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Top Florida Keys Hotels with Pools

The Southernmost Inn-Adults Only $125
The Southernmost Inn-Adults Only

The Southernmost Inn-Adults Only

525 United Street, Key West, FL
     
    4.6
    of 5, from 100 reviews
    2.5 out of 5.0 Stars

    2 outdoor pools, a spa tub, and a fitness center are all featured at this Victorian hotel. Relax with a drink at the poolside bar and enjoy the free continental breakfast each morning. A bar/lounge, a coffee shop, and a terrace are also provided.

    Oceans Edge Key West Resort, Hotel & Marina $118
    Oceans Edge Key West Resort, Hotel & Marina

    Oceans Edge Key West Resort, Hotel & Marina

    5950 Peninsular Avenue, Key West, FL
       
      4.5
      of 5, from 35 reviews
      4.0 out of 5.0 Stars

      A marina, 6 outdoor pools, and a 24-hour fitness center are all featured at this smoke-free hotel. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and perks like a free area shuttle.

      Amara Cay Resort $155
      Amara Cay Resort

      Amara Cay Resort

      80001 Overseas Hwy, Islamorada, FL
         
        4.4
        of 5, from 29 reviews
        3.5 out of 5.0 Stars

        A private beach, 2 restaurants, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and an area shuttle.

        Islander Resort $199
        Islander Resort

        Islander Resort

        82100 Overseas Highway, Islamorada, FL
           
          4.3
          of 5, from 23 reviews
          3.0 out of 5.0 Stars

          This resort features a private beach, 3 outdoor pools, and a restaurant. Traveling on business? Take advantage of the 2 conference rooms, as well as free WiFi in public areas and free Internet in public areas. Relax with a drink at one of the 2 poolside bars and enjoy perks like free self parking.

          Best Western Key Ambassador Resort Inn $149
          Best Western Key Ambassador Resort Inn

          Best Western Key Ambassador Resort Inn

          3755 S Roosevelt Blvd, Key West, FL
             
            4.3
            of 5, from 29 reviews
            2.5 out of 5.0 Stars

            This resort features a restaurant, an outdoor pool, and a poolside bar. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Relax with a drink at the bar/lounge and enjoy free perks like continental breakfast and free self parking.

            Southernmost Beach Resort $223
            Southernmost Beach Resort

            Southernmost Beach Resort

            1319 Duval Street, Key West, FL
               
              4.3
              of 5, from 118 reviews
              4.0 out of 5.0 Stars

              This romantic hotel features a full-service spa, 3 outdoor pools, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Traveling for business? Take advantage of the 24-hour business center, laundry service, and conference space.

              The Gates Hotel Key West $127
              The Gates Hotel Key West

              The Gates Hotel Key West

              3824 N Roosevelt Blvd, Key West, FL
                 
                4.3
                of 5, from 29 reviews
                4.0 out of 5.0 Stars

                This hotel features an outdoor pool, a fitness center, and a restaurant. Relax with a drink at the poolside bar and enjoy perks like free self parking and free WiFi. There's a bar/lounge on site, and laundry facilities and concierge services are also provided.

                Sheraton Suites Key West $207
                Sheraton Suites Key West

                Sheraton Suites Key West

                2001 S Roosevelt Blvd, Key West, FL
                   
                  4.2
                  of 5, from 111 reviews
                  3.5 out of 5.0 Stars

                  This resort features a restaurant, an outdoor pool, and a poolside bar. Traveling on business? Take advantage of the 2 conference rooms, 24-hour business center, and free airport shuttle. Enjoy the 24-hour fitness center and perks like free self parking and a free area shuttle.

                  24 North Hotel Key West $127
                  24 North Hotel Key West

                  24 North Hotel Key West

                  3820 North Roosevelt Boulevard, Key West, FL
                     
                    4.2
                    of 5, from 40 reviews
                    4.0 out of 5.0 Stars

                    This smoke-free hotel includes 3 restaurants, an outdoor pool, and a fitness center. Business travelers can take advantage of the free WiFi in public areas. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.

                    Parrot Key Hotel & Villas $169
                    Parrot Key Hotel & Villas

                    Parrot Key Hotel & Villas

                    2801 N Roosevelt Blvd, Key West, FL
                       
                      4.1
                      of 5, from 39 reviews
                      4.0 out of 5.0 Stars

                      This smoke-free resort features 4 outdoor pools, a fitness center, and a restaurant. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Unwind with a drink at the poolside bar and enjoy perks like a free area shuttle.

                      Silver Palms Inn $139
                      Silver Palms Inn

                      Silver Palms Inn

                      830 Truman Ave, Key West, FL
                         
                        4.1
                        of 5, from 24 reviews
                        3.5 out of 5.0 Stars

                        This hotel features a poolside bar, a bar/lounge, and an outdoor pool. Business travelers can take advantage of the free WiFi in public areas. Guests will appreciate freebies like continental breakfast and free self parking.

                        Fairfield Inn and Suites by Marriott Key West $143
                        Fairfield Inn and Suites by Marriott Key West

                        Fairfield Inn and Suites by Marriott Key West

                        2400 N Roosevelt Blvd, Key West, FL
                           
                          3.7
                          of 5, from 43 reviews
                          3.0 out of 5.0 Stars

                          This hotel features a restaurant, an outdoor pool, and a poolside bar. Enjoy the 24-hour fitness center and free perks like buffet breakfast and free self parking. There's a bar/lounge on site, and a 24-hour front desk and laundry facilities are also provided.

                          Travelers Like You Recently Booked These Florida Keys Hotels

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                          Hotels with a Pool in Florida Keys

                          Whether you’re traveling for vacation or business, nothing says “relaxation” quite like floating on an inflatable raft. For water-lovers like you, finding a hotel with a pool in Florida Keys is a must-do on the itinerary. From cannonballs to gentle wading, Travelocity will help you snag the perfect hotel so you can cool off however you need to.

                          Booking hotels in Florida Keys with a pool doesn’t mean you have to sacrifice your room amenities, either. You’ll still receive the same tender loving care from the friendly staff, fresh towels to dry off with, and tasty room service at your beck and call.

                          Florida Keys hotels with a pool are perfect for everyone from a solo traveler looking to get some exercise first thing in the morning to a big family who needs to keep the kiddos entertained. Many of these accommodations also offer a hot tub, so you can soak away any stress in the warm bubbles.

                          If you’re worried about prices, Travelocity won’t leave your wallet hanging out to dry. Book your hotel with us and rely on the Travelocity Price Guarantee to get the most affordable rates. You’ll soon be splashing around and exploring a new city, all from the home base of an affordable hotel.

                          Recent Florida Keys Hotel Reviews By Fellow Wanderers

                          *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.