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2026-11-14
2026-11-15
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Hotels with indoor pool in Key West

Tom'S Oceanfront Penthouse

1800 Atlantic Blvd Unit A401, Key West, United States View map

Located approximately a 25-minute walk from the downtown commercial zoned Duval Street, the 3-bedroom Tom'S Oceanfront Penthouse Villa Key West has an outdoor swimming pool and is ideal for up to 8… More

From US$ 1057 Book Now

Awai'S Floating Villa - Houseboat In Luxury Village

Shrimp Road 7001, Key West, United States View map

**Experience Awai's Floating Villa - Houseboat In Luxury Village** Nestled in the serene heart of Key West, Awai's Floating Villa offers a unique escape on the tranquil waters of Luxury Village. More

From US$ 568 Book Now

Tropical Dreaming By Avantstay

607 Amelia St, Key West, United States View map

Nestled only a 12-minute walk from the San Carlos Institute, the welcoming Tropical Dreaming By Avantstay Key West villa features a swimming pool along with a patio to help guests unwind. Boasting… More

From US$ 2051 Book Now

Duval Street Suite With Pool

Duval Street 824, Key West, United States View map

The Duval Street Suite With Pool is a refined retreat located in the heart of Key West. Just 200 metres from the iconic Ernest Hemingway Home and Museum, this exquisite accommodation places you at… More

From US$ 323 Book Now

Amelia Home By Avantstay

605 Amelia Street, Key West, United States View map

Located around 10 minutes' walk from the downtown commercial zoned Duval Street, the 0-bedroom Amelia Home By Avantstay Key West boasts a swimming pool with a patio for additional relaxation. More

From US$ 903 Book Now

Jasmine Place

919 Whitehead Street, Key West, United States View map

During the stay at Jasmine Place Key West villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the 19 - acre Key West Cemetery, located a 13-minute walk away. More

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Beach House Condo By Avantstay

620 Thomas St, Key West, United States View map

If you want to stay in the Downtown Key West district, the 2-room Beach House Condo By Avantstay Key West is a good choice located, approximately a 15-minute walk from the Key West Butterfly and… More

From US$ 388 Book Now

Frost Free In Cayo Hueso

1800 Atlantic Blvd Unit C439, Key West, United States View map

Located just a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Frost Free In Cayo Hueso Villa is suitable for 6 guests and provides a swimming pool to relax in. The holiday home features… More

From US$ 696 Book Now

New The Altair House - Fire Pit Pool & Hot Tub

Mangrove Lane 13, Key West, United States View map

Featuring a private pool, the 6-bedroom New The Altair House - Fire Pit Pool & Hot Tub Villa Key West is suitable for up to 14 people and is located about a 15-minute walk from the Key West Tropical… More

From US$ 4188 Book Now

Ibis By Avantstay

714 Olivia #11, Key West, United States View map

Staying at the 0-bedroom Ibis By Avantstay Key West villa, guests can visit Mile Marker 0 Store, which is only 1 km away. More

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Oceanfront Oasis

1901 South Roosevelt Blvd, Unit 304, Key West, United States View map

The 2-bedroom Oceanfront Oasis Villa Key West entices guests to enjoy windsurfing, snorkelling, and canoeing and offers proximity to the Higgs Beach Dog Park, located approximately a 5-minute stroll… More

From US$ 550 Book Now

Anchor Drop Key West

1800 Atlantic Blvd, Unit A307, Key West, United States View map

During the stay at Anchor Drop Key West Villa, guests can indulge in windsurfing, snorkelling, and canoeing or visit the Higgs Beach, located a 19-minute walk away. The 2-bedroom holiday home offers… More

From US$ 870 Book Now

Latitude Penthouse Key West

1800 Atlantic Blvd Unit B417, Key West, United States View map

Featuring a Jacuzzi and a sauna, the 2-bedroom Latitude Penthouse Key West Villa is located only a 9-minute walk from the Higgs Beach Dog Park and can host up to 6 guests. The holiday home features… More

From US$ 685 Book Now

Andros Suite

921 Center Street #6, Key West, United States View map

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Aquaria House -Pool & Boat Dock

