Best Stays with a Pool in Key West
Key West, a vibrant island city, offers an array of accommodations where a refreshing pool is a central feature. From historic inns to modern resorts, travelers will find numerous options to cool off and relax under the Florida sun. Many properties provide not just a place to swim, but a complete poolside experience, often including breakfast service, sun decks, and even bars. Whether seeking a tranquil adult-only retreat or a family-friendly spot, a stay with a pool in Key West ensures a comfortable and enjoyable escape from the tropical heat, allowing guests to fully embrace the island's laid-back atmosphere.
Pool · Key West in numbers

Orchid Key Inn - Adults Only
Key West
285 reviews
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Almond Tree Inn - Adults Only
Key West
298 reviews
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The Mermaid & The Alligator
Key West
166 reviews
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Simonton Court Historic Inn & Cottages
Key West
993 reviews
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The Gardens Hotel
Key West
98 reviews
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La Te Da - Adult Only, 21 or older
Key West
179 reviews
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Douglas House Adult Only
Key West
2,291 reviews
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Island City House
Key West
778 reviews
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Hyatt Vacation Club at Windward Pointe
Key West
925 reviews
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The Capitana Key West
Key West
2,942 reviews
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Truman Hotel
Key West
3,466 reviews
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Eden House
Key West
595 reviews
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Paradise Inn - Adult Exclusive
Key West
768 reviews
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Silver Palms Inn & Historic Homes
Key West
3,354 reviews
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Ella's Cottages - Key West Historic Inns
Key West
238 reviews
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Ridley House - Key West Historic Inns
Key West
248 reviews
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The Palms Hotel
Key West
2,386 reviews
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Creme Brulee Suite
Key West
27 reviews
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Coconut Mallory Resort and Marina
Key West
135 reviews
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Lighthouse Hotel - Key West Historic Inns
Key West
630 reviews
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Winslow's Bungalows - Key West Historic Inns
Key West
1,236 reviews
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Hampton Inn Key West FL
Key West
1,240 reviews
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The Saint Hotel Key West, Autograph Collection, Adult Only
Key West
40 reviews
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Courtyard by Marriott Key West Waterfront
Key West
372 reviews
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Classic King Balcony at the James House
Key West
18 reviews
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Green Room at the Grand Maloney
Key West
13 reviews
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Curry House- 3rd Floor, King Bed, & Balcony Room 8
Key West
9 reviews
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Many accommodations in Key West with a pool offer a complete resort-like experience. For instance, properties like Coconut Mallory Resort and Marina feature two outdoor pools and hot tubs, alongside apartments with fully-equipped kitchens and private balconies, perfect for extended stays. The Capitana Key West, with its beachfront location, provides a year-round outdoor swimming pool, a terrace, and a fitness center, ensuring guests have everything they need for a relaxing and active vacation.
Travelers will find a variety of pool types to suit their preferences. Several hotels, such as The Palms Hotel and Ella's Cottages, boast heated swimming pools, ideal for cooler evenings or off-season visits. For those seeking an exclusive ambiance, adult-only inns like Paradise Inn and Almond Tree Inn offer outdoor pools with hot tubs and sun decks, often complemented by complimentary wine and cheese hours or daily continental breakfasts served poolside.
Beyond just swimming, the pool areas in Key West hotels often serve as social hubs. Guests can enjoy poolside bars, like the one at Lighthouse Hotel, or grab a bite at a poolside restaurant, as seen at Hampton Inn Key West FL, which also offers ocean views. Many properties also provide additional amenities such as bicycle rentals, picnic areas, and tropical gardens, allowing guests to combine relaxation by the pool with other leisure activities.
Key West exudes a unique blend of bohemian charm, historic allure, and lively entertainment. Its personality is defined by colorful architecture, a relaxed pace, and a strong sense of community. The city is famous for its striking sunsets at Mallory Square, the literary legacy of Ernest Hemingway, and a vibrant nightlife. Beyond the bustling streets, Key West offers serene gardens, beautiful beaches, and a rich maritime history, making it a destination that caters to both adventurers and those seeking tranquility.