StaysInUSA
Pool · Key West

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.

27 staysUpdated July 7, 2026

Pool · Key West in numbers

27
stays
8.7/10
average guest rating
23 730
traveller reviews
Orchid Key Inn - Adults Only
PoolHot tub

Orchid Key Inn - Adults Only

Key West

4.7Guest score

285 reviews

Check availability
Almond Tree Inn - Adults Only
PoolHot tub

Almond Tree Inn - Adults Only

Key West

4.7Guest score

298 reviews

Check availability
The Mermaid & The Alligator
PoolHot tub

The Mermaid & The Alligator

Key West

4.7Guest score

166 reviews

Check availability
Simonton Court Historic Inn & Cottages
PoolSpa & wellness

Simonton Court Historic Inn & Cottages

Key West

4.6Guest score

993 reviews

Check availability
The Gardens Hotel
PoolPet-friendly

The Gardens Hotel

Key West

4.6Guest score

98 reviews

Check availability
La Te Da - Adult Only, 21 or older
PoolSpa & wellness

La Te Da - Adult Only, 21 or older

Key West

4.6Guest score

179 reviews

Check availability
Douglas House Adult Only
PoolPet-friendly

Douglas House Adult Only

Key West

4.5Guest score

2,291 reviews

Check availability
Island City House
PoolFamily-friendly

Island City House

Key West

4.5Guest score

778 reviews

Check availability
Hyatt Vacation Club at Windward Pointe
PoolHot tub

Hyatt Vacation Club at Windward Pointe

Key West

4.5Guest score

925 reviews

Check availability
The Capitana Key West
PoolBeachfront

The Capitana Key West

Key West

4.5Guest score

2,942 reviews

Check availability
Truman Hotel
PoolBoutique

Truman Hotel

Key West

4.5Guest score

3,466 reviews

Check availability
Eden House
PoolHot tub

Eden House

Key West

4.4Guest score

595 reviews

Check availability
Paradise Inn - Adult Exclusive
PoolHot tub

Paradise Inn - Adult Exclusive

Key West

4.4Guest score

768 reviews

Check availability
Silver Palms Inn & Historic Homes
PoolFamily-friendly

Silver Palms Inn & Historic Homes

Key West

4.4Guest score

3,354 reviews

Check availability
Ella's Cottages - Key West Historic Inns
PoolPet-friendly

Ella's Cottages - Key West Historic Inns

Key West

4.3Guest score

238 reviews

Check availability
Ridley House - Key West Historic Inns
PoolPet-friendly

Ridley House - Key West Historic Inns

Key West

4.3Guest score

248 reviews

Check availability
The Palms Hotel
PoolPet-friendly

The Palms Hotel

Key West

4.3Guest score

2,386 reviews

Check availability
Creme Brulee Suite
PoolPet-friendly

Creme Brulee Suite

Key West

4.3Guest score

27 reviews

Check availability
Coconut Mallory Resort and Marina
PoolHot tub

Coconut Mallory Resort and Marina

Key West

4.3Guest score

135 reviews

Check availability
Lighthouse Hotel - Key West Historic Inns
PoolPet-friendly

Lighthouse Hotel - Key West Historic Inns

Key West

4.2Guest score

630 reviews

Check availability
Winslow's Bungalows - Key West Historic Inns
PoolPet-friendly

Winslow's Bungalows - Key West Historic Inns

Key West

4.2Guest score

1,236 reviews

Check availability
Hampton Inn Key West FL
PoolPet-friendly

Hampton Inn Key West FL

Key West

4.2Guest score

1,240 reviews

Check availability
The Saint Hotel Key West, Autograph Collection, Adult Only
PoolSpa & wellness

The Saint Hotel Key West, Autograph Collection, Adult Only

Key West

4.2Guest score

40 reviews

Check availability
Courtyard by Marriott Key West Waterfront
PoolBeachfront

Courtyard by Marriott Key West Waterfront

Key West

4.1Guest score

372 reviews

Check availability
Classic King Balcony at the James House
PoolPet-friendly

Classic King Balcony at the James House

Key West

4.0Guest score

18 reviews

Check availability
Green Room at the Grand Maloney
PoolSpa & wellness

Green Room at the Grand Maloney

Key West

3.9Guest score

13 reviews

Check availability
Curry House- 3rd Floor, King Bed, & Balcony Room 8
PoolSpa & wellness

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

Key West

3.7Guest score

9 reviews

Check availability

Stays in Key West

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.

Pool · Frequently asked questions

Yes, many hotels in Key West offer heated pools, ensuring a comfortable swimming experience even during cooler periods. Properties like The Palms Hotel, Ella's Cottages, and Lighthouse Hotel are known to feature heated outdoor pools for their guests.

Related searches