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182 Results
  • Southernmost Beach Resort
    Ranked #1 overall in Key West hotels
    8.2
    Wonderful!
    13 reviews
    Popular withLuxuryFamilies

    This is a huge property. There are two small, unremarkable pools, two tiki bars, which at least look out upon an Atlantic ocean view, and there’s also a private beach, ...

    • Free WiFi
    • Restaurant
    • Fitness Center
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  • Casa Marina, A Waldorf Astoria Resort
    Ranked #2 overall in Key West hotels
    9.3
    Wonderful!
    8 reviews
    Popular withLuxuryHistoryFamilies

    So swanky it hurts, the Casa also has an interesting history. Built in the 1920’s as a WPA project to help drive tourism to Key West, the Casa was briefly ...

    • Free WiFi
    • Restaurant
    • Fitness Center
    • Pets Allowed
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  • Pier House Resort and Spa
    Ranked #3 overall in Key West hotels
    9.1
    Wonderful!
    7 reviews
    Popular withLuxuryNightlifeFamilies

    Pier House Resort & Caribbean Spa is an amazing hotel located in the Key West. This hotel is surrounded by gorgeous ocean views of the Gulf of Mexico, equipped with ...

    • Free WiFi
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
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  • Old Customs House Inn
    Ranked #4 overall in Key West hotels
    7.6
    Pretty good
    9 reviews
    Popular withBusiness

    Booked through expedia...I have booking number and then they cancelled my booking. Tried to call and get it rebooked and now they want an extra $200.00 for the room. Serious ...

    • Free WiFi
    • Restaurant
    ReviewsPhotosAmenitiesMaploadingclose
  • Southernmost House
    Ranked #5 overall in Key West hotels
    8.6
    Wonderful!
    7 reviews
    Popular withHistoryLuxury

    Also a romantic place!

    • Free WiFi
    • Swimming Pool
    • Free Breakfast
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  • The Inn at Key West
    Ranked #6 overall in Key West hotels
    8.7
    Wonderful!
    6 reviews
    Popular withLuxuryFamiliesBusiness

    Not fancy .. But has all basic needs..nice pool and tiki bar to enjoy drinks

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Free Parking
    • Pets Allowed
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  • Parrot Key Hotel and Resort
    Ranked #7 overall in Key West hotels
    8.4
    Wonderful!
    5 reviews

    Quite and relaxing resort! Great pools...

    • Free WiFi
    • Restaurant
    • Fitness Center
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  • Ocean Key Resort & Spa
    Ranked #8 overall in Key West hotels
    8.5
    Wonderful!
    4 reviews
    Popular withLuxuryNightlifeArtsy

    It had been raining on my drive in and the storms were coming in intermittently affecting my stay... though I understand most would be discouraged by the weather however I ...

    • Free WiFi
    • Swimming Pool
    ReviewsPhotosAmenitiesMaploadingclose
  • Knowles House B&B
    Ranked #9 overall in Key West hotels
    10.0
    Exceptional!
    3 reviews
    Popular withTrendstersLGBTQ

    Absolutely BEAUTIFUL!!!! What a gem. We loved our stay here. Great rooms and private pool!!!!

    • Free Parking
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  • Key West Marriott Beachside Hotel
    Ranked #10 overall in Key West hotels
    9.3
    Wonderful!
    3 reviews
    Popular withBusinessLuxuryFamilies

    I liked the room’s clean, cute, bright, and comfortable decor, with fresh, warm sunny colors and a few plush accents. The lobby is sophisticated, but comfortable. The restaurant, Tavern N ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Airport Transfer
    ReviewsPhotosAmenitiesMaploadingclose
  • Hyatt Centric Key West Resort and Spa
    Ranked #11 overall in Key West hotels
    8.7
    Wonderful!
    3 reviews
    Popular withLuxuryFamilies

    Kids love this property, with its winding pathways through shady garden nooks, turtle ponds everywhere, and it’s big, round pool overlooking the Gulf of Mexico. The restaurant, Shor, serves a ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • DoubleTree Resort by Hilton Grand Key - Key West
    Ranked #12 overall in Key West hotels
    6.8
    Pretty good
    5 reviews
    Popular withBusinessLuxuryFamilies

    This was by far an excellent Hilton stay for us. The service was great and all of the staff were friendly and ready to help with anything and everything. The ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Free Parking
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Crowne Plaza Key West La Concha
    Ranked #13 overall in Key West hotels
    8.0
    Wonderful!
    3 reviews
    Popular withBusinessFamiliesHistory

    The La Concha dates back to 1926, and has hosted luminaries like Ernest Hemingway and president Harry Truman. Playwright Tennessee Williams supposedly penned the final draft of A Streetcar Named ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • Sunset Key Cottages
    Ranked #14 overall in Key West hotels
    10.0
    Exceptional!
    2 reviews
    Popular withBusinessOutdoorsyFoodies
    • Restaurant
    • Fitness Center
    ReviewsPhotosAmenitiesMaploadingclose
  • Hyatt Windward Pointe
    Ranked #15 overall in Key West hotels
    10.0
    Exceptional!
    2 reviews
    Popular withLuxuryWellnessFamilies

    Though this is essentially a timeshare property, many of the units are rented out like hotel rooms. Every unit has a lovely porch that catch the ocean breezes. Our unit ...

