Find Hotels with an Outdoor Pool in Key West, FL

Discover top Key West attractions

Key West, Florida, is a haven for travelers seeking a laid-back vacation with plenty of opportunities for relaxation. Start your day with a visit to the serene Fort Zachary Taylor Historic State Park, where you can lounge on the beach or take a leisurely stroll through the lush surroundings. Next, explore the picturesque Duval Street, lined with charming boutiques and cafes, perfect for enjoying a refreshing drink or snack after a day of sightseeing. Don't miss the sunset celebration at Mallory Square, where local artists and musicians create a vibrant atmosphere as the sun dips below the horizon. If you're a nature lover, the Key West Butterfly and Nature Conservatory offers a tranquil escape, featuring hundreds of butterflies fluttering amid tropical flowers. For a unique experience, unwind with a spa treatment at one of the luxury resorts along the coast. The area around the southernmost point is particularly enticing, offering a variety of hotels with inviting pools, where you can relax and soak up the sun after a day of exploration. With attentive guest service and a focus on top hotels, you’ll feel pampered while enjoying the best of Key West's laid-back charm.

Find the best hotels with an outdoor pool in Key West

For travelers seeking a refreshing stay in Key West with access to outdoor pools, these hotels offer the perfect blend of relaxation and leisure. Each hotel features a delightful pool experience, ensuring guests can soak up the sun in comfort.

The Perry Hotel & Marina Key West

• Why it's great for poolside lounging: With a stellar guest review rating of 9.4, The Perry Hotel & Marina offers an exceptional outdoor pool experience complete with sun loungers and a vibrant poolside bar, making it ideal for travelers who appreciate a luxurious poolside retreat. This hotel provides a perfect setting to relax while enjoying the beautiful Florida weather.
• Other amenities: Guests can expect an array of features such as a 24-hour fitness center, on-site dining options with alfresco seating, and convenient access to nearby boating and water activities. The hotel also provides housekeeping services, a concierge, and complimentary beach towels to enhance the poolside experience. Marina views and access to areas for kayaking and snorkeling further enrich the guest experience.
• Nearby attractions: Key West Tropical Forest and Botanical Garden - 1.16 miles, Key West Golf Club - 1.67 miles, Stock Island Yacht Club & Marina - 1.48 miles

Winslow's Bungalows - Key West Historic Inns

• Why it's great for poolside lounging: Winslow's Bungalows offers a charming outdoor pool experience, ideal for travelers looking to enjoy a relaxing swim in a picturesque setting. With a review rating of 9.0, this hotel is perfect for those who value a serene poolside environment alongside their Key West adventure.
• Other amenities: This hotel features a garden view restaurant, complimentary breakfasts, and easy access to nearby beaches. Guests can enjoy the convenience of daily housekeeping, a fitness center, and various water activities, including snorkeling and windsurfing. The hotel also provides beach towels and a range of accommodations, including options with private patios and balconies for added comfort.
• Neighborhood: Old Town Key West
• Nearby attractions: Duval Street - 0.24 miles, Saint Mary Star of the Sea - 0.07 miles, Key West Lighthouse and Keeper's Quarters Museum - 0.35 miles

Oceans Edge Key West Resort, Hotel & Marina

• Why it's great for poolside lounging: Oceans Edge Key West Resort, Hotel & Marina is a top choice for pool enthusiasts, an inviting outdoor pool with free cabanas and a poolside bar, perfect for relaxing in style. With an impressive review rating of 8.8, this resort caters to guests looking to enjoy water activities alongside their poolside relaxation.
• Other amenities: Additional offerings include a marina for boating adventures, fitness facilities open 24 hours, and yoga classes on-site. Guests can unwind on furnished balconies, take advantage of nearby golf courses, or indulge in complimentary beach towels. The resort also features various dining options and is conveniently located near water sports like windsurfing and scuba diving.
• Nearby attractions: Key West Tropical Forest and Botanical Garden - 1.77 miles, Key West Golf Club - 1.72 miles, Stock Island Yacht Club & Marina - 0.34 miles

Havana Cabana at Key West

• Why it's great for poolside lounging: The Havana Cabana at Key West is an inviting choice for travelers seeking a vibrant outdoor pool setting. With a review rating of 8.8, this hotel features a beautiful outdoor pool complemented by a poolside bar, offering a lively atmosphere for relaxation and socializing under the sun.
• Other amenities: Guests will appreciate the convenience of an airport shuttle service, a hot tub for extra relaxation, and a restaurant offering poolside dining. The hotel also provides complimentary housekeeping and electric car charging stations. For those looking to explore, a nearby garden and terrace enhance the tropical experience, while self-parking options and air conditioning ensure comfort during the stay.
• Neighborhood: New Town
• Nearby attractions: Florida Keys Beaches - 2.69 miles, Key West Tropical Forest and Botanical Garden - 1.16 miles, Key West Golf Club - 2.05 miles

Southernmost Beach Resort and Guesthouses

• Why it's great for poolside lounging: The Southernmost Beach Resort and Guesthouses is an excellent choice for travelers looking to enjoy the sun by the pool, featuring a well-rated outdoor pool area with a poolside bar and comfortable sun loungers. With a guest review rating of 8.6, this resort offers a relaxing atmosphere perfect for unwinding after a day of exploration.
• Other amenities: Guests can also enjoy a range of features including a full-service spa, daily housekeeping, and access to beautiful beach locations. The resort includes a fitness center, complimentary beach towels, and a historical district location that adds to its charm. Additionally, enjoy on-site dining with ocean views and various water sports nearby such as kayaking and snorkeling.
• Neighborhood: Old Town Key West
• Nearby attractions: Duval Street - 0.03 miles, Key West Butterfly and Nature Conservatory - 0.0 miles, South Beach - 0.05 miles