Shoreline Road 14, Key West, United States View map

Situated just 1.8 km from Safe Harbor, the 4-bedroom Aquaria House -Pool & Boat Dock Villa Key West features a patio with views of the sea. Offering a private swimming pool, this property invites… More

From US$ 3784 Book Now

Brisa Del Mar By Avantstay

1901 S.Roosevelt Blvd 206E, Key West, United States View map

The welcoming Brisa Del Mar By Avantstay Key West villa is located a 10-minute drive from the Key West Firehouse Museum and provides a swimming pool, ensuring a relaxing stay. More

From US$ 615 Book Now

Trumans Hideaway By Avantstay

113 Front St #108, Key West, United States View map

Featuring a swimming pool and a patio, the spacious Trumans Hideaway By Avantstay Key West apartment is situated in the Downtown Key West district, 800 metres from the Key West First Legal Rum… More

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Sweet Caroline

Caroline Street 537, Key West, United States View map

Sweet Caroline Villa Key West, situated right in the centre of Key West, and an 8-minute walk from the bustling plaza "Mallory Square", can accommodate up to 8 guests. Located a short way from the… More

From US$ 2148 Book Now

Charming Key West Rental

3 Coral Way, Key West, United States View map

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From US$ 680 Book Now

New! Villa Positano - Duval Square Condo, Pool, Hot Tub & Parking

Duval Street 1075, Key West, United States View map

**Welcome to Villa Positano - Duval Square Condo** Nestled in the vibrant heart of Duval, the Villa Positano presents an exquisite retreat blending contemporary elegance with a touch of coastal charm. More

From US$ 718 Book Now

The Fleming Suite

1501 Truman Avenue 3, Key West, United States View map

The Fleming Suite Key West villa is nestled a 9-minute walk from the Fleming Street and can accommodate up to 4 guests. More

From US$ 357 Book Now

The Elizabeth Suite

1501 Truman Avenue 1, Key West, United States View map

Offering access to entertainment venues such as the White Street Pier, situated only 1.5 km away, the 1-bedroom The Elizabeth Suite Key West villa can host up to 4 guests. More

From US$ 383 Book Now

New Coastal Rose - Bright Loft With High Ceilings

Rose Lane 526, Key West, United States View map

The spacious 84 m² New Coastal Rose - Bright Loft With High Ceilings Apartment Key West offers a central location nearly 5 minutes' walk from the Vandenberg Wreck. At the 1-bedroom apartment, guests… More

From US$ 858 Book Now

Curry House Room 6

Fleming Street 806, Key West, United States View map

Curry House: Your Gateway to Key West's Charm With popular attractions such as the Sails To Rails Museum and the stunning Florida Keys Beaches just a stone's throw away, Curry House Room 6 places you… More

From US$ 340 Book Now

Sunrise Suites Antigua Suite #312

Key West, United States View map

Sunrise Suites Antigua Suite #312 Key West is approximately a 25-minute walk from the Smathers Beach, giving access to numerous sites in the area. More

From US$ 166 Book Now

Always Your Paradise By Avantstay

620 Thomas Street #164, Key West, United States View map

Situated only 450 metres from the downtown commercial zoned Duval Street, the 1-bedroom Always Your Paradise By Avantstay Key West villa has a swimming pool with a patio. Featuring access to a patio,… More

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New Rose Petal Petite Suite - Pool & Parking

Rose Lane 526, Key West, United States View map

Featuring an outdoor swimming pool and a patio, the spacious 74 m² New Rose Petal Petite Suite - Pool & Parking Key West is situated in a historic area, just 1.3 km from the Key West Firehouse Museum… More

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Hemingways Atlantic Retreat

1800 Atlantic Blvd Unit C339, Key West, United States View map

Located 9 minutes' walk from the Higgs Beach Dog Park, Hemingways Atlantic Retreat Villa Key West is suitable for 6 guests and provides a sauna for a truly relaxing stay. The 2-bedroom holiday home… More

From US$ 404 Book Now

Sunrise Suites Big Kahuna Suite #202

Key West, United States View map

To enjoy your vacation in Key West, stay at Sunrise Suites Big Kahuna Suite #202 Key West, which is only 1.9 km from Sheriff s Animal Farm and about 20 minutes on foot from State Harbor. More

