Compare Resorts with Pools in Key West, FL

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.

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.

Just 500 feet from South Beach and Simonton Beach, Duval Gardens at Southernmost Beach Resort in Key West offers an adults-only escape with convenient access to the city center and a diving club.
This resort features an outdoor swimming pool, an indoor pool, and a heated pool, alongside on-site dining, a bar, room service, and parking, ensuring a comfortable stay with a pool.

Located on 500 feet of private oceanfront in Key West, Florida, this resort offers exclusive access to a property previously featured on MTV's 'The Real World: Key West,' just a short distance from the Ernest Hemingway Home and Museum and Southernmost Point.
This expansive resort boasts 9600 square feet of living space with 10 bedrooms accommodating up to 22 guests, featuring a swimming pool, private boating facilities, and on-site recreational activities like ping pong and kayaking.

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.

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.

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.

Prime beachfront location within the historic Old Town district positions this resort for an unforgettable Key West getaway.
Enjoy a refreshing swim in the resort's swimming pool, complemented by a hot tub, barbecue grills, and proximity within 1 mile of Florida Keys Beaches, Duval Street, and South Beach.

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.

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.