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2026-04-18
2026-04-19
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Hotels with indoor pool in Key West

Happy Hour Haven

620 Thomas St #285, Key West, United States View map

Located a 6-minute walk from the downtown commercial zoned Duval Street and San Carlos Institute, the spacious Happy Hour Haven Apartment Key West features views of the pool. Also, there is an… More

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Dock And Balcony Serene Big Coppitt Key Escape

3 Palmetto Dr, Key West, United States View map

Located a few steps from East Rockland Key Island, the 2-bedroom Dock And Balcony Serene Big Coppitt Key Escape Key West villa includes a patio with views of the garden. Offering a private swimming… More

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A Conch Escape

620 Thomas Street #274, Key West, United States View map

Located a 17-minute walk from the waterfront Mallory Square, A Conch Escape Villa Key West gives access to various tourist sites in the vicinity. More

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Upper Sunset South

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

**Welcome to Upper Sunset South** Nestled in the heart of Key West, Upper Sunset South offers a serene coastal retreat designed with relaxation in mind. More

From US$ 951 Book Now

Breezy Bungalow By Avantstay Close 2 Zachary Taylor State Park W Shared Pool Month-Long Stays

550 Porter Lane, Key West, United States View map

Situated merely 1.9 km from the US 1 Mile Marker 0, the 0-bedroom Breezy Bungalow By Avantstay Close 2 Zachary Taylor State Park W Shared Pool Month-Long Stays Key West invites guests to relax at a… More

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Foster'S Folly

Snapper Lane, Key West, United States View map

The 2-bedroom Foster'S Folly Villa Key West is located 2.6 km from Blue Hole Lake, giving access to various tourist spots nearby. More

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A Latitude Adjustment

101 Front Street, #17, Key West, United States View map

A Latitude Adjustment Villa Key West offers proximity to such city sites as the US 1 Mile Marker 0, located nearly a 5-minute walk away. More

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Doc'S Paradise

61 Spoonbill Way, Key West, United States View map

The 3-bedroom Doc'S Paradise Key West villa offers quick access to such tourist spots as FYT Fitness Center, situated only a 6-minute walk away. Offering a Jacuzzi, this Key West holiday home is 3.9… More

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Boat House By Avantstay Character Cottage Central Location W Shared Pool Month Long Stays

711 Bakers Lane, Key West, United States View map

Simonton Beach is situated less than 10 minutes on foot from this property. The Key West villa is also fitted with 1 bedroom and includes an equipped kitchenette area with coffee/tea makers, a… 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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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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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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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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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

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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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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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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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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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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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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Ecco Domani By Avantstay Gorgeous Home W Pool Balcony In Great Location Month Long Stays Only

1011-2 Simonton St, Key West, United States View map

The villa is set in Key West, 15 minutes' walk from the shopping mall "Clinton Square Market" and about 10 minutes' drive from Key West Garden Club. The Key West villa features 2 bathrooms and boasts… More

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Scarlet At Scarlet Mango Inn Key West

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

Situated 5 minutes' walk from the Key West Express, Scarlet At Scarlet Mango Inn Key West offers a heated pool. More

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Bayview Middle

801 Eisenhower Dr. #5, 5, Key West, United States View map

Set in the enchanting landscapes of Key West, the Bayview Middle Villa seamlessly blends luxurious comfort with the captivating charm of the island. Just 10 km from Key West International Airport… More

From US$ 1078 Book Now

Dune Wind South By Avantstay Communal Pool Hot Tub Gated Community Close To Smathers Beach Month Long Stays Only

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

**Welcome to Dune Wind South, your tranquil haven nestled in a gated community near the pristine shores of Smathers Beach. This inviting beachside extended stay offers unparalleled amenities… More

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Tortugas Harbor Light Suite

419 Truman Avenue #2R, Key West, United States View map

**Welcome to Tortugas Harbor Light Suite, a charming retreat situated in the vibrant heart of Duval.** With its prime location, this splendid accommodation captures the essence of Key West's unique… More

From US$ 805 Book Now

Casita Casa Marina

908 Flagler Avenue, Key West, United States View map

Offering a free private car park in the Downtown Key West district of Key West, the 3-bedroom Casita Casa Marina Villa Key West is also 950 m from significant religious sites like the Minor Saint… 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 4-bedroom Bachelorparty Hq For 16-Feet To Duval-Pool-Hot Tub Villa is situated in Key West, a 10-minute drive from Key West Garden Club and nearly a 9-minute walk from Mile Marker 0 Store. The… More

From US$ 1984 Book Now

An Island Retreat

403B Emma Street, Key West, United States View map

An Island Retreat Villa Key West offers proximity to nearby tourist spots, such as the Mallory Square, situated about 15 minutes' walk away. More