    • Free Parking
    ReviewsPhotosAmenitiesMaploadingclose
  • The Reach, A Waldorf Astoria Resort
    Ranked #16 overall in Key West hotels
    7.0
    Pretty good
    4 reviews
    Popular withFamiliesLuxury

    Great location right by Duval street. The best part about this place was that it included full access to its sister resort, Casa Marina, which has an awesome breakfast and ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Truman Hotel
    Ranked #17 overall in Key West hotels
    9.0
    Wonderful!
    2 reviews
    Popular withArtsy

    Friendly staff, clean & updated guest rooms, perfect pool & lounge area (especially if you're there with a group). We thoroughly enjoyed our stay! Only 2 blocks from Duval St.

    • Free Parking
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  • Santa Maria Suites
    Ranked #18 overall in Key West hotels
    9.0
    Wonderful!
    2 reviews
    Popular withFoodiesLuxuryArtsy

    I actually gasped upon first view of a Santa Maria suite. They are spacious, well-decorated in a contemporary, sophisticated style with gorgeous Caribbean accents, comfortable, and spotlessly clean. I loved ...

    • Free WiFi
    • Restaurant
    • Fitness Center
    • Free Parking
    ReviewsPhotosAmenitiesMaploadingclose
  • Simonton Court Historic Inn and Cottages
    Ranked #19 overall in Key West hotels
    9.0
    Wonderful!
    2 reviews
    Popular withHistory

    Consists of a B&B and several cottages, it's casual yet tastefully done. The main inn is an old cigar factory. Service is great. The staff who work there are incredibly ...

    • Swimming Pool
    ReviewsPhotosAmenitiesMaploadingclose
  • Cypress House Key West
    Ranked #20 overall in Key West hotels
    9.0
    Wonderful!
    2 reviews
    Popular withHistory

    Great place, very close to Duval Street. New Management, so not sure what they've done.

    • Free WiFi
    • Swimming Pool
    • Free Breakfast
    ReviewsPhotosAmenitiesMaploadingclose
  • Sunrise Suites Resort
    Ranked #21 overall in Key West hotels
    6.7
    Pretty good
    3 reviews
    Popular withFamilies

    My "backyard"

    • Free WiFi
    • Swimming Pool
    • Fitness Center
    • Free Parking
    • Airport Transfer
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • Coral Hammock Key West by KeysCaribbean
    Ranked #22 overall in Key West hotels
    8.0
    Wonderful!
    2 reviews

    Coral Hammock is such a cute place to stay! The town homes are nice and beachy. It's a quiet area as well, except for the daily roster wake up calls!

    • Free Parking
    ReviewsPhotosAmenitiesMaploadingclose
  • Coconut Beach Resort
    Ranked #23 overall in Key West hotels
    9.0
    Wonderful!
    2 reviews
    • Free Parking
    ReviewsPhotosAmenitiesMaploadingclose
  • The Gates Hotel | Key West
    Ranked #24 overall in Key West hotels
    9.0
    Wonderful!
    2 reviews
    Popular withFamilies

    I loved staying here when we were in Key West. It has its own bus that takes you to the more popular, historic side of the island so you can ...

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Free Parking
    • Pets Allowed
    ReviewsPhotosAmenitiesMaploadingclose
  • BEST WESTERN Hibiscus Motel
    Ranked #25 overall in Key West hotels
    7.0
    Pretty good
    2 reviews
    Popular withFamilies

    The Hibiscus doesn’t have much in the way of island charm or luxurious amenities, it’s pretty basically a Best Western. But, hey, there’s a big pool for the kids, a ...

      ReviewsPhotosAmenitiesMaploadingclose
    • Ibis Bay Beach Resort
      Ranked #26 overall in Key West hotels
      10.0
      Exceptional!
      1 review
      Popular withBusiness

      STONE CRAB HEAVEN WHEN IS SEASON !

      • Free WiFi
      • Restaurant
      • Swimming Pool
      • Free Breakfast
      • Free Parking
      ReviewsPhotosAmenitiesMaploadingclose
    • Alexander's Guesthouse
      Ranked #27 overall in Key West hotels
      10.0
      Exceptional!
      1 review
      Popular withLGBTQLuxuryFoodies

      Loved this guesthouse in Key West. Even though we were a straight couple, it was lovely and everyone we met was amazing. Would stay again in a heartbeat.

