Compare Resorts with Pools in Key West, FL

Located in Key West's Old Town, this resort offers a private beachfront, placing you a 15-minute walk from Duval Street and a 10-minute walk from the Earnest Hemingway Museum.
Enjoy your stay at The Reach Key West, Curio Collection by Hilton, a resort with a pool, private balconies, and on-site activities like scuba diving and deep-sea fishing, with access to a full-service spa at a sister property.

Beachside Resort & Residences offers direct access to a private beach with Gulf of Mexico views, located less than 1.2 miles from Key West Airport and providing a free shuttle to Key West city center.
This resort features a swimming pool and a water view fitness center, with accommodations including flat-screen TVs, Bluetooth speakers, and options for full kitchens and balconies, perfect for a Key West getaway with a pool.

Located in the Key West Historic District, this resort is less than 1 mile from Mallory Square and the Florida Keys National Marine Sanctuary, and just over 1 mile from Southernmost Point.
Enjoy three outdoor swimming pools at this resort with a pool, offering a refreshing escape with an onsite restaurant, bar, fitness center, and complimentary WiFi.

Perfectly situated in Key West's Old Town, this resort offers direct access to a private beach and is just a 1-minute walk from the Duval Street entertainment district, with the historic Hemingway Home and Museum only a 5-minute drive away.
This resort features a swimming pool with waterfront views and provides a full-service spa, on-site dining at One Duval, and easy access to water sports for a complete getaway.

Along Florida Bay, this resort is a short drive from the historic Old Town Key West, offering direct access to kayaking activities and four outdoor swimming pools.
Enjoy poolside snacks at the on-site casual cafe, The Grove Kitchen & Bar, and relax with on-site massage services, all part of a resort fee that includes premium WiFi and shuttle service to the city center.

Just 1 mile from Key West International Airport and Smathers Beach, the Doubletree By Hilton Grand Key Resort offers convenient access to Old Town Key West and Duval Street.
This resort features a swimming pool with outdoor cabanas and a poolside tiki bar, plus a fitness center and on-site dining.

Blue Flamingo Resort Key West is located 3 miles from the city center, near the Key West Tropical Forest and Botanical Garden and Lower Keys Medical Center.
This resort offers access to four swimming pools, including indoor and outdoor options, and features a fitness center, children's playroom, and a tour assistance desk, ensuring a complete stay with a pool.

Directly located at the Stock Island Marina, The Perry Hotel & Marina Key West offers exceptional waterfront views and marina access, just one bridge away from Key West's attractions and 5 miles from Duval Street.
This resort boasts luxury accommodations with private balconies, two on-site sea-to-table restaurants, and two waterfront swimming pools, perfect for a relaxing getaway with a pool.

Enjoy a waterfront resort experience in Key West, just a 3-minute walk from Duval Street's dining and nightlife.
This resort features a swimming pool and offers on-site spa services, water activities like scuba diving and snorkeling, and two distinct dining options.

Just a block from Duval Street and the Atlantic Ocean, Santa Maria Suites Resort in Key West offers an excellent location, placing you an 11-minute walk from the Ernest Hemingway House.
This all-suite resort features two outdoor heated swimming pools set in lush gardens, providing a perfect escape with complimentary happy hour and in-suite laundry facilities.

Prime beachfront in Old Town Key West, this resort is steps from South Beach and Southernmost Point, and 1.3 miles from Fort Zachary Taylor Historic State Park.
Guests can enjoy three outdoor swimming pools at this resort, offering a perfect getaway with a pool for relaxation and easy access to Old Town attractions.

Directly on Duval Street in Old Town Key West, this resort puts you steps from dining and entertainment, offering a prime location for exploring the historic district.
This resort features a swimming pool and modern amenities including an on-site restaurant and fitness center, perfect for a getaway with a pool.