Special offers and Exclusive deals

Search Hotels

2026-11-14
2026-11-15
Guests

Filter Results

Hotels by class

Hotel name

Price per night

Accommodation type

Districts

Attractions

Thematic hotels

Review rating

Hotel facilities

Room facilities

Apply Filters
Clear Filters

Hotels with indoor pool in Key West

Blue Haven Unit B416

1800 Atlantic Blvd, Unit B416, Key West, United States View map

Located just 600 metres from the Higgs Beach Dog Park, the 2-bedroom Blue Haven Unit B416 Villa Key West provides an outdoor swimming pool as well as windsurfing, snorkelling, and canoeing to… More

From US$ 1571 Book Now

Banana Split

Caroline Street 537, Key West, United States View map

For those traveling to the area, the nearest airport is conveniently located just 4 km away, ensuring an easy arrival and departure. More

From US$ 383 Book Now

Atlantic Paradise Found

1800 Atlantic Blvd C232, Key West, United States View map

Welcome to Atlantic Paradise, a luxurious enclave nestled in the heart of Key West, where comfort meets coastal charm. Just a short 5 km from Key West International Airport, this exquisite retreat… More

From US$ 674 Book Now

Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock

915 Eisenhower Drive, Key West, United States View map

The 2-bedroom Florida - Spacious Updated Waterfront Condo 2X2 Pool Dock Key West villa, located approximately 5 minutes' walk from the Wreckers Sloop Mary, can host up to 8 guests. This accommodation… More

Book Now

The Crestwood House - Private Heated Pool & Parking

Shoreline Road 17, Key West, United States View map

The 6-bedroom The Crestwood House - Private Heated Pool & Parking Villa Key West entices active guests with access to a fitness room and is located just 11 minutes' walk from FYT Fitness Center. More

From US$ 2726 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

Book Now

New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool

Duval Street 1075, Key West, United States View map

Up to 6 guests can stay at the 2-bedroom New Casa Caribe By Brightwild- Two-Story Condo Rooftop Pool Key West and enjoy the Key West Lighthouse and Keeper's Quarters Museum, located approximately a 5… More

From US$ 343 Book Now

Evershore House -Pool, Parking, Dock!

Key Haven Terrace 2, Key West, United States View map

Situated merely 1.6 km from Sheriff s Animal Farm, the 4-bedroom Evershore House -Pool, Parking, Dock! Key West villa features a patio with views of the sea. Offering a private swimming pool, the… More

From US$ 3115 Book Now

Contra House -Luxury Home With Pool

Simonton Street 720, Key West, United States View map

Situated within 5 minutes' walk of the downtown commercial zoned Duval Street, the 4-bedroom Contra House -Luxury Home With Pool Key West offers opportunities for cycling and fishing in the area. More

From US$ 1909 Book Now

Tranquility By Avantstay

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

Located in the Downtown Key West district of Key West, a mere 6 minutes' walk from the Minor Saint Mary Star of the Sea Basilica, the 0-bedroom Tranquility By Avantstay Key West villa offers patio… More

From US$ 448 Book Now

The Breeze

1901 South Roosevelt Blvd, Unit 301 East, Key West, United States View map

During the stay at The Breeze Villa Key West, guests can indulge in windsurfing, snorkelling, and fishing or visit Southernmost Point of the Continental US Monument, located 25 minutes' stroll away. More

Book Now

Key West On My Mind

1800 Atlantic Blvd Unit A305, Key West, United States View map

Located only a 9-minute walk from the Higgs Beach Dog Park, the 2-bedroom Key West On My Mind Villa features an outdoor swimming pool and can accommodate up to 6 guests. Offering a Jacuzzi and a… More

From US$ 583 Book Now

Coconut Palm

Whitehead Street 729, Key West, United States View map

**Coconut Palm Villa Key West** invites guests to experience the vibrant ambiance of Duval Street, where island-inspired charm meets contemporary luxury. Nestled amid a lively backdrop, this oasis… More

From US$ 1683 Book Now

Aria At Azul Mansion Key West

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

Located nearly 5 minutes' walk from the Key West Firehouse Museum, the comfortable Aria At Azul Mansion Key West Hotel gives easy access to various tourist attractions. Offering a heated swimming… More

From US$ 351 Book Now

The Independent Inn (Adults Only)

412 Frances Street, Key West, United States View map

Located 2.2 km from Southernmost Point of the Continental US Monument, the comfortable The Independent Inn Key West offers air-conditioned rooms approximately a 20-minute walk from the historical Key… More

From US$ 322 Book Now

Curry House - Room 5

Fleming Street 806, Key West, United States View map

Nestled in the Downtown Key West district of Key West, just 1.3 km from the downtown commercial zoned Duval Street, the comfortable Curry House - Room 5 Key West hotel offers a patio. Providing… More

From US$ 346 Book Now

Flor De Cana At Azul Mansion Key West

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

Featuring an outdoor swimming pool, the comfortable Flor De Cana At Azul Mansion Key West hotel is located in the Downtown Key West district, approximately 25 minutes' walk from the Smathers Beach. More

