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

Poolside Suite

Olivia Street 517, Key West, United States View map

Featuring a swimming pool, the spacious 1-bedroom Poolside Suite Key West is around 5 minutes' walk from Duval Street. This 60 m^2 apartment with a patio is located a short distance from Saint Paul's… More

From US$ 914 Book Now

Havana Vieja At Azul Mansion Key West

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

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From US$ 522 Book Now

Flor De Cana At Azul Mansion Key West

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

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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

The Truman Room At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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The Cornish Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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Alligator Reef Light Suite

419 Truman Avenue #1 F, Key West, United States View map

The 1-bedroom Alligator Reef Light Suite Key West villa provides easy access to various city attractions, such as the downtown commercial zoned Duval Street, situated nearly 5 minutes' walk away. More

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Aria At Azul Mansion Key West

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

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From US$ 889 Book Now

Sombrero Reef Light Suite

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

The 1-bedroom Sombrero Reef Light Suite Key West villa offers swift access to various city sites, such as Key West Lighthouse and Keeper's Quarters Museum, situated nearly 5 minutes' walk away. More

From US$ 429 Book Now

Flaglers Oasis By Avantstay Private Pool In Key West Month Long Stays Only

2209 Flagler Ave Is #B, Key West, United States View map

The 2-bedroom villa is nearly a 10-minute stroll from Smathers Beach and within walking distance of Peace Covenant Presbyterian Church. Guests, staying at the villa, can use an equipped kitchenette… More

From US$ 181 Book Now

The Mallory Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

Along with proximity to the 19 - acre Key West Cemetery, just a 9-minute walk away, The Mallory Suite At Inn On Fleming Key West! villa offers opportunities for windsurfing, snorkelling, and fishing… More

From US$ 441 Book Now

Sunrise Suites Bonaire Suite #210

Key West, United States View map

Featuring an outdoor swimming pool, the spacious 2-bedroom Sunrise Suites Bonaire Suite #210 Key West is 6 minutes' stroll from Cow Key Channel. Guests can take advantage of a hot tub to enhance… More

From US$ 197 Book Now

Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom

915 Eisenhower Drive, Key West, United States View map

The 2-bedroom Dominica - New Waterfront Condo Pool Dock 2 Bedroom 2 Bathroom Key West villa is located around 5 minutes' walk from Wreckers Sloop Mary and offers guests to relish a patio as well as a… More

From US$ 776 Book Now

St John - Downtown Waterfront Penthouse Pool Parking Dock

915 Eisenhower Drive, Key West, United States View map

The 4-bedroom St John - Downtown Waterfront Penthouse Pool Parking Dock Villa Key West is located only 6 minutes' walk from the C. B. Harvey Rest Beach Park and offers guests to relish a patio as… More

From US$ 1691 Book Now

Duval Street Suite W Kitchen And Shared Heated Pool

824 Duval Street, Key West, United States View map

Located 7 minutes' walk from Duval Street and The Ernest Hemingway Home and Museum, Duval Street Suite W Kitchen And Shared Heated Pool Key West features views of the city. Situated within close… More

From US$ 501 Book Now

Duval Sea Turtle By Avantstay Great Location Close To Shops Shared Pool

1075-29 Duval Square, Key West, United States View map

This 2-bathroom villa is at 300 metres from The Ernest Hemingway Home and Museum and walking distance from the even Southernmost Point. The Key West villa also features a kitchen and amenities such… More

From US$ 551 Book Now

Brisa Del Mar By Avantstay Communal Pool Gated Community Ocean Front

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

The 2-bedroom villa offers accommodation only 1.2 km from Higgs Beach, while Key West Firehouse Museum is a 20-minute walk away. This villa also comes with a fully-fitted kitchen complete with… More

From US$ 615 Book Now

New The Windrose House - Pool & Pets

Shoreline Road 3, Key West, United States View map

The 6-bedroom New Windrose House By Brightwild - Pool & Pets Villa is at a 7 km distance from Key West Firehouse Museum and it takes 10 minutes to drive to Key West International airport. The… More

