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Hotels in Key West
80 Hotels
Margaritaville Key West Resort & Marina
245 Front Street

This 178-room waterfront hotel in Old Town Key West is a real resort, with dozens of features, including boat rentals, shops, a fitness center, and a marina. However, it’s not quite up to the standards of other luxury properties, with somewhat bare contemporary rooms, cramped bathrooms, a pool that's a bit small for the size of the hotel, and a location right by a busy and noisy cruise ship dock. There’s nothing really bad about the resort, but there’s nothing outstanding either -- it’s just slightly better than adequate. Also, some of the amenities, like the spa, are at the sister property on Sunset Key, a 7-minute boat ride from the hotel.

Sunset Key Cottages
245 Front Street

Located along a lovely beach, the 40-room Sunset Key Cottages resort caters to the upscale traveler with elegant, homey cottages and high-end amenities. It is located on Sunset Key, a residential island off Key West, and is affiliated with the Margaritaville Key West Resort and Marina, with which it shares some features. The hotel itself has wonderful amenities, including a lovely zero-entry pool, a gorgeous (though somewhat rocky) beach with palm trees and clear, calm waters, and a pleasant spa. There is 24-hour free shuttle service to Key West, but the resort’s location, though idyllic and exclusive, might be somewhat inconvenient for travelers who want to be close to shops and restaurants. Couples seeking something a tad cheaper may want to compare rates at Le Mer Hotel and Dewey House at Southernmost Beach Resort.

Ocean Key Resort & Spa
0 Duval Street

The 100-room Ocean Key Resort is an upscale waterfront property with an elegant atmosphere that captures the artistic whimsy of Key West. Contemporary rooms have large, comfortable beds, whirlpool tubs, and minibars, plus feature a cheerful, island-flavored design. There are two restaurants on-site, including the classy Hot Tin Roof. Outside, guests can grab a colorful table on the pier. The spa, fitness room, and small pool with a hot tub make this a lovely choice for relaxing when not exploring the island. However, extra expenses -- resort fees, mandatory valet parking, and breakfast, for example -- on top of high-end rates can quickly price some out of this hotel. Try Casa Marina Resort by Waldorf Astoria for a less exorbitant rate at a nonetheless grand resort. 

The Saint Hotel Key West, Autograph Collection
417 Eaton St

The three-and-a-half-pearl Saint Hotel Key West emits a sexy vibe with its "play naughty, sleep saintly" slogan. Situated next to the buzzing nightlife on Duval Street and within easy walking distance of top sights, the hotel's location is one of its key features. Also a standout are the pretty pool, eclectic decor, well-reviewed fare at the bar, and in-room massage offerings. The 36 rooms have stylish decor, modern amenities, and comfy beds, but many are tiny, dark, and have see-through showers. or enjoy a getaway with a significant other will be hard-pressed to find a better fit. It's worth comparing rates with the nearby Almond Tree Inn, which has brighter rooms and offers a free breakfast.

The Southernmost Inn, Key West
525 United St

The 38-room, lower-middle-range Southernmost Inn was converted from a late-1800s cigar factory and renovated in 2014. The adult-only inn draws many couples, and feels like a classic Key West bed-and-breakfast, with a welcoming porch, plentiful outdoor space for lazy days, antique furniture, and two pretty swimming pools with palm-shaded patios. Free breakfast includes Starbucks coffee, and chocolates are left on pillows. Guest rooms are spotless and minimally decorated, with flat-screen TVs, colonial wooden blinds, and wood floors. Walls are somewhat thin, and Wi-Fi strength varies at this no-frills -- but not bare-bones -- property that offers a simple and pretty bed-and-breakfast near the best sights in town. Guests traveling with children or wanting a livelier poolside scene could try Southernmost Hotel. 

Crowne Plaza Key West La Concha
430 Duval Street

The 160-room Crowne Plaza Hotel Key West - La Concha is a historic landmark dating back to 1926, but this upper-middle-range property now appears has plenty of glitzy modern appeal. Rooms have vintage Caribbean-chic decor and feature flat-screen TVs, mini-fridges, and coffeemakers, and some have balconies overlooking the hotel's prime Duval Street location. The on-site restaurant serves all meals, and there's a hip wine bar in the lobby. There's also a bar by the small outdoor pool. Previous guests may miss the popular rooftop bar, which has been replaced by a spa and fitness center. Travelers who would prefer to be a bit outside the action and closer to the water could check out the Key West Marriott Beachside Hotel

Island House
1129 Fleming St

Located in historic Key West, Island House is a 34-room boutique designed exclusively for gay men. Many restaurants and tourist attractions along Duval Street are located within easy walking distance. Rooms are stylish, if small, and some have showers with multiple shower heads. The outdoor pool and hot tub is surrounded by lounge chairs and lush foliage. The entire hotel (except the gym) is clothing optional and the staff plans on- and off-site activities specifically for gay men.

Southernmost Beach Resort
1319 Duval Street

The 124-room Southernmost on the Beach is an upscale property located on the beach in southern Key West. Spacious rooms offer a host of modern comforts including Nespresso machines, and many have lovely, private balconies, some with spectacular ocean views. Highlights here include the beautiful, sandy beach with a private sunbathing pier and hammocks strung between palm trees, as well as the outdoor pool with two poolside bars. Other features include a cafe open for all meals, a small fitness center, and beachside spa services. The location near Duval Street means restaurants, bars, shops, and several attractions are within walking distance. The hotel's neighboring sister property, the Southernmost Hotel, often has cheaper rates, and its guests get access to the features here.

Almond Tree Inn
512 Truman Avenue

The Almond Tree Inn is an upper-middle-range boutique, offering 22 stylish rooms decorated in yellow, green, and white tropical decor. It's a great value compared to other nearby hotels, providing both free breakfast and a free happy hour. Property features include a serene pool courtyard with waterfalls and lush landscaping, and the location is in the heart of Old Town Key West, within walking distance of Duval Street.

Coconut Mallory Resort And Marina
1445 S Roosevelt Blvd

The mid-range Coconut Mallory Resort and Marina is an affordable condominium-style property that’s geared toward families with a location that -- albeit removed from the excitement of Key West -- offers direct marina access and 18 boat slips. The 34-room resort has two outdoor pools, a hot tub, barbecue grills, poolside hammocks, and a waterfront bar. Homey and spacious one- and two-bedroom units have flat-screen TVs, kitchenettes or kitchens, and balconies or patios. Interior decor, however, is occasionally dated and weathered. Wi-Fi, coffee, and outdoor parking are all free.