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

    I love this place. If you want to stay next to the beach. Stay at this hotel! Family&kids are welcome

    • 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

    The Casa Marina is luxurious and elegant in every way. The spacious open lobby lined with couches is just a taste of the comfort each room offers. Spend the day ...

    • 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 has a spacious property on the Gulf of Mexico, with a resident pet parrot, a turtle pond, and the famous Chart Room Bar, a former Jimmy Buffet hang ...

    • 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

    Seriously, no joke, this place was tiny. Two rows of stools, about three on each side and some standing room in the middle. Barkeep had to use coolers... not even ...

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

    Architecturally, this place looks like nowhere else in Key West, and is considered a landmark building. Built in 1896 as a private resident for a judge, it became notorious Cuban ...

    • 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

    Nice, that's still I'm gonna say

    • 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
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  • Knowles House B&B
    Ranked #9 overall in Key West hotels
    10.0
    Exceptional!
    3 reviews
    Popular withHipstersLGBTQ

    Cozy, fun, lovely nice hosts! I feel like we're staying with family!

    • 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
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  • Hyatt Centric Key West Resort and Spa
    Ranked #11 overall in Key West hotels
    8.7
    Wonderful!
    3 reviews
    Popular withLuxuryFamilies

    Perfect location right on Mallory Square. Nice rooms and gorgeous views. The pool is a perfect size with both sun and shade. The bartender made the best mojitos I've had ...

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

    What a gorgeous property, the lush grounds were full of palm trees and exotic landscape surround the pool area.

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

    We had a great time at The Reach. The private beach was amazing, it's quite close to Duval street. We only stayed a couple of nights but wished we could ...

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

    Art-deco, South Beach coolness is written all over this spanking-new little boutique hotel. The accommodations aren’t big, but they are fun and filled with flair, such as zebra print rugs ...

    • 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
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  • Simonton Court Historic Inn and Cottages
    Ranked #19 overall in Key West hotels
    9.0
    Wonderful!
    2 reviews
    Popular withHistory

    Built in 1880, the inn was a cigar-making factory, and the cottages housed cigar-makers. The brick walkway which spans the lush property was once an actual lane. The cottages are ...

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

    Cypress house sits a block away from the action on downtown Duval Street and within bike riding distance of Fort Zachary Taylor State Park. Built in 1888, Cypress House was ...

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

    When I stayed here with family, our condo had two separate bedrooms and baths, as well as a full kitchen, which is really nice considering the price (there were 3 ...

    • 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
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  • 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 withLGBTQHipstersFamilies

      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

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