Hotels with Pools in Key West
Find the hotels with pools that appeal to you the most
The best hotels with pools in Key West
Check out our selection of great hotels with pools in Key West
Filter by:
The Capitana Key West
Located in Key West, 1.3 miles from Smathers Beach, The Capitana Key West has accommodations with an outdoor swimming pool, free private parking, a fitness center and a private beach area.
Southernmost Point Guest House & Garden Bar
This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 361 feet from the Southernmost Point and 240 feet from the beach.
Douglas House
Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available.
Simonton Court Historic Inn & Cottages
Located in Key West, this Florida adult-only inn offers complimentary, light continental breakfast and free Wi-Fi access.
Weatherstation Inn Circa 1911
Set within 1640 feet of Key West Aquarium, Weatherstation Inn Circa 1911 is an adult-only bed and breakfast in Key West and features a number of amenities including an outdoor swimming pool and a...
H2O Suites- Adults Only
This adult-only Key West H2O Suites is 656 feet from Duval Street and features a year-round outdoor rooftop pool with a sun terrace. Guests can enjoy the on-site bar.
Island City House
Offering an outdoor pool, this historic Key West Island City House hotel is 2 minutes’ walk from the Key West sea port. Features include free WiFi, garden, and rooms with a kitchen.
The Mermaid & The Alligator
Featuring an outdoor swimming pool, a garden as well as a shared lounge, The Mermaid & The Alligator is located in the center of Key West, a 11-minute walk from South Beach.
Hyatt Vacation Club at Windward Pointe
This Hyatt Windward Pointe is located in Key West, 3.5 mi from the Southernmost Point, and features a year-round outdoor pool and hot tub. A fully equipped kitchen is provided in every apartment.
Hyatt Vacation Club at Beach House
Hyatt Beach House Resort is located in Key West 4 mi from Duval Street. An outdoor pool and hot tub are featured.
Top picks for Key West hotels
Explore our most popular hotels in Key West
- Scored out of 10, guest rating 8.2Very Good - What previous guests thought, 1,195 reviewsFrom$1291 night, 2 adults
- Scored out of 10, guest rating 8.6Excellent - What previous guests thought, 1,248 reviewsFrom$2391 night, 2 adults
- Scored out of 10, guest rating 9.0Wonderful - What previous guests thought, 444 reviewsFrom$2341 night, 2 adults
- Scored out of 10, guest rating 9.1Wonderful - What previous guests thought, 905 reviewsFrom$2571 night, 2 adults
- Scored out of 10, guest rating 8.3Very Good - What previous guests thought, 1,883 reviewsFrom$1251 night, 2 adults
- Scored out of 10, guest rating 7.9Good - What previous guests thought, 1,897 reviewsFrom$1251 night, 2 adults
- Scored out of 10, guest rating 9.1Wonderful - What previous guests thought, 2,557 reviewsFrom$2061 night, 2 adults
- Scored out of 10, guest rating 8.4Very Good - What previous guests thought, 2,346 reviewsFrom$1591 night, 2 adults
- Scored out of 10, guest rating 9.4Wonderful - What previous guests thought, 300 reviewsFrom$2581 night, 2 adults
- Scored out of 10, guest rating 7.4Good - What previous guests thought, 974 reviewsFrom$1461 night, 2 adults
- Scored out of 10, guest rating 8.3Very Good - What previous guests thought, 525 reviewsFrom$2471 night, 2 adults
- Scored out of 10, guest rating 8.1Very Good - What previous guests thought, 1,006 reviewsFrom$1071 night, 2 adults
- Scored out of 10, guest rating 8.5Very Good - What previous guests thought, 1,192 reviewsFrom$1491 night, 2 adults
- Scored out of 10, guest rating 8.9Excellent - What previous guests thought, 449 reviewsFrom$1591 night, 2 adults
- Scored out of 10, guest rating 7.9Good - What previous guests thought, 1,360 reviewsFrom$1791 night, 2 adults
- Scored out of 10, guest rating 8.5Very Good - What previous guests thought, 634 reviewsFrom$2271 night, 2 adults
- Scored out of 10, guest rating 9.4Wonderful - What previous guests thought, 302 reviewsFrom$2411 night, 2 adults
- Scored out of 10, guest rating 8.0Very Good - What previous guests thought, 306 reviewsFrom$1881 night, 2 adults
- Scored out of 10, guest rating 7.9Good - What previous guests thought, 626 reviewsFrom$1681 night, 2 adults
- Scored out of 10, guest rating 8.5Very Good - What previous guests thought, 1,411 reviewsFrom$2101 night, 2 adults
Filter by:
The Capitana Key West
Located in Key West, 1.3 miles from Smathers Beach, The Capitana Key West has accommodations with an outdoor swimming pool, free private parking, a fitness center and a private beach area.
Southernmost Point Guest House & Garden Bar
This Key West, Florida Southernmost Point Guest House & Garden Bar is located on Duval Street 361 feet from the Southernmost Point and 240 feet from the beach.
Douglas House
Located just 2 minutes’ walk from the Ernest Hemingway Home and Museum, this adult-only inn features free parking and a shared outdoor swimming pool. Free Wi-Fi is also available.
Simonton Court Historic Inn & Cottages
Located in Key West, this Florida adult-only inn offers complimentary, light continental breakfast and free Wi-Fi access.
Weatherstation Inn Circa 1911
Set within 1640 feet of Key West Aquarium, Weatherstation Inn Circa 1911 is an adult-only bed and breakfast in Key West and features a number of amenities including an outdoor swimming pool and a...
