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2026-11-05
2026-11-06
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Hotels with indoor pool in Key West

Shady Palms

1415 Petronia Street, Key West, United States Show map

The 2-bedroom Shady Palms Villa Key West entices guests to enjoy snorkelling, canyoning, and fisheries and offers proximity to Fleming Street, located just 9 minutes' stroll away. Featuring a terrace… More

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Forever Young

115 Front Street, #202, Key West, United States Show map

The 2-bedroom Forever Young Key West villa is situated nearly 5 minutes' walk from Front Street, featuring such comforts as Wi-Fi and a private parking lot. Offering a prime location in the Downtown… More

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Linger Longer By Avantstay

277 Southard Street, Key West, United States Show map

Situated in the Downtown Key West district of Key West, nearly 20 minutes' walk from Bayview Park, the 2-bedroom Linger Longer By Avantstay Key West villa comes with an outdoor swimming pool for… More

From US$ 400 Book Now

Sunset South

801 Eisenhower Dr. #1, 1, Key West, United States Show map

Featuring a heated pool, Sunset South Villa Key West is suitable for up to 4 people and is located 18 minutes' walk from the downtown commercial zoned Duval Street. Providing guests with Wi-Fi and a… More

From US$ 474 Book Now

A Fish Bowl Too

620 Thomas Street #157, Key West, United States Show map

A Fish Bowl Too Villa Key West is located a 16-minute walk from Fort Zachary Taylor and provides snorkelling and fisheries for active guests. Located in the vicinity of the performing arts theater… More

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Royal Palm Studio At Travelers Palm Inn Key West

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

Situated a mere 9 minutes' walk from the very unusual Key West Cemetery, the 1-bedroom Royal Palm Studio At Travelers Palm Inn Key West villa is ideal for up to 2 guests. This accommodation features… More

From US$ 390 Book Now

Isle Be Back

620 Thomas Street, #281, Key West, United States Show map

Offering an outdoor swimming pool, the 2-bedroom Isle Be Back Villa Key West is located nearly a 5-minute walk from The Ernest Hemingway Home and Museum and is ideal for up to 4 guests. Located… More

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Bananas Foster Guesthouse

Caroline Street 537, Key West, United States Show map

Located in Duval with unique, island inspired Small Plates with bold Caribbean spices and fresh local seafood, a 6-minute walk from Nancy Forrester's Secret Garden, the spacious Bananas Foster… More

From US$ 3573 Book Now

Three Duval Street Suites W Parking And Pool

824 Duval Street, Key West, United States Show map

Located around 5 minutes' walk from the downtown commercial zoned Duval Street, the 3-bedroom Three Duval Street Suites W Parking And Pool Key West villa offers a swimming pool for guests to relax by… More

From US$ 2562 Book Now

A Sunset And Harbour View

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

Featuring an outdoor swimming pool, the 2-bedroom A Sunset And Harbour View Villa Key West is located merely 6 minutes' walk from Key West Shipwreck Treasure Museum and is suitable for up to 6 guests… More

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A Bird'S Eye View

102-7 Southard Street, Key West, United States Show map

The 2-bedroom A Bird'S Eye View Villa Key West entices guests to enjoy snorkelling and fisheries and offers proximity to The Ernest Hemingway Home and Museum, located just 9 minutes' stroll away. More

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Carysfort Reef Light Suite

419 Truman Avenue, Key West, United States Show map

Situated around 5 minutes on foot from The Ernest Hemingway Home and Museum, the 2-bedroom Carysfort Reef Light Suite Key West villa is suitable for 6 guests and provides a swimming pool to relax in.… More

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Island Time

202-6 Southard Street, Key West, United States Show map

Situated a mere 8 minutes' stroll from the Harry S. Truman Little White House, the 2-bedroom Island Time Villa Key West is suitable for 4 guests and provides an outdoor swimming pool to relax in. More

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Sublime Sunsets

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

During the stay at Sublime Sunsets Villa Key West, guests can indulge in snorkelling and fisheries or visit Key West Butterfly and Nature Conservatory, located a 25-minute walk away. Offering a… More

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Elegant Waterfront Corner Residence

