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Featured Florida Keys Hotels with a Pool

See all 848 Properties in Florida Keys
Southernmost Beach Resort

Southernmost Beach Resort

1319 Duval Street, Key West
  • Free Cancellation
  • Reserve now, pay when you stay
4.0 out of 5.0
 
 
4.5 out of 5 (3,472 reviews)
Not the last time I hopeThis was our first time staying at the Dewey's house, B&B in general for the first time as well. Excellent room and staff! Will recommend over waldord or any other big resorts! Such an awesome hotel and LT was so great when she greeted us at the door when we first came in. We loved the breakfast ...
Jun 21, 2018

Southernmost Beach Resort$229

Southernmost Beach Resort$229
24 North Hotel Key West

24 North Hotel Key West

3820 North Roosevelt Boulevard, Key West
  • Free Cancellation
  • Reserve now, pay when you stay
4.0 out of 5.0
 
 
4.1 out of 5 (1,241 reviews)
Fair. O.K.Rust running down the shower towel rack can be easily fixed, but is not. Room not as clean as it should be. 3 great hotel staff members at desk. Young man not helpful. Pool area good and outside bar very nice. 1/2 price drinks appreciated (made real price reasonable). Just charge 1/2 prince to drink ...
Jun 4, 2018

24 North Hotel Key West$152

24 North Hotel Key West$152
Best Western Key Ambassador Resort Inn

Best Western Key Ambassador Resort Inn

3755 S Roosevelt Blvd, Key West
  • Free Cancellation
  • Reserve now, pay when you stay
2.5 out of 5.0
 
 
4.0 out of 5 (1,733 reviews)
As expected The resort was clean and most of staff friendly. The downfall is the cheeckie hut staff was bad. Twice I was ignored by the bartender. And it was not busy. There was only two other people there at the time. Watching the TV was more important.
Jun 9, 2018
The Gates Hotel Key West

The Gates Hotel Key West

3824 N Roosevelt Blvd, Key West
  • Free Cancellation
  • Reserve now, pay when you stay
4.0 out of 5.0
 
 
4.3 out of 5 (1,257 reviews)
Awesome hotel Free shuttle was awesome but still only a 5-10 min drive if we chose to drive into town ourselves. Room was clean, well decorated, and comfortable. It did have a little bit of a musty smell when we initially walked in but most likely from the humidity. Check in and check out was smooth. Pool and ...
Jun 19, 2018

The Gates Hotel Key West$161

The Gates Hotel Key West$161
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
    3.5 out of 5.0
     
     
    4.3 out of 5 (1,332 reviews)
    As much fishing in 5 days as possibleDefinitely give this place 5 stars! Great location, the cleanest rooms. Great drinks at bar . Great food . Fantastic customer service. Ever time you see the g m on the property he speaks to you , along with 95%of the employees . Well worth it ! Marc c
    Jun 20, 2018

    Amara Cay Resort$199

    Amara Cay Resort$199
    Parrot Key Hotel & Resort

    Parrot Key Hotel & Resort

    2801 N Roosevelt Blvd, Key West
      4.0 out of 5.0
       
       
      4.2 out of 5 (2,191 reviews)
      Nice hotel. Close to the water. Nice staff.Pro: Room is large and comfortable. Location is convenient. Staff are nice. It also has complementary shuttle service to downtown if you need transportation. Con: This property seems to be relatively old and is NOT sound-proof. If you're a light sleeper, or you really care about noise level - or ...
      Sep 14, 2017
      Silver Palms Inn

      Silver Palms Inn

      830 Truman Ave, Key West
      • Free Cancellation
      • Reserve now, pay when you stay
      3.5 out of 5.0
       
       
      4.5 out of 5 (1,867 reviews)
      Lovely renovated hotel with great proximityWe loved this hotel. It is newly renovated with spacious, spotless rooms. It is a bit off Duval Street, but that worked perfect for us since we have young children. Would stay again in a heartbeat.
      Jun 16, 2018

      Silver Palms Inn$159

      Silver Palms Inn$159
      Sheraton Suites Key West

      Sheraton Suites Key West

      2001 S Roosevelt Blvd, Key West
      • Free Cancellation
      • Reserve now, pay when you stay
      3.5 out of 5.0
       
       
      4.2 out of 5 (2,092 reviews)
      Close to the beachThe room was very clean and a great size for my family of 5. Staff was friendly and helpful. We arrived at the hotel 5 hours before check-in and the staff was able to hold our luggage and we took their free shuttle to downtown to eat until we got the call that our room was ready. The shuttle ran ...
      Jun 21, 2018

      Sheraton Suites Key West$188

      Sheraton Suites Key West$188
      Fairfield Inn and Suites by Marriott Key West

      Fairfield Inn and Suites by Marriott Key West

      2400 N Roosevelt Blvd, Key West
      • Free Cancellation
      • Reserve now, pay when you stay
      3.5 out of 5.0
       
       
      4.1 out of 5 (1,512 reviews)
      Excellent StaffHad a great time! Hotel is clean and excellent staff. Room also clean, but facing parking lot.
      Jun 21, 2018
      Islander Resort

      Islander Resort

      82100 Overseas Highway, Islamorada
        3.0 out of 5.0
         
         
        4.2 out of 5 (1,745 reviews)
        Our favorite hotel in the keys!Classic keys motel...feels like we are transported back to the 1950s when we are on property...with a modern twist and Guy Harvey artwork abound. Lots of time in the pool (with drinks served poolside) or cooking out on the backyard grills with the kids. You are only a few steps from the ocean with ...
        Sep 13, 2017

