Hotels with Pools in Key West
Find the hotels with pools that appeal to you the most
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, 1,177 reviewsFromUS$1291 night, 2 adults
- Scored out of 10, guest rating 9.1Superb - What previous guests thought, 898 reviewsFromUS$2571 night, 2 adults
- Scored out of 10, guest rating 8.9Fabulous - What previous guests thought, 443 reviewsFromUS$2341 night, 2 adults
- Scored out of 10, guest rating 8.3Very good - What previous guests thought, 1,855 reviewsFromUS$1251 night, 2 adults
- Scored out of 10, guest rating 8.2Very good - What previous guests thought, 1,004 reviewsFromUS$1071 night, 2 adults
- Scored out of 10, guest rating 7.9Good - What previous guests thought, 1,914 reviewsFromUS$1251 night, 2 adults
- Scored out of 10, guest rating 9.1Superb - What previous guests thought, 2,561 reviewsFromUS$2061 night, 2 adults
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 301 reviewsFromUS$2581 night, 2 adults
- Scored out of 10, guest rating 7.4Good - What previous guests thought, 972 reviewsFromUS$1461 night, 2 adults
- Scored out of 10, guest rating 8.0Very good - What previous guests thought, 295 reviewsFromUS$1701 night, 2 adults
- Scored out of 10, guest rating 8.4Very good - What previous guests thought, 2,348 reviewsFromUS$1591 night, 2 adults
- Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 1,242 reviewsFromUS$2391 night, 2 adults
- Scored out of 10, guest rating 7.6Good - What previous guests thought, 1,108 reviewsFromUS$1751 night, 2 adults
- Scored out of 10, guest rating 7.9Good - What previous guests thought, 1,355 reviewsFromUS$1791 night, 2 adults
- Scored out of 10, guest rating 8.3Very good - What previous guests thought, 525 reviewsFromUS$2501 night, 2 adults
- Scored out of 10, guest rating 8.5Very good - What previous guests thought, 1,197 reviewsFromUS$1491 night, 2 adults
- Scored out of 10, guest rating 9.4Superb - What previous guests thought, 302 reviewsFromUS$2411 night, 2 adults
- Scored out of 10, guest rating 9.1Superb - What previous guests thought, 1,051 reviewsFromUS$2791 night, 2 adults
- Scored out of 10, guest rating 8.6Fabulous - What previous guests thought, 632 reviewsFromUS$2271 night, 2 adults
- Scored out of 10, guest rating 9.3Superb - What previous guests thought, 676 reviewsFromUS$2791 night, 2 adults
Filter by:
The Capitana Key West
Situated in Key West, 2.1 km from Smathers Beach, The Capitana Key West features accommodation with an outdoor swimming pool, free private parking, a fitness centre 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 110 metres from the Southernmost Point and 73 metres 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 500 metres 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 200 metres 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
Boasting an outdoor swimming pool, a garden as well as a shared lounge, The Mermaid & The Alligator is situated in the centre of Key West, less than 1 km from South Beach.
Hyatt Vacation Club at Windward Pointe
This Hyatt Windward Pointe is situated in Key West, 5.7 km from the Southernmost Point, and boasts a year-round outdoor pool and hot tub. A fully equipped kitchen is provided in every apartment.
Key West Villas
Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.
The best hotels with pools in Key West
Check out our pick of great hotels with pools in Key West
Filter by:
The Capitana Key West
Situated in Key West, 2.1 km from Smathers Beach, The Capitana Key West features accommodation with an outdoor swimming pool, free private parking, a fitness centre 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 110 metres from the Southernmost Point and 73 metres 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 500 metres 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 200 metres 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
Boasting an outdoor swimming pool, a garden as well as a shared lounge, The Mermaid & The Alligator is situated in the centre of Key West, less than 1 km from South Beach.
Hyatt Vacation Club at Windward Pointe
This Hyatt Windward Pointe is situated in Key West, 5.7 km from the Southernmost Point, and boasts a year-round outdoor pool and hot tub. A fully equipped kitchen is provided in every apartment.
Key West Villas
Located in the heart of historic Key West, guests will be 1 minutes’ walk from Duval Street. A heated pool, daily continental breakfast, and free WiFi are provided.
Looking for a hotel with pools?
Most booked hotels with pools in Key West and surroundings 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
Save money on pools in Key West and nearby – budget options available
Lighthouse Suites Collection
Offering free WiFi and sea views, Lighthouse Suites Collection is an accommodation set in the heart of Key West, just 600 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum.
Key West Light Suite
Offering free WiFi and sea views, Key West Light Suite is an accommodation situated right in the heart of Key West, just 700 metres from South Beach and 200 metres from Ernest Hemingway Home and...
Wicker Guesthouse
Located one block from the Ernest Hemingway House and Museum in Key West, Florida, this guesthouse offers a large tropical garden and an outdoor pool. Rooms feature free Wi-Fi.
BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub
Set in the centre of Key West, 700 metres from South Beach and 200 metres from Ernest Hemingway Home and Museum, BachelorPARTY HQ for 16-Feet to Duval-Pool-Hot tub offers free WiFi, a garden and air...
Old Town Garden Villas - Andros Suite
Old Town Garden Villas - Andros Suite has a patio and is located in Key West, within just 400 metres of Duval Street and 300 metres of Ernest Hemingway Home and Museum.
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.
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 has a patio and is located in Key West, within just 500 metres of Duval Street and 300 metres of Ernest Hemingway Home and Museum.
Great access to the city centre. Check these hotels with pools in Key West and nearby
Casa Key West-Pool & Free Parking
Right in the heart of Key West, situated within a short distance of South Beach and Ernest Hemingway Home and Museum, Casa Key West-Pool & Free Parking offers free WiFi, air conditioning and household...
New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool
Located in the centre of Key West, 600 metres from South Beach and 500 metres from Ernest Hemingway Home and Museum, New Casa Caribe by Brightwild- Two-Story Condo Rooftop Pool offers free WiFi and...
Set in the centre of Key West, 700 metres from South Beach and 300 metres from Duval Street, Duval Street Suite w kitchen and shared heated pool offers free WiFi, a garden and air conditioning.
Set in the centre of Key West, 700 metres from South Beach and 300 metres from Duval Street, Duval Street Suite overlooking Duval w parking and pool offers free WiFi, a garden and air conditioning.
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.
Enjoy breakfast in Key West and nearby
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.
The Conch House Heritage Inn
This adult-only Conch House Heritage Inn offers accommodation in Key West with breakfast included and complimentary mimosas.
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.
Located in Key West, Florida, Winslow's Bungalows features 3 swimming pools, free WiFi access, and complimentary continental breakfast.
Southernmost Inn Adult Exclusive
This adults only Key West resort is 1 minutes' walk from Duval Street and 5 minutes' walk from the Atlantic Ocean. It features 2 heated outdoor pools, a hot tub and continental breakfast.
Pegasus International Hotel
This Art Deco hotel in downtown Key West has a large pool-side sun terrace and rooms with a flat-screen TV. All guest rooms at Pegasus International Hotel are equipped with free Wi-Fi.
Silver Palms Inn
Silver Palms Inn, located in historic Key West, has an outdoor pool and is a 9-minute walk from the Ernest Hemingway Museum. Guest rooms offer private balconies and 40-inch flat-screen TVs.
