Compare Resorts with Pools in Key West, FL

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.

Vacation resort with an excellent rating of 93% based on 20 reviews. You will be in Key West.
Services and facilities include a terrace, a concierge and a food shop. Take advantage of the gym in this resort in Key West.

Just 656 feet from Duval Street, this adults-only resort in Key West offers excellent access to the Southernmost Point, 0.25 miles away, and the Ernest Hemingway Home and Museum, 0.31 miles away, for a serene getaway.
Enjoy an adults-only escape at this Key West resort, featuring a rooftop swimming pool with a sun terrace, an on-site bar with a complimentary happy hour, and bike rentals for exploring the island.

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.

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.

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.

Prime location at the western tip of Key West, Ocean Key Resort & Spa is just 500 feet from Mallory Square and its sunset celebrations, offering a resort experience with a pool.
This resort features a swimming pool, a spa, a fitness center, and offers complimentary Wi-Fi, making it ideal for travelers seeking relaxation and convenience near the historic district.

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.

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.

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.

Directly on the shoreline in Key West, Pier House Resort & Spa offers immediate beach access and a prime location for your getaway.
This resort features a swimming pool and a poolside bar, alongside a spa, fitness center, and on-site restaurant, ensuring a complete vacation experience with a pool.

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.

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.

Directly on a private beach, this historic 1920s resort in Key West is a 7-minute drive from Duval Street and offers two oceanfront swimming pools with direct ocean views.
Enjoy a range of amenities including a spa, fitness center, on-site dining, and convenient access to water sports and nearby attractions like Fort Zachary Taylor Historic State Park.

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.

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.