        Islander Resort$221

        Islander Resort$221
        Hyatt Place Marathon Florida Keys

        Hyatt Place Marathon Florida Keys

        1996 Overseas Highway, Marathon
        • Free Cancellation
        • Reserve now, pay when you stay
        3.0 out of 5.0
         
         
        4.5 out of 5 (1,481 reviews)
        Great Hotel in MarathonHyatt Place is a very clean and modern place to relax or conduct business. It is located on the Faro Blanco Marina and light house. The hotel staff is very pleasant and personable. They greet you and have a wonderful smile. We had no issues with our booking despite having to pay in advance. The buffet ...
        Jun 10, 2018

        Hyatt Place Marathon Florida Keys$179

        Hyatt Place Marathon Florida Keys$179
        The Southernmost Inn-Adults Only

        The Southernmost Inn-Adults Only

        525 United Street, Key West
        • Free Cancellation
        • Reserve now, pay when you stay
        2.5 out of 5.0
         
         
        4.1 out of 5 (996 reviews)
        Love Southernmost InnGreat staff, comfy rooms. Toilet backed up, parking sucks.
        Jun 22, 2018

        The Southernmost Inn-Adults Only$149

        The Southernmost Inn-Adults Only$149
        Oceans Edge Key West Resort, Hotel & Marina

        Oceans Edge Key West Resort, Hotel & Marina

        5950 Peninsular Avenue, Key West
        • Free Cancellation
        • Reserve now, pay when you stay
        4.0 out of 5.0
         
         
        4.5 out of 5 (570 reviews)
        Beautiful HotelThe hotel facade and hampton's style decorating is perfection, the grounds and facilities excellent. The location of the building that we stayed in was poor and far away from everything, try and avoid Building 4 if you can, access to everything from here is not thought through. The hotel reception ...
        Jun 13, 2018
        Fairfield Inn & Suites by Marriott Key West, Keys Collection

        Fairfield Inn & Suites by Marriott Key West, Keys Collection

        3852 North Roosevelt Boulevard, Key West
        • Free Cancellation
        • Reserve now, pay when you stay
        3.0 out of 5.0
         
         
        4.1 out of 5 (1,036 reviews)
        Loving Key West We will be back...loved the Dry Tortuga, the excellent fishing and superb food
        Jun 16, 2018

        Fairfield Inn & Suites by Marriott Key West, Keys Collection$149

        Fairfield Inn & Suites by Marriott Key West, Keys Collection$149
        Lime Tree Bay Resort

        Lime Tree Bay Resort

        68500 Overseas Hwy, Long Key
          3.5 out of 5.0
           
           
          4.2 out of 5 (701 reviews)
          Beautiful views with a great amenitiesThe bed was uncomfortable but aside from that this was the perfect place to stay. Close to so many cool places and offers so many things on site with no charge.
          Jun 11, 2018

          Lime Tree Bay Resort$119

          Lime Tree Bay Resort$119
          Hawks Cay Resort

          Hawks Cay Resort

          61 Hawks Cay Blvd, Duck Key
            4.0 out of 5.0
             
             
            4.2 out of 5 (1,930 reviews)
            Nice resort with its own beach and 2 pools We love staying at Hawk's Cay. I love that they have heir own little private beach/lagoon area. Main pool is beautiful, but when you want to get away from other people's kids, there is an adult pool as well. It's a little older but still really nice. My only complaint is that is that the menus have ...
            Sep 17, 2017
            DoubleTree Resort by Hilton Grand Key - Key West

            DoubleTree Resort by Hilton Grand Key - Key West

            3990 S Roosevelt Blvd, Key West
            • Free Cancellation
            • Reserve now, pay when you stay
            3.5 out of 5.0
             
             
            4.2 out of 5 (2,053 reviews)
            Key West can be trickyKey West hotel options are many and few a great. I’m a platinum SPG which gets me into all Starwood properties(Westin, Sheraton and others) all Marriott properties and Ritz (no Ritz in Key West) so I have options. Accustomed to great accomadations, none of the properties matched to the Double Tree ...
            May 10, 2018
            Marina Del Mar Resort and Marina

            Marina Del Mar Resort and Marina

            527 Caribbean Drive, Key Largo
            • Free Cancellation
            • Reserve now, pay when you stay
            2.5 out of 5.0
             
             
            3.6 out of 5 (1,900 reviews)
            nice hotel close to the beachRooms were very nice and clean, staff was friendly and very customer service oriented, was impressed with how dog friendly the hotel was that was my main concern. Will plan again to stay there with my family.
            Jun 23, 2018

            Marina Del Mar Resort and Marina$109

            Marina Del Mar Resort and Marina$109
            Holiday Inn Key Largo

            Holiday Inn Key Largo

            99701 Overseas Hwy, Key Largo
            • Free Cancellation
            • Reserve now, pay when you stay
            3.0 out of 5.0
             
             
            3.9 out of 5 (1,260 reviews)
            ComfyClean, quiet, simple! Several stores within walking distance of hotel. CVS, Walgreens and Starbucks.
            May 29, 2018

            Holiday Inn Key Largo$129

            Holiday Inn Key Largo$129
            Map

            Pocket Guide: Hotels with a Pool in Florida Keys

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