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381 Results
  • Cheeca Lodge & Spa
    Ranked #1 overall in Islamorada hotels
    9.511 reviews
    Popular withLuxuryWellnessAdventure
    • Free WiFi
    • Fitness Center
    • Free Parking
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  • Little Palm Island Resort & Spa
    Ranked #1 overall in Little Torch Key hotels
    10.010 reviews
    Popular withLuxuryFoodiesOutdoorsy

    great lunch

    • Free WiFi
    • Restaurant
    • Swimming Pool
    • Fitness Center
    • Free Parking
    • Airport Transfer
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  • Southernmost Beach Resort
    Ranked #1 overall in Key West hotels
    8.213 reviews
    Popular withLuxuryFamilies
    • Free WiFi
    • Restaurant
    • Fitness Center
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  • Ocean View Inn and Sports Pub
    Ranked #2 overall in Islamorada hotels
    9.69 reviews
    Popular withOutdoorsyFoodiesFamilies

    Funky Local sports bar with better than bar food on the bay. Playground for the kids and they let patrons use the wonderful pool.

    • Restaurant
    • Free Parking
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  • Casa Marina, A Waldorf Astoria Resort
    Ranked #2 overall in Key West hotels
    9.38 reviews
    Popular withLuxuryHistoryFamilies

    Haven't stayed in the hotel. Just crashed the pool. Private beach and two pools are what attracted me here. Despite not being guests in the hotel, me and my friends ...

    • Free WiFi
    • Restaurant
    • Fitness Center
    • Pets Allowed
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  • Pier House Resort and Spa
    Ranked #3 overall in Key West hotels
    9.17 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
    7.69 reviews
    Popular withBusiness

    Not fancy, no frills, not even walls to separate the bedroom from the living room, but the front door is literally on Duval Street, so who can complain. Steps to ...

    • Free WiFi
    • Restaurant
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  • Islander Resort, a Guy Harvey Outpost
    Ranked #3 overall in Islamorada hotels
    10.06 reviews
    Popular withOutdoorsyAdventureFamilies

    Great little beach side Resort. It has a huge beach with lots of fun activities, a nice pool and Hot tub (although the pool water is too warm) and a ...

    • Free WiFi
    • Restaurant
    • Fitness Center
    • Free Parking
    • Pets Allowed
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  • Southernmost House
    Ranked #5 overall in Key West hotels
    8.67 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
    8.76 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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  • Hilton Key Largo Resort
    Ranked #1 overall in Key Largo hotels
    8.45 reviews
    Popular withAdventureOutdoorsyFamilies

    This is the Killer Colada which was tasty! I had more than a few :) The hotel was great with lots of activities and a relaxing beautiful atmosphere!

    • Free WiFi
    • Fitness Center
    • Free Parking
    • Pets Allowed
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  • Parrot Key Hotel and Resort
    Ranked #7 overall in Key West hotels
    8.45 reviews

    Loved this place! Nice clean cozy room. Vibrant decor. Large bathroom. Comfy beds & linens. Great back patio. Several great pools to choose from. Very good cocktails pool side. If ...

    • Free WiFi
    • Restaurant
    • Fitness Center
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  • Simonton Court Historic Inn and Cottages
    Ranked #21 overall in Key West hotels
    9.02 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
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  • Ocean Key Resort & Spa
    Ranked #8 overall in Key West hotels
    8.54 reviews
    Popular withLuxuryNightlifeArtsy

    Ocean Key, where the Gulf of Mexico meets Key West’s main tourist drag, Duval Street, is as far downtown as you can go. The area itself is overwhelmingly touristy, so ...

    • Free WiFi
    • Swimming Pool
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  • Smugglers Cove Resort and Marina
    Ranked #4 overall in Islamorada hotels
    9.33 reviews
    Popular withOutdoorsyAdventureFamilies

    They RENT fishing poles and have private Fishing Charters! RESTAURANT MARINA BANDS/LIVE Music RETAIL STORE LOCATION FISHING CHARTERS FISHING TOURNAMENTS BANANA HUT ECO TOUR BOAT RENTAL WEDDINGS SPECIAL EVENTS SCUBA/SNORKELING ...

