Key West Hotels with Rooftop Pools

A stay at Silver Palms Inn & Historic Homes places you in the heart of Key West, within a 10-minute walk of Duval Street and Ernest Hemingway Home and Museum. This hotel is 0.7 mi (1 km) from Florida Keys Beaches and 0.7 mi (1.2 km) from South Beach. Take advantage of recreation opportunities including an outdoor pool and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and a television in a common area. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage. Make yourself at home in one of the 50 individually furnished guestrooms, featuring refrigerators and LCD televisions. Your pillowtop bed comes with down comforters and Egyptian cotton sheets. Complimentary wired and wireless internet access keeps you connected, while iPod docking stations help you enjoy your music in the comfort of your room. Bathrooms have showers and hair dryers.

With a stay at Opal Key Resort & Marina, Key West, you'll be centrally located in Key West, steps from Mallory Square and 3 minutes by foot from Duval Street. This hotel is 0.3 mi (0.5 km) from Florida Keys Beaches and 0.7 mi (1.1 km) from Ernest Hemingway Home and Museum. Take advantage of recreational opportunities offered, including an outdoor pool, a hot tub, and a 24-hour fitness center. This hotel also features concierge services and a banquet hall. At Opal Key Resort & Marina, Key West, enjoy a satisfying meal at the restaurant. Relax with a refreshing drink from the poolside bar or one of the 3 bars/lounges. Cooked-to-order breakfasts are available daily from 7:00 AM to 10:00 AM for a fee. Featured amenities include a 24-hour business center, dry cleaning/laundry services, and a 24-hour front desk. This hotel has 11 meeting rooms available for events. Self parking (subject to charges) is available onsite. Make yourself at home in one of the 178 air-conditioned rooms featuring flat-screen televisions. Cable television is provided for your entertainment. Bathrooms feature bathtubs or showers with rainfall showerheads and complimentary toiletries. Conveniences include safes and desks, as well as phones with free local calls.

Located in Key West (Key West Historic District), Westwinds Inn is within a 15-minute walk of Duval Street and Florida Keys Beaches. This hotel is 0.7 mi (1.2 km) from Mallory Square and 1.3 mi (2 km) from Southernmost Point. Take in the views from a garden and make use of amenities such as complimentary wireless internet access and concierge services. Additional features at this hotel include barbecue grills and a vending machine. Mingle with other guests at the complimentary reception, held on select days. A complimentary continental breakfast is served daily from 8:00 AM to 10:00 AM. Featured amenities include complimentary newspapers in the lobby, luggage storage, and laundry facilities. Make yourself at home in one of the 26 air-conditioned rooms featuring flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers.

Winslows Bungalows

Minutes from the Key West Historic Seaport Fitch Lodge welcomes on-the-go explorers to authentic conch-house lodging in a neighborhood setting. Return from reef diving or deep-sea fishing to informal bohemian accommodations and a refreshing pool.

Unlock a New Treasure at a Gem Among Florida Keys Resorts. Poised on the pristine waterfront of Key West's historic seaport, The Marker is the only newly built hotel to grace Old Town Key West in over 20 years, seamlessly blending the timeless elegance of classic Florida Keys resorts with an understated air of modern glamour. Featuring 96 state-of-the-art rooms on two lush acres of tropical landscaped seclusion, The Marker is a tropical oasis set within a vibrant, free spirited paradise filled with sun, surf, art and culture. Resort Fee of $45.00 /per night will be charged to the guest upon Check-in.

With a stay at Authors of Key West Guest House in Key West (Key West Historic District), you'll be within a 5-minute drive of Key West Lighthouse and Keeper's Quarters Museum and Duval Street. This bed & breakfast is 1 mi (1.5 km) from Ernest Hemingway Home and Museum and 1 mi (1.6 km) from Clarence S. Higgs Memorial Beach Park. Enjoy recreation amenities such as an outdoor pool or take in the view from a terrace. Additional amenities at this bed & breakfast include complimentary wireless internet access, concierge services, and a picnic area. A complimentary continental breakfast is served daily from 8:00 AM to 10:30 AM. Featured amenities include complimentary newspapers in the lobby and a water dispenser. Make yourself at home in one of the 13 air-conditioned rooms featuring refrigerators. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms feature showers, complimentary toiletries, and hair dryers. Conveniences include irons/ironing boards, and housekeeping is provided daily.

With a stay at Hyatt Vacation Club at Windward Pointe, Key West in Key West, you'll be near the airport, within a 15-minute walk of Fort East Martello Museum and Gallery and Key West Art and Historical Society. This hotel is 1.2 mi (1.9 km) from Smathers Beach and 3.5 mi (5.6 km) from Duval Street. Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and bicycles to rent. This hotel also features complimentary wireless internet access, concierge services, and babysitting (surcharge). You can enjoy a meal at the restaurant serving the guests of Hyatt Vacation Club at Windward Pointe, Key West, or stop in at the snack bar/deli. Featured amenities include a safe deposit box at the front desk and an elevator. Free self parking is available onsite. Make yourself at home in one of the 93 guestrooms, featuring kitchens with refrigerators and stovetops. Rooms have private balconies. Complimentary wireless internet access keeps you connected, and DVD players are provided for your entertainment. Bathrooms with separate bathtubs and showers feature jetted bathtubs and complimentary toiletries.

Daily Resort Charge includes: WiFi: poolside concierge services: activities including volleyball & table tennis: beach chairs, umbrellas & hammocks: access to amenities at Casa Marina and The Reach: chilled fruit-infused spring water: pool hydration stations. Listed in the National Register for Historic Places, Casa Marina Key West, Curio Collection by Hilton, is a historic landmark with Old Town Key West elegance. Conceived over 100 years ago by the railroad magnate Henry Flagler, the hotel was designed to replicate the arches of Flagler's pioneering Overseas railway. The hotel opened on New Year's Eve, 1920. Nestled along the southern edge of the island on more than 1,100 feet of Key West's largest private beach, the 311 room Casa Marina is in proximity to the vibrant spots of Duval Street and rich history of Old Town. Offering the finest in resort activities, along with a dedicated beach and pool concierge, guests enjoy experiences from sand sculpting workshops led by the award-winning resident sculptor to ocean sports including jet-ski tours and deep-sea fishing charters. Key West's freshest ingredients are featured on Sun Sun Bar and Grill's island-style menu for a poolside bite or beachside dinner. For the ultimate in relaxation, Spa al Mare offers relaxing treatments matched with uncompromisingly pure products.

With a stay at Havana Cabana at Key West in Key West (New Town), you'll be a 5-minute drive from Florida Keys Beaches and 6 minutes from Duval Street. This hotel is 3.2 mi (5.1 km) from Southernmost Point and 3 mi (4.8 km) from Smathers Beach. Enjoy a range of recreational amenities, including an outdoor pool, a hot tub, and bicycles to rent. Additional features at this hotel include complimentary wireless internet access, concierge services, and complimentary use of a nearby fitness facility. You can enjoy a meal at Floridita Food Truck serving the guests of Havana Cabana at Key West , or stop in at the snack bar/deli. Relax with your favorite drink at the bar/lounge or the poolside bar. Cooked-to-order breakfasts are available daily from 7:00 AM to 10 AM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Free self parking is available onsite. Make yourself at home in one of the 106 individually decorated guestrooms, featuring refrigerators and microwaves. Flat-screen televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms with bathtubs or showers feature complimentary toiletries and hair dryers. Conveniences include safes and desks, and housekeeping is provided daily.