Compare Resorts with Pools in Key West, FL

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.

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.

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.

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.

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.

This resort is located in the historic Old Town Key West, just 500 feet from the Ernest Hemingway Home and Museum and Southernmost Point.
Offering 2080 square feet of living space, this 4-bedroom, 3-bathroom Caribbean-style villa accommodates up to 8 guests and features a private lagoon-style swimming pool with a waterfall, a tropical garden, and off-street parking.

Oceanfront suites with private screened-in balconies offer a tranquil escape at Hyatt Vacation Club At Beach House, located 1.9 miles from Key West International Airport and 4 miles from Duval Street.
This resort boasts spacious suites with full kitchens, a swimming pool, and convenient access to water sports, making it an ideal choice for a Key West getaway with a pool.

Galleon Resort and Marina, a resort in Key West, is located on a private Gulf of Mexico beach, just a 5-minute walk from the Key West Shipwreck Museum and Mallory Square.
This resort offers a fantastic outdoor swimming pool and hot tub, along with on-site water sports facilities and bicycle rentals for guests seeking a fun-filled getaway with a pool.

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.

Just 500 feet from Duval Street in Key West's Old Town Historic district, this resort offers a prime location near Mallory Square and gourmet shops.
This expansive 2390 sq ft resort, perfect for up to 14 guests, features two private swimming pools, lush tropical gardens with a waterfall, and offers a secluded retreat with ample indoor/outdoor living space.

Enjoy a resort stay in Key West, just a short distance from its renowned galleries and restaurants, and close to landmarks like the Ernest Hemingway Home and Museum and Southernmost Point.
This resort offers a swimming pool and features a sandy beach, along with two bedrooms and two bathrooms accommodating up to six guests.

Located in Key West's Northside Resort neighborhood within Key Cove Landings, this resort offers a private waterfront retreat, just a short drive from downtown Old Town and within walking distance to grocery stores and the island's largest shopping center.
This spacious 2690 sq ft resort features four bedrooms, luxurious interiors, and outdoor living spaces, making it an ideal pool getaway with a private heated swimming pool and dip area for ultimate relaxation.

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.

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.

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.

Oceanfront suites with private screened-in balconies offer a tranquil escape at Hyatt Vacation Club At Beach House, located 1.9 miles from Key West International Airport and 4 miles from Duval Street.
This resort boasts spacious suites with full kitchens, a swimming pool, and convenient access to water sports, making it an ideal choice for a Key West getaway with a pool.