Find Key West Hotels with Rooftop Pools

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 3.4 mi (5.5 km) from Mallory Square. 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.

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.

Nestled along the Florida Bay, a short drive from historic Old Town Key West, Florida, this property offers an outdoor pool, casual cafe and a variety of activities.Parrot Key Hotel & Villas is surrounded by lush landscaping and gardens. Guests can go for a swim in one of the 4 outdoor pools, then enjoy a snack from the poolside The Grove Kitchen & Bar. The property is completely nonsmoking.Guests at the Parrot Key Hotel & Villas can spend the day kayaking. After a kayaking trip, guests can relax with an on-site massage or take the complimentary shuttle to the historic Key West old town city center.A 55-inch flat-screen TV and small fridge are featured in each accommodations at the Parrot Key Hotel & Villas. Guests can relax on their private terrace and enjoy views of the ocean and tropical landscape.

Daily Resort Charge includes: Shuttle service to Old Town Key West; two daily in-room bottled waters; beach amenities (chairs, umbrella & cooler); 20% off bicycle rentals for two; 10% off golf cart rentals; arts & crafts for kids. The best of Key West in easy reach We're off Highway 1, three miles from Duval Street and Smathers Beach, and walking distance from restaurants. The Ernest Hemingway House and Old Town can be reached in about 10 minutes, and Mallory Square is only four miles from our door. Enjoy our restaurant, outdoor pool bar, available downtown shuttle service, and 24-hour convenience shop.

Located in Key West (Key West Historic District), Eden House is within a 15-minute walk of Duval Street and Florida Keys Beaches. This hotel is 1.1 mi (1.7 km) from Mallory Square and 1.4 mi (2.2 km) from Southernmost Point. Be sure to enjoy recreational amenities, including an outdoor pool, a hot tub, and bicycles to rent. This Art Deco hotel also features complimentary wireless internet access, concierge services, and gift shops/newsstands. Satisfy your appetite with Mediterranean cuisine at Azur, a restaurant which features a bar/lounge. Dining is also available at the coffee shop/cafe. Wrap up your day with a drink at the poolside bar. Featured amenities include complimentary wired internet access, a computer station, and express check-in. Guests may use a ferry terminal shuttle for a surcharge, and limited parking is available onsite. Make yourself at home in one of the 39 individually decorated guestrooms, featuring microwaves and minibars. Your pillowtop bed comes with down comforters and premium bedding. 32-inch Smart televisions with cable programming provide entertainment, while complimentary wireless internet access keeps you connected. Private bathrooms with showers feature complimentary toiletries and hair dryers.

Caribbean style resort with open air piazza situated on the Gulf of Mexico in the heart of old town Key West. Offering 118 guest rooms with tiled entry foyers, private balconies, ceiling fans, some rooms offer a partial water view. The dress code throughout the island is casual resort wear.

A stay at NYAH Key West - Adults Only places you in the heart of Key West, within a 15-minute walk of Duval Street and Florida Keys Beaches. This guesthouse is 0.8 mi (1.3 km) from Mallory Square and 1.2 mi (1.9 km) from Southernmost Point. Dip into one of the 3 outdoor pools or enjoy other recreational amenities, which include bicycles to rent. Additional amenities at this guesthouse include concierge services and a television in a common area. Grab a bite from the snack bar/deli serving guests of NYAH Key West - Adults Only. Quench your thirst with your favorite drink at the bar/lounge. A complimentary continental breakfast is served daily from 8:00 AM to 10:30 AM. Featured amenities include a 24-hour front desk, multilingual staff, and luggage storage. Make yourself at home in one of the 35 air-conditioned rooms featuring flat-screen televisions. Cable television is provided for your entertainment. Bathrooms have showers and hair dryers.

With a stay at Douglas House - Adults Only, you'll be centrally located in Key West, steps from Duval Street and 5 minutes by foot from Florida Keys Beaches. This guesthouse is 0.3 mi (0.4 km) from South Beach and 0.3 mi (0.4 km) from Southernmost Point. Take advantage of recreation opportunities such as an outdoor pool or take in the view from a terrace and a garden. Additional amenities at this guesthouse include complimentary wireless internet access, concierge services, and a picnic area. The front desk is staffed during limited hours. Make yourself at home in one of the 21 individually decorated guestrooms, featuring microwaves and flat-screen televisions. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Bathrooms have complimentary toiletries and hair dryers. Conveniences include coffee/tea makers and ceiling fans, and housekeeping is provided daily.

When you stay at The Perry Hotel & Marina Key West in Key West, you'll be on the waterfront, within a 5-minute drive of Stock Island Yacht Club & Marina and Key West Golf Club. This hotel is 4.9 mi (7.9 km) from Clarence S. Higgs Memorial Beach Park and 5 mi (8.1 km) from Ernest Hemingway Home and Museum. Dip into one of the 2 outdoor pools or enjoy other recreational amenities including a 24-hour fitness center and bicycles to rent. Additional amenities at this hotel include complimentary wireless internet access, concierge services, and gift shops/newsstands. Satisfy your appetite with seafood at Matt's Stock Island, one of the hotel's 2 restaurants. Wind down with a drink at one of the 2 bars/lounges or 2 poolside bars. Cooked-to-order breakfasts are available daily from 8:00 AM to 11:30 AM for a fee. Featured amenities include dry cleaning/laundry services, a 24-hour front desk, and multilingual staff. Planning an event in Key West? This hotel has 700 square feet (65 square meters) of space consisting of conference space and a meeting room. Self parking (subject to charges) is available onsite. Stay in one of 100 guestrooms featuring flat-screen televisions. Your pillowtop bed comes with premium bedding. Rooms have private furnished balconies or patios. Complimentary wireless internet access keeps you connected, and cable programming is available for your entertainment. Private bathrooms with showers feature designer toiletries and hair dryers.

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.