From US$ 2971 Book Now

New Private Pool & Docking - Floralee House

Mangrove Lane 11, Key West, United States View map

**Discover the Charm of New Private Pool & Docking - Floralee House Villa Key West** Nestled in the enchanting surroundings of Key West, New Private Pool & Docking - Floralee House invites you to… More

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Always Your Paradise By Avantstay Shared Pool Near Zachary Beach Month-Long Stays Only

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

Staying at the 1-bedroom Always Your Paradise By Avantstay Shared Pool Near Zachary Beach Month-Long Stays Only Key West villa, guests can visit the Key West Aquarium, which is just 1 km away. More

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New Rose Petal Petite Suite - Pool & Parking

Rose Lane 526, Key West, United States View map

To enjoy your vacation in Key West, stay at the spacious 74 m^2 New Rose Petal Petite Suite - Pool & Parking Key West, which is within a 5-minute drive of Higgs Beach Dog Park and just 650 metres… More

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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

Sunrise Suites Antigua Suite #312

Key West, United States View map

Located approximately 10 minutes by car from the historic West Martello Tower, the 2-room Sunrise Suites Antigua Suite #312 Key West is within a 15-minute drive of a top family-friendly place like… More

From US$ 166 Book Now

The Elizabeth Suite

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

Situated just a 5-minute stroll from The Unitarian Universalist Fellowship of Key West, the 1-bedroom The Elizabeth Suite Key West villa offers easy access to numerous tourist spots in the area. More

From US$ 383 Book Now

Brand New Catchlight House With Private Pool

Mangrove Lane 7, Key West, United States View map

The 7-bedroom Brand New Catchlight House With Private Pool Villa Key West is located around a 25-minute walk from Key West Tropical Forest and Botanical Garden and provides fishing for active guests. More

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The Fleming Suite

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

Nestled a 20-minute walk from The Ernest Hemingway Home and Museum, The Fleming Suite Key West villa entices guests to explore various tourist destinations nearby. More

From US$ 357 Book Now

Paradise Place By Avantstay Key West Old Town Condo W Shared Pool

905 White St #1, Key West, United States View map

The 1-bedroom Paradise Place By Avantstay Key West Old Town Condo W Shared Pool is located 15 minutes' walk from C. B. Harvey Rest Beach Park and offers quick access to the Minor Saint Mary Star of… More

From US$ 789 Book Now

Sunrise Suites Big Kahuna Suite #202

Key West, United States View map

The spacious 72 m^2 Sunrise Suites Big Kahuna Suite #202 Key West is situated in Key West, around 10 minutes' drive from Higgs Beach, and offers spa amenities such as a hot tub. Cow Key Channel is a… More

From US$ 339 Book Now

Tranquility By Avantstay Close To Duval St W Bbq Shared Pool

714-5 Olivia St, Key West, United States View map

Located in the Downtown Key West district with The Ernest Hemingway Home and Museum nearby, the 1-bedroom Tranquility By Avantstay Close To Duval St W Bbq Shared Pool lies a mere 1.2 km from Higgs… More

From US$ 400 Book Now

Julie At Scarlet Mango Inn Key West

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

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Bayview North One

801 Eisenhower Dr. #4, 4, Key West, United States View map

Set in the vibrant heart of Key West, Bayview North One Villa offers an idyllic retreat for travelers seeking comfort and convenience. Just 2 kilometers from the picturesque shores of South Beach and… More

From US$ 1220 Book Now

Golf Course Oasis With Private Yard, 5 Mi To Duval!

28 Merganser Ln, Key West, United States View map

Situated approximately 5 minutes' walk from the Key Haven, the 2-bedroom Golf Course Oasis With Private Yard, 5 Mi To Duval! Villa Key West offers easy access to numerous tourist spots in the area. More

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Honey At Scarlet Mango Inn Key West

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

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Sundown Refuge By Avantstay Top Location W Patio Outdoor Dining Shared Pool Month Long Stays

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

The 2-room Sundown Refuge By Avantstay Top Location W Patio Outdoor Dining Shared Pool Month Long Stays Key West apartment lies in the Downtown Key West district of Key West and offers swift access… More