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Corona At Azul Mansion Key West

907 Truman Ave., Key West, United States View map

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From US$ 523 Book Now

Island Paradise

413 Virginia St, Key West, United States View map

Featuring a year-round outdoor swimming pool for guests' enjoyment, Island Paradise Key West villa is nestled right in the centre of Key West, within a 300-metre distance of the Ernest Hemingway Home… More

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The Curry House - Entire Complex

Fleming Street 806, Key West, United States View map

Offering a swimming pool, The Curry House - Entire Complex is set in the Downtown Key West district of Key West only 1.3 km from Mallory Square. More

From US$ 1415 Book Now

A Gulfstream Drift

105 Front Street #319, Key West, United States View map

Situated 6 minutes' walk from the Key West Shipwreck Treasure Museum, A Gulfstream Drift Villa Key West entices guests to explore various tourist attractions in the area. More

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Sago Palm

536 Porter Lane, Key West, United States View map

Sago Palm Villa Key West offers swift access to various city sites, such as Jackson Square, situated just 6 minutes' walk away. More

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Monkey House By Avantstay Pool By Duval Street

709 Bakers Lane, Key West, United States View map

Staying at Monkey House By Avantstay Pool By Duval Street Key West villa, guests can visit the downtown commercial zoned Duval Street, which is only 1 km away. Offering pool views as well as a… More

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Tennessee Williams By Avantstay Funky Design Pool

709 Bakers Lane, Key West, United States View map

Offering pool views, the 0-bedroom Tennessee Williams By Avantstay Funky Design Pool Key West villa is situated a mere 5 minutes' walk from the Duval Street. More

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Serenity By Avantstay Guest House In Old Town W Shared Pool Month Long Stays Only

907 Emma St, Key West, United States View map

This villa is set in Key West, 0.7 km from the even Southernmost Point and within 5 minutes' stroll of The Ernest Hemingway Home and Museum. The Key West villa is composed of 1 bedroom, an equipped… More

From US$ 204 Book Now

Linger Longer By Avantstay Key West Walkable Gated Community Shared Pool Month Long Stays Only

277 Southard Street, Key West, United States View map

Staying at the 1-bedroom Linger Longer By Avantstay Key West Walkable Gated Community Shared Pool Month Long Stays Only villa, guests can visit Southernmost Point of the Continental US Monument… More

From US$ 400 Book Now

Captiva At Azul Mansion Key West

907 Truman Ave., Key West, United States View map

Captiva At Azul Mansion Key West hotel, located only 650 metres from the Higgs Beach and approximately a 15-minute walk from the South Beach, features a heated swimming pool for guests to take a dip… More

From US$ 445 Book Now

Bahama Gardens - 4 Key West Old Town Vacation Rental Homes - Sleeps 23

700 Thomas Street, Key West, United States View map

**Bahama Gardens - A Tropical Retreat in Key West** Situated a mere 10 km from Key West International Airport, Bahama Gardens strikes the perfect balance between accessibility and seclusion, offering… More

From US$ 4655 Book Now

Carysfort Reef Light Suite

217 Eanes Ln, Key West, United States View map

Situated only a 5-minute walk from the Ernest Hemingway Home and Museum, Carysfort Reef Light Suite Key West villa entices guests with views of the sea. More

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Catch Of The Day

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

Catch Of The Day Villa Key West is located merely a 14-minute walk from the Ernest Hemingway Home and Museum, giving access to various tourist spots nearby. More

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A Bella Capri

1423 Patricia Street, Key West, United States View map

A Bella Capri Villa Key West is located nearly a 25-minute walk from the downtown commercial zoned Duval Street, giving access to various tourist spots nearby. More

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Road'S End

Center Street 921, Key West, United States View map

Welcome to the enchanting **Road's End Apartment Key West**, where vibrant island life meets modern comfort. Nestled in the heart of Key West, this exceptional abode places you just 700 metres from… More

From US$ 488 Book Now

Key Lime Pie By Avantstay Ideal Location W Splash Pool Out Door Dining Month Long Stays Only

1018 Thompson Lane, Key West, United States View map

Set at 600 metres of Nancy Forrester's Secret Garden and 0.8 km from Simonton Street, the villa is located in Key West. A kitchen with a refrigerator, an oven and kitchenware is included at this Key… More

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Royal Palm Studio At Travelers Palm Inn Key West

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

Along with proximity to the Minor Saint Mary Star of the Sea Basilica, only 5 minutes' walk away, Royal Palm Studio At Travelers Palm Inn Key West villa offers opportunities for windsurfing… More

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