      • Free Parking
      ReviewsPhotosAmenitiesMaploadingclose
    • Island City House Hotel
      Ranked #28 overall in Key West hotels
      10.0
      Exceptional!
      1 review
      • Free WiFi
      • Swimming Pool
      • Free Parking
      ReviewsPhotosAmenitiesMaploadingclose
    • Eden House
      Ranked #29 overall in Key West hotels
      10.0
      Exceptional!
      1 review
      Popular withLGBTQTrendstersFamilies

      Fun, friendly Eden House is located slightly on the outskirts of the tourist area of Key West (you can rent a bike on the property) and there are several great ...

      • Free WiFi
      • Restaurant
      • Swimming Pool
      • Fitness Center
      • Free Parking
      • Airport Transfer
      ReviewsPhotosAmenitiesMaploadingclose
    • The Saint Hotel Key West
      Ranked #30 overall in Key West hotels
      10.0
      Exceptional!
      1 review
      Popular withNightlifeLuxuryArtsy

      I’d move into this boutique hotel if I could. From the moment you walk up the red-carpeted stairs through the curtains to the porch, open the giant red door and ...

      • Free WiFi
      • Restaurant
      • Swimming Pool
      • Fitness Center
      ReviewsPhotosAmenitiesMaploadingclose
    Key West Hotel Insider
    At the southernmost tip of the United States, at the very end of U.S. Highway 1, lies the tiny Caribbean paradise of Key West, Florida. Just a spit of land surrounded by turquoise waters in the Gulf of Mexico, this island-city lies closer to Havana, Cuba than Miami, Fl. and showcases all the sun-loving good times Caribbean travelers have come to know and love: perfect white sand beaches, charming gardens and historic architecture, colorful shops and vibrant boating communities and of course, vivid sunsets accompanied by fruity cocktails, fresh seafood and a bubbly nightlife. With hotel choices ranging the full gamut between luxury and discount, travelers of all kinds can find the perfect Key West hotel from which to enjoy their stays.

    Luxury Hotels in Key West
    Looking for a bit of timeless luxury on the Florida Keys? You'll find several historic hideaways and modern Key West hotels to choose from. Along the southern edge of the island with more than 1,100 feet of private beach, Casa Marina Key West, a Waldorf Astoria Resort, is listed on the National Register of Historic Places and remains a perfect example of how to comfortably blend Old World Key West hotel charm with contemporary island luxury. Combining historic architectural touches with Florida's modern casual elegance, both the Parrot Key Resort and the Hyatt Key West Resort and Spa are known for their luxurious amenities, superb service, and intimate island settings. Want to be at the heart of the action? Pier House Resort and Spa, the first full-service hotel in Key West, offers island guests a luxurious Key West hotel experience from their waterfront location just on the edge of Old Town.

    Mid-Range and Budget Hotels in Key West
    Although discounted rates and last minute hotel deals can be found at some of the higher end properties, budget-minded travelers looking for cheap Key West hotel alternatives to the luxury island fare will find comfort in seeing the usual cast of budget-friendly characters along with a few interesting Key West boutique hotels and smaller local properties available. Gogobot travelers have found relaxation and comfort in the suites of Sunrise Suites Resort or Villas Key West. Others prefer familiar mid-range options like the Radisson Hotel Key West or the Courtyard by Marriott Key West Waterfront. Value properties such as the Best Western Hibiscus Motel or the Travelodge & Suites Key West are also available.

    Key West Neighborhoods
    At only 2 miles wide and 4 miles long, nothing in Key West is ever very far. Yet even still, it pays to get the lay of the land. Old Town Key West spans a good portion of the island village, covering the western half of the island and centered around Duval Street, with the Key West Cemetery at its heart. Here you'll find picturesque residential streets lined with wooden Victorian homes, including one previously occupied by Ernest Hemingway (now converted into a museum). Historic Seaport lies along the waterfront on the gulf side of the island and encompasses the lower Duval Street area and Mallory Square. This area housed the first shipping docks, warehouses, restaurants and grand homes built on the island and today remains an impressive collections of turn-of the century architecture, much of which has been lovingly restored to its former glory. Here restaurants, bars, retail shops, museums and historic homes are a big draw. But much the same can be said for Downtown Old Town (the tiny section that might even be referred to as "urban," with all of the typically associated modern downtown features) and the boutique, art gallery and restaurant heavy Uptown area. Follow Duval Street to the Atlantic and you'll find Casa Marina, a much sought-after neighborhood featuring beautiful gardens and a variety of mid-century and more modern architectural remnants from Key West's past. Bahama Village offers a truly distinct island flavor (as it was the historic district where Bahamians first moved in when they settled the island in the late1800's) while the Beachside neighborhood is true to its name with a small beach town vibe. Head east to either North or Southside to find the largest collection of Key West resort developments and hotel options. ... Read more

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