From US$ 346 Book Now

The Simonton Room At Inn On Fleming Key West

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

The comfortable 3-star The Simonton Room At Inn On Fleming Key West, located only 1.4 km from the Ripley's Believe It or Not, offers an outdoor swimming pool and Wi-Fi in the rooms. This Key West… More

From US$ 500 Book Now

Havana Vieja At Azul Mansion Key West

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

The comfortable Havana Vieja At Azul Mansion Key West hotel offers easy access to the historic Saint Mary Star of the Sea Church, which is situated approximately a 5-minute walk away. Offering a… More

From US$ 328 Book Now

Bunk Room At The Grand Maloney

Caroline Street 529, Key West, United States View map

Offering an outdoor swimming pool, the comfortable Bunk Room At The Grand Maloney Key West hotel is nestled in Duval with leather arm chairs and couches all surrounded by glimmering candles and chic… More

From US$ 370 Book Now

The Truman Room At Inn On Fleming Key West!

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

Located merely 1.1 km from the downtown commercial zoned Duval Street, the comfortable The Truman Room At Inn On Fleming Key West! is approximately 5 minutes' walk from Turtle Cannery Maritime Museum… More

From US$ 340 Book Now

The Whitehead Room At Inn On Fleming Key West!

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

The Whitehead Room At Inn On Fleming Key West! is a great place to stay in the Downtown Key West district, a 25-minute walk from Southernmost Point of the Continental US Monument. At this guest house… More

From US$ 314 Book Now

Number Eleven At Scarlet Mango Inn Key West

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

The comfortable Number Eleven At Scarlet Mango Inn Key West, located 0.7 km from the Ernest Hemingway Home and Museum and 17 minutes' walk from Southernmost Point of the Continental US Monument… More

From US$ 419 Book Now

The Cornish Suite At Inn On Fleming Key West!

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

Located only 5 minutes on foot from the Key West Historic Seaport, the comfortable 3-star The Cornish Suite At Inn On Fleming Key West! offers guided tour service to ensure you have an unforgettable… More

From US$ 437 Book Now

Ambrosia At Azul Mansion Key West

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

Located merely 0.6 km from the Higgs Beach, the comfortable Ambrosia At Azul Mansion Key West Hotel is nearly a 5-minute walk from the Key West Firehouse Museum. Offering an outdoor swimming pool… More

From US$ 332 Book Now

The Gato Room At Inn On Fleming Key West!

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

The comfortable 3-star The Gato Room At Inn On Fleming Key West! provides guided tour service, and a prime location, just 1.3 km from the Audubon House and Tropical Gardens. Situated in the vicinity… More

From US$ 534 Book Now

Deluxe Queen At The Curry Mansion - Parking & Heated Pool!

Caroline Street 511, Key West, United States View map

Situated just a 7-minute stroll from the Harry S. Truman Little White House, the comfortable Deluxe Queen At The Curry Mansion - Parking & Heated Pool! Key West hotel offers air-conditioned rooms, Wi… More

From US$ 533 Book Now

Honey At Scarlet Mango Inn Key West

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

Offering an outdoor swimming pool, the comfortable Honey At Scarlet Mango Inn Key West is nestled in the Downtown Key West district of Key West, just 13 minutes' walk from the bustling plaza "Mallory… More

From US$ 466 Book Now

Blue Room At The Grand Maloney

Caroline Street 529, Key West, United States View map

Located merely 1.3 km from the natural history museum "Florida Keys Eco-Discovery Center", the comfortable Blue Room At The Grand Maloney Key West hotel offers air-conditioned rooms merely 6 minutes'… More

From US$ 378 Book Now

Cohiba At Azul Mansion Key West

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

The comfortable Cohiba At Azul Mansion Key West Hotel, located nearly 25 minutes' walk from the Smathers Beach, offers an outdoor swimming pool, Wi-Fi in the rooms. This Key West guest house lies in… More

From US$ 262 Book Now

Classic King With Balcony At Curry Mansion

Caroline Street 511, Key West, United States View map

**Welcome to the Classic King With Balcony at Curry Mansion, your serene haven in the heart of Key West.** This enchanting retreat merges contemporary comforts with historic charm, situated perfectly… More

From US$ 372 Book Now

Curry House- 3Rd Floor, King Bed, & Balcony Room 8

Fleming Street 806, Key West, United States View map

The 3-star Curry House- 3Rd Floor, King Bed, & Balcony Room 8 Key West hotel, located only 350 m from The Oldest House Historical Place Museum and 16 minutes' walk from the fully accredited Mel… More

From US$ 205 Book Now

Key Lime Cottage

Caroline Street 537, Key West, United States View map

Offering an outdoor swimming pool, the comfortable Key Lime Cottage Key West hotel is situated in Duval with unique, island inspired Small Plates with bold Caribbean spices and fresh local seafood… More