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Bahamian Reed By Avantstay Walk To Everything W Community Pool Month Long Stays Only

510 Porter Lane, Key West, United States View map

The welcoming Bahamian Reed By Avantstay Walk To Everything W Community Pool Month Long Stays Only Key West villa offers proximity to such city sites as Fort Zachary Taylor State Park, located… More

From US$ 434 Book Now

Contra House -Luxury Home With Pool

Simonton Street 720, Key West, United States View map

Situated in Key West, at 750 metres of Key West Firehouse Museum, the 4-bedroom New Listing Palm Escape- Luxury Home W Pool provides accommodation with complimentary parking and a swimming pool. This… More

From US$ 1909 Book Now

Island Oasis

101 Front Street, #25, Key West, United States View map

Situated merely 7 minutes' stroll from the Key West Aquarium, Island Oasis Villa Key West offers quick access to numerous city landmarks nearby. More

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Carpe Dium

1800 Atlantic Blvd Unit C119, Key West, United States View map

Front Street is set within 10 minutes' drive of the 2-bedroom Carpe Dium Villa. The accommodation also has a full kitchen with a microwave oven, coffee/tea making equipment and fridges. More

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The Ebberly House - Amazing Pool In Gated Community

Shoreline Road 1, Key West, United States View map

The 7-bedroom and 7-bathroom villa is situated nearly a 25-minute walk from Key West Tropical Forest and Botanical Garden and at a 4 km distance from Fort East Martello Museum. This accommodation has… More

From US$ 4783 Book Now

Suncoast House -Pool & Boat Dock

Shoreline Road 12, Key West, United States View map

Nautical Splendor Villa is at a 7 km distance from the 19-acre Key West Cemetery and approximately 10 minutes' drive from from Fort East Martello Museum. There is a kitchen with a microwave, a… More

From US$ 1786 Book Now

Ashe Street Serenade

613 Ashe Street, Key West, United States View map

**Ashe Street Serenade: A Tropical Retreat in Key West** Nestled just 5 km from the sparkling shores of Key West International, Ashe Street Serenade offers a charming escape infused with vibrant… More

From US$ 390 Book Now

Fuente At Azul Mansion Key West

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

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From US$ 463 Book Now

The Hemingway Suite At Inn On Fleming Key West!

1016 Fleming St., Key West, United States View map

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Upper Bayview North

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

Situated a 5-minute walk from the Wreckers Sloop Mary, Upper Bayview North Villa Key West entices guests with views of the sea. More

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Prime Old Town Location W Pool Walk To Duval Steet Blue Heron By Avantstay

906-2 Truman Avenue, Key West, United States View map

The 2-bedroom Prime Old Town Location W Pool Walk To Duval Steet Blue Heron By Avantstay Key West villa offers quick access to such city attractions as the Key West Firehouse Museum, located about a… More

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3 Bedroom 2Ba Private Pool Waterfront

West Cypress Terrace 11, Key West, United States View map

Located 7 km from the Key West Historic Seaport, 3 Bedroom 2Ba Private Pool Waterfront Stock Island villa gives access to various tourist sites in the vicinity. More

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A Sunset Peace

109 Front Street #210, Key West, United States View map

A Sunset Peace Villa Key West offers quick access to such city attractions as the Curry Mansion, located just a 6-minute walk away. More

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Southern Palms

Whitehead Street 729, Key West, United States View map

The 5-bedroom Southern Palms Villa is located in the Duval district a few metres from the 19-acre Key West Cemetery and offers complimentary parking and an outdoor swimming pool. The Key West villa… More

From US$ 2203 Book Now

Gulf Getaway

Porter Lane 524, Key West, United States View map

Perfectly positioned just a short drive from the heart of Key West, the Gulf Getaway provides easy access to historic sites, vibrant nightlife, and pristine beaches. More

From US$ 342 Book Now

Sugar Palm Suite At Travelers Palm Inn Key West

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

Situated in the Downtown Key West district of Key West, a mere 1.6 km from the historic fort "West Martello Tower", Sugar Palm Suite At Travelers Palm Inn Key West villa comes with a swimming pool… More

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