5601 College Road, Unit A102, Key West, United States Show map

Situated 6 km from the downtown commercial zoned Duval Street, Elegant Waterfront Corner Residence Key West offers a hot tub and a sauna for 6 visitors. This apartment features high-speed Internet… More

From US$ 435 Book Now

Sunset North

801 Eisenhower Dr. #3, 3, Key West, United States Show map

Featuring an outdoor swimming pool as well as views of the city, Sunset North Villa Key West offers a prime location 9 minutes' walk from Fleming Street. Guests of the 4-bedroom holiday home, located… More

From US$ 1501 Book Now

Upper Sunset South

801 Eisenhower Dr. #9, 9, Key West, United States Show map

During the stay at Upper Sunset South Villa Key West, guests can indulge in snorkelling and fisheries or visit Key West First Legal Rum Distillery, located 25 minutes' walk away. Located 1.8 km from… More

From US$ 951 Book Now

Afternoon Delight

401 Emma Street Apt F, Key West, United States Show map

During the stay at Afternoon Delight Villa Key West, guests can indulge in snorkelling and fisheries or visit Fort Zachary Taylor, located a 15-minute walk away. Offering private parking as well as… More

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Island Breezes Weekly Rental

620 Thomas Street #271, Key West, United States Show map

Located just a 6-minute walk from the downtown commercial zoned Duval Street, the 2-bedroom Island Breezes Weekly Rental Key West villa features a heated pool and can accommodate up to 4 guests. More

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Kw49C Papa

309 Louisa St. #3, Key West, United States Show map

Situated in the Downtown Key West district of Key West, nearly 25 minutes' walk from C. B. Harvey Rest Beach Park, the 1-bedroom Kw49C Papa'S Hideaway #3 - For Whom The Bell Tolls Villa Key West… More

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Middle Sunset

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

Located just 1.6 km from Nancy Forrester's Secret Garden, the 3-bedroom Middle Sunset Villa Key West has an outdoor swimming pool and is ideal for up to 6 guests. Along with an ATM machine and a lift… More

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Kw49A Papa

309 Louisa St #1, Key West, United States Show map

Situated in the Downtown Key West district of Key West, only 1.4 km from USCGC Ingham Maritime Museum, the 1-bedroom Kw49A Papa Villa Key West comes with a swimming pool for guests to unwind. More

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An Ocean Serenity

109 Front Street #211, Key West, United States Show map

Situated just a 9-minute walk from the natural history museum "Florida Keys Eco-Discovery Center", the 2-bedroom An Ocean Serenity Key West villa offers guests to relax by an outdoor swimming pool. More

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Walkable Home W/ Deck, Office & More In Key West

1121 Watson St Unit 1, Key West, United States Show map

Located approximately 25 minutes' walk from Key West First Legal Rum Distillery, the 1-bedroom Walkable Home W/ Deck, Office & More In Key West has an outdoor swimming pool and is ideal for up to 4… More

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Valhalla - Southernmost Oasis

641 United St, Key West, United States Show map

Situated just a 6-minute stroll from Key West Butterfly and Nature Conservatory, the 2-bedroom Valhalla - Southernmost Oasis Key West villa is suitable for 4 guests and provides a swimming pool to… More

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Sago Palm

536 Porter Lane, Key West, United States Show map

Located a mere 10 minutes' walk from the downtown commercial zoned Duval Street, Sago Palm Villa Key West features an outdoor swimming pool and can accommodate up to 4 guests. Located in the vicinity… More

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Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 20

700 Thomas Street, Key West, United States Show map

Located merely 500 metres from the even Southernmost Point, the 8-bedroom Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 20 provides a heated pool, a Jacuzzi for a more relaxing… More

From US$ 4655 Book Now

Conch Get Enough

546 Porter Lane, Key West, United States Show map

Situated only a 9-minute walk from The Ernest Hemingway Home and Museum, the 2-bedroom Conch Get Enough Villa Key West is ideal for up to 4 guests. This holiday home features opportunities for… More

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Brand New Build Larkshine House - Pool

Mangrove Lane 9, Key West, United States Show map

Featuring an outdoor swimming pool, the 8-bedroom Brand New Build Larkshine House - Pool Villa Key West is suitable for up to 18 people and is located about 15 minutes' walk from Key West Tropical… More

From US$ 2514 Book Now

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

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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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

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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

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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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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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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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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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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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