From US$ 363 Book Now

Cortez At Azul Mansion Key West

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

Offering air-conditioned rooms and Wi-Fi in the rooms, the comfortable Cortez At Azul Mansion Key West hotel is about 2 km from Mile Marker 0 Store and approximately a 20-minute walk from the natural… More

From US$ 304 Book Now

Curry House - Room 1

Fleming Street 806, Key West, United States View map

The comfortable Curry House - Room 1 Key West hotel is nestled nearly 5 minutes' walk from the vintage parish "Saint Paul's Episcopal Church of Key West" and features a heated pool. While staying at… More

From US$ 234 Book Now

Honey Bun Hideaway

Caroline Street 537, Key West, United States View map

Honey Bun Hideaway Hotel - A Tropical Escape in Key West Culinary enthusiasts will rejoice in the hotel's location, where guests can savor one of Key West's premier dining experiences just moments… More

From US$ 237 Book Now

Curry House - Pool, King Bed & Balcony! Room 7

Fleming Street 806, Key West, United States View map

Offering air-conditioned rooms, the 3-star Curry House - Pool, King Bed & Balcony! Room 7 Key West hotel is just a 5-minute walk from the Vandenberg Wreck. At the aparthotel, located only steps away… More

From US$ 301 Book Now

Yellow Room At Grand Maloney

Caroline Street 529, Key West, United States View map

**Discover an Oasis in the Heart of Key West** Nestled amidst the vibrant energy of downtown Key West, the Grand Maloney offers a contemporary retreat in a historically restored two-story brick home. More

From US$ 353 Book Now

Deluxe King - Curry Mansion With Pool!

Caroline Street 511, Key West, United States View map

Located merely 1.7 km from the South Beach, the comfortable Deluxe King - Curry Mansion With Pool! Hotel Key West is merely 6 minutes' walk from the bustling plaza "Mallory Square". Offering views of… More

From US$ 396 Book Now

Fontana At Azul Mansion Key West

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

Located merely 1.7 km from the fully accredited Mel Fisher Maritime Heritage Museum, the comfortable Fontana At Azul Mansion Key West Hotel is about 5 minutes' walk from Saint Mary Star of the Sea… More

From US$ 205 Book Now

Scarlet At Scarlet Mango Inn Key West

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

Featuring Wi-Fi in the rooms, Scarlet At Scarlet Mango Inn Key West sits 12 minutes' walk from the Key West Aquarium. At this guest house, located within reach of the Ernest Hemingway Home and Museum… More

From US$ 506 Book Now

Claro At Azul Mansion Key West

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

The comfortable Claro At Azul Mansion Key West Hotel, located only 0.6 km from the very unusual Key West Cemetery and around a 25-minute walk from the Key West Aquarium, features a heated swimming… More

From US$ 320 Book Now

Golden Nugget At Scarlet Mango Inn Key West

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

The comfortable Golden Nugget At Scarlet Mango Inn Key West offers easy access to the San Carlos Institute, which is situated approximately a 5-minute walk away. Offering a heated swimming pool along… More

From US$ 388 Book Now

The Flagler Room At Inn On Fleming Key West!

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

Featuring Wi-Fi in the rooms, the 3-star The Flagler Room At Inn On Fleming Key West! is just 1.9 km from the secluded pocket Dog Beach. At the guest house, located a short way from the Key West… More

From US$ 418 Book Now

Carriage House At Grand Maloney

Caroline Street 529, Key West, United States View map

Standing just a 6-minute walk from the Key West Aquarium, the comfortable Carriage House At Grand Maloney Hotel Key West offers an outdoor swimming pool. The hotel also includes a car park. More

From US$ 350 Book Now

Your Key West Fantasy Fest Week Escape Awaits Oct 17-24, 2026

3675 South Roosevelt Boulevard 5-231, Key West, United States View map

More

Book Now

Julie At Scarlet Mango Inn Key West

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

The comfortable Julie At Scarlet Mango Inn Key West is nestled just 650 metres from the 19-acre Key West Cemetery and features an outdoor swimming pool. There is Wi-Fi, provided in the rooms. More

From US$ 410 Book Now

The Hemingway Suite At Inn On Fleming Key West!

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

The comfortable 3-star The Hemingway Suite At Inn On Fleming Key West! provides guided tour service, and a convenient location, just 1.2 km from The Oldest House Historical Place Museum. Situated in… More

From US$ 556 Book Now

Fuente At Azul Mansion Key West

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

The comfortable Fuente At Azul Mansion Key West Hotel, located only 1.3 km from the even Southernmost Point, offers an outdoor swimming pool and Wi-Fi in the rooms. Thanks to its prime location, this… More

From US$ 325 Book Now

Keitt At Scarlet Mango Inn Key West

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

Located just 1.9 km from the Bayview Park, the comfortable Keitt At Scarlet Mango Inn Key West is nearly 5 minutes' walk from the downtown commercial zoned Duval Street. Offering an outdoor swimming… More

From US$ 399 Book Now