    • Free WiFi
    • Restaurant
    • Free Parking
    • Pets Allowed
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  • The Reach, A Waldorf Astoria Resort
    Ranked #18 overall in Key West hotels
    7.04 reviews
    Popular withLuxuryFamilies

    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
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  • Bahia Honda State Park
    Ranked #1 overall in Marathon hotels
    10.03 reviews
    Popular withHistoryOutdoorsyAdventure

    Listed as one of the most beautiful beaches in the nation.

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    • Sunset Key Cottages
      Ranked #9 overall in Key West hotels
      10.03 reviews
      Popular withLuxuryWellnessBusiness
      • Restaurant
      • Fitness Center
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    • Tranquility Bay Beachfront Hotel and Resort
      Ranked #2 overall in Marathon hotels
      10.03 reviews
      Popular withFamiliesWellnessOutdoorsy
      • Free WiFi
      • Restaurant
      • Fitness Center
      • Free Parking
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    • Truman Hotel
      Ranked #19 overall in Key West hotels
      9.02 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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    • Knowles House B&B
      Ranked #10 overall in Key West hotels
      10.03 reviews
      Popular withHipstersLGBTQ

      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 #11 overall in Key West hotels
      9.33 reviews
      Popular withBusinessLuxuryFamilies

      Very nice! They have airport shuttle. They have a shuttle to take you down to Duvall Street and pick you up. Nice restaurant. Great pool and its beach side.

      • Free WiFi
      • Restaurant
      • Swimming Pool
      • Fitness Center
      • Airport Transfer
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    • Captain Pip's Boat Rental & Jet Ski
      Ranked #3 overall in Marathon hotels
      9.33 reviews
      Popular withHipstersOutdoorsyAdventure

      Boat was great. People were good. Paperwork was a little intense and prices quoted to replace broken or missing items were more than double the cost in many instances. Also, ...

      • Free WiFi
      • Restaurant
      • Swimming Pool
      • Free Parking
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    • Hyatt Centric Key West Resort and Spa
      Ranked #12 overall in Key West hotels
      8.73 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
      ReviewsPhotosAmenitiesMaploadingclose
    • Hyatt Windward Pointe
      Ranked #15 overall in Key West hotels
      10.02 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 Gardens Hotel
      Ranked #43 overall in Key West hotels
      8.01 review
      Popular withGreenHistoryOutdoorsy

      Once upon a time, these grounds were the "Peggy Mills Botanical Garden," so strolling the property’s shady brick walkways is a pleasure. The main house dates back to 1870. There’s ...

      • Free WiFi
      • Restaurant
      • Free Breakfast
      • Pets Allowed
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    • Venture Out Resort
      Ranked #1 overall in Cudjoe Key hotels
      8.02 reviews
      Popular withFamiliesOutdoorsyAdventure

      We've stayed here 30 years. Absolutely awesome place to have your boat right behind your manufacturered home on the Atlantic Ocean.

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      • DoubleTree Resort by Hilton Grand Key - Key West
        Ranked #13 overall in Key West hotels
        6.85 reviews
        Popular withBusinessLuxuryFamilies

        Have stayed here several times over the years. Love the the free ride to Old Towne Key West so that you can enjoy all the "adult beverages" you desire without ...

        • Free WiFi
        • Restaurant
        • Swimming Pool
        • Fitness Center
        • Free Parking
        • Pets Allowed
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      • Dolphin Marina & Cottages
        Ranked #2 overall in Little Torch Key hotels
        8.04 reviews
        Popular withAdventureOutdoorsy
        • Free Parking
        • Pets Allowed
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      • Coral Hammock Key West by KeysCaribbean
        Ranked #24 overall in Key West hotels
        8.02 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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