H2O Suites- Adults Only
This adult-only Key West H2O Suites is 656 feet from Duval Street and features a year-round outdoor rooftop pool with a sun terrace. Guests can enjoy the on-site bar.
Island City House
Offering an outdoor pool, this historic Key West Island City House hotel is 2 minutes’ walk from the Key West sea port. Features include free WiFi, garden, and rooms with a kitchen.
The Mermaid & The Alligator
Featuring an outdoor swimming pool, a garden as well as a shared lounge, The Mermaid & The Alligator is located in the center of Key West, a 11-minute walk from South Beach.
Hyatt Vacation Club at Windward Pointe
This Hyatt Windward Pointe is located in Key West, 3.5 mi from the Southernmost Point, and features a year-round outdoor pool and hot tub. A fully equipped kitchen is provided in every apartment.
Hyatt Vacation Club at Beach House
Hyatt Beach House Resort is located in Key West 4 mi from Duval Street. An outdoor pool and hot tub are featured.
Looking for a hotel with pools?
Most booked hotels with pools in Key West and surrounding area in the past month
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Popular with guests booking hotels with pools in Key West
Enjoy breakfast in Key West and nearby
Wicker Guesthouse
Located one block from the Ernest Hemingway House and Museum in Key West, Florida, this guesthouse has a large tropical garden and an outdoor pool. Rooms feature free Wi-Fi.
Lighthouse Hotel - Key West Historic Inns
Lighthouse Hotel is located in the heart of iconic Key West, opposite the Ernest Hemingway Home and Museum and the Keeper's Quarters Museum.
Duval House
Located centrally on lively Duval Street, Duval House offers a continental breakfast that includes Belgian waffles. The 7 Caribbean-style buildings offer free WiFi.
Truman Hotel
This trendy Key West boutique hotel features an outdoor pool and modern rooms equipped with iPod docking stations and flat-screen TVs. South Beach - Key West is 0.5 miles away from the property.
Paradise Inn - Adult Exclusive
Paradise Inn - Adult Exclusive is located in Key West and features landscaped grounds with brick paths and a lotus pond with koi and tropical turtles.
Located above a nightclub on historic Duval Street in Key West, Florida, this gay male guest house features an outdoor swimming pool, a clothing-optional sundeck, and an on-site restaurant.
Ella's Cottages - Key West Historic Inns
Offering a heated outdoor pool, this boutique Ella's Cottages is located in Old Town Key West 2 minutes' walk from Duval Street. Free WiFi and a poolside continental breakfast are provided.
Duval Inn - Key West
Offering an outdoor pool, Duval Inn is located in Key West. Free WiFi access is available. This Key West bed and breakfast includes both an indoor and outdoor seating area as well as a refrigerator.
Save money on pools in Key West and nearby – budget options available
Lighthouse Suites Collection
Lighthouse Suites Collection is located in Key West, just a 15-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. Featuring sea views, this vacation home also features free Wifi.
Key West Light Suite
Key West Light Suite is located in Key West, just a 15-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. Featuring sea views, this vacation home also comes with free Wifi.
BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub
BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub is located in Key West, just a 15-minute walk from Key West Aquarium and 0.8 miles from Mallory Dock.
Old Town Garden Villas - Andros Suite
Old Town Garden Villas - Andros Suite offers accommodations in Key West, a 16-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. The apartment has access to a restaurant.
Andrews Inn & Garden Cottages
Located right off Duval Street, the Andrews Inn and Garden Cottages are less than 5 minutes’ walk from various dining and entertainment options. Guests can enjoy free WiFi and an outdoor pool.
Old Town Garden Villas - Abaco Suite
Old Town Garden Villas - Abaco Suite is located in Key West, just a 17-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. The apartment has access to a restaurant.
Casa Havana @ Duval Square R22
Casa Havana @ Duval Square R22 is located in Key West, just a 17-minute walk from Key West Aquarium and 0.9 miles from Mallory Dock. Guests can benefit from a terrace and an outdoor pool.
Casa Key West-Pool & Free Parking
Casa Key West-Pool & Free Parking offers accommodations in Key West, a 19-minute walk from Key West Aquarium and one mile from Mallory Dock.
Great access to the city center. Check these hotels with pools in Key West and nearby
The Casablanca Hotel
Less than 2 minutes’ walk from the Ernest Hemingway Home and Museum, this historic Key West property features guest rooms with private balconies and free Wi-Fi.
Duval Street Suite overlooking Duval with parking and pool
Just a 15-minute walk from Mallory Dock and 0.9 miles from Mallory Square, Duval Street Suite overlooking Duval with parking and pool features accommodations in Key West with a garden.
Contra House -Luxury Home With Pool
Just a 14-minute walk from Key West Aquarium and 0.7 miles from Mallory Dock, Contra House -Luxury Home With Pool features accommodations in Key West with a garden.
Conch Cove
Just a 3-minute walk from Duval Street and 600 yards from Ernest Hemingway Home and Museum, Conch Cove features accommodations in Key West with massage services.
Leo's Lodge
Just a 4-minute walk from Ernest Hemingway Home and Museum and 700 yards from Southernmost Point, Leo's Lodge features accommodations in Key West with massage services.
Salvador's Seclusion
Just a 4-minute walk from Ernest Hemingway Home and Museum and 700 yards from Southernmost Point, Salvador's Seclusion features accommodations in Key West with massage services.
Chagall's Corner
Just a 4-minute walk from Ernest Hemingway Home and Museum and 700 yards from Southernmost Point, Chagall's Corner features accommodations in Key West with massage services.
Carey's Corner
Just a 4-minute walk from Ernest Hemingway Home and Museum and 700 yards from Southernmost Point, Carey's Corner features accommodations in Key West with massage services.
