

909-911 Windsor Lane, Key West, United States Show map

Located 6 minutes' walk from Southernmost Point of the Continental US Monument, The Ibis & The Crane By Last Key Realty Key West villa is suitable for 16 guests and provides a heated pool to relax in… More

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