From US$ 339 Book Now

Brand New Catchlight House With Private Pool

Mangrove Lane 7, Key West, United States View map

Situated around a 25-minute walk from the Cozumel Park, the 6-bedroom Brand New Catchlight House With Private Pool Villa Key West invites guests to relax at a patio. Guests can enjoy fishing at this… More

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Upper Sunset North

801 Eisenhower Dr. #8, 8, Key West, United States View map

**Experience Laid-Back Luxury at Upper Sunset North Villa Key West** Recreational amenities abound, with a lavish outdoor pool surrounded by lounge chairs and tables for ultimate relaxation. More

From US$ 884 Book Now

Sugar Palm Suite At Travelers Palm Inn Key West

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

Located nearly 25 minutes' walk from the Harry S. Truman Little White House, the 1-bedroom Sugar Palm Suite At Travelers Palm Inn Key West villa has a swimming pool and is ideal for up to 4 guests. More

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Dolce Vita

7001 Shrimp Rd, Key West, United States View map

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From US$ 473 Book Now

The Curacao - Key West Condo With Pool, Balcony, Sunset Views

3625 Seaside Drive #204, Key West, United States View map

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Sun, Sea, And Sky

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

Situated only 7 minutes' walk from the downtown commercial zoned Duval Street, the 1-bedroom Sun, Sea, And Sky Villa Key West entices guests with snorkelling and fishing in the area. More

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Away From It All

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

Located just 6 minutes' walk from Mile Marker 0 Store, the 2-bedroom Away From It All Key West villa offers quick access to various city attractions in the vicinity. More

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Sublime Sunsets

107 Front St #214, Key West, United States View map

Located only a 9-minute walk from the natural history museum "Florida Keys Eco-Discovery Center", the 4-bedroom Sublime Sunsets Villa Key West features a swimming pool and can accommodate up to 8… More

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Byrd Nest By Avantstay

831 Georgia St, Key West, United States View map

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Saltwater Angler

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

At the 2-bedroom Saltwater Angler Villa Key West, guests can enjoy snorkelling and fishing as well as a location within easy reach of the Harry S. Truman Little White House. More

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Foster'S Folly

Snapper Lane, Key West, United States View map

Located 950 m from the National Key Deer Refuge, the 3-bedroom Foster'S Folly Villa Key West has a swimming pool and is ideal for up to 6 guests. More

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Amberjack

253 Southard Street, Key West, United States View map

Offering a location a mere 1.5 km from the Key West Butterfly and Nature Conservatory, the 2-bedroom Amberjack Villa Key West gives access to various tourist spots in the area. More

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Aqua Breeze

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

Featuring a swimming pool, the 2-bedroom Aqua Breeze Villa Key West is located approximately 5 minutes' walk from the fully accredited Mel Fisher Maritime Heritage Museum and is suitable for up to 5… More

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Sugar Palm Studio At Travelers Palm Inn Key West

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

Up to 2 guests can stay at the 1-bedroom Sugar Palm Studio At Travelers Palm Inn Key West villa and enjoy Saint Mary Star of the Sea Basilica, located approximately a 5-minute walk away. The property… More

From US$ 567 Book Now

Alhambra

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

Featuring a swimming pool, Alhambra Villa Key West is suitable for up to 4 people and is located a 15-minute walk from Southernmost Point of the Continental US Monument. More

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

Truman Avenue 417, Key West, United States View map

The 5-bedroom Bachelorparty Hq For 16-Feet To Duval-Pool-Hot Tub Villa Key West accommodates up to 16 guests and offers proximity to the South Beach, located only 9 minutes' walk away. More

From US$ 1984 Book Now

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

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

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Royal Poinciana Weekly Rental!

620 Thomas Street #292, Key West, United States View map

During the stay at Royal Poinciana Weekly Rental! Key West villa, guests can indulge in snorkelling and fishing or visit the waterfront Mallory Square, located a 14-minute walk away. More

From US$ 428 Book Now

Seascape

620 Thomas Street #159, Key West, United States View map

The 2-bedroom Seascape Villa Key West hosts up to 4 guests and provides proximity to the Ernest Hemingway Home and Museum, situated merely 0.6 km away. More

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The Lighthouse Penthouse Suite

419 Truman Avenue, Key West, United States View map

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Lighthouse Suites Collection

419 Truman Avenue, Key West, United States View map

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