Choose from AARP Discount Islamorada Hotels with Free Cancellation

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Estimated price for 1 night/2 adults

Islander Resort

Islander Resort

82100 Overseas Highway, Islamorada, FL
Islander Resort
  • Free Cancellation
  • Reserve now, pay when you stay
3.0 out of 5.0
 
 

Nestled on the beach, this Islamorada resort is 0.6 mi (1 km) from Florida Keys Brewing Co. and 2.7 mi (4.3 km) from Theater of the Sea. Hurricane Monument and ...

Islander ResortGet Rates

Postcard Inn Beach Resort & Marina

Postcard Inn Beach Resort & Marina

84001 Overseas Hwy, Islamorada, FL
Postcard Inn Beach Resort & Marina
    3.0 out of 5.0
     
     

    Nestled on the beach, this Islamorada resort is within 1 mi (2 km) of Windley Key Fossil Reef Geological State Park and Theater of the Sea. Founders Park and ...

    Postcard Inn Beach Resort & MarinaGet Rates

    Chesapeake Beach Resort

    Chesapeake Beach Resort

    83409 Overseas Hwy, Islamorada, FL
    Chesapeake Beach Resort
    • Free Cancellation
    • Reserve now, pay when you stay
    2.5 out of 5.0
     
     

    Nestled on the beach, this Islamorada resort is within 1 mi (2 km) of History of Diving Museum and Theater of the Sea. Windley Key Fossil Reef Geological State ...

    Chesapeake Beach ResortGet Rates

    Amara Cay Resort

    Amara Cay Resort

    80001 Overseas Hwy, Islamorada, FL
    Amara Cay Resort
      3.5 out of 5.0
       
       

      Nestled on the beach, this Islamorada hotel is within a 15-minute walk of Bud n' Mary's Dive Center and Indian Key Historic State Park. Hurricane Monument and ...

      Amara Cay ResortGet Rates

      La Siesta Resort & Marina

      La Siesta Resort & Marina

      80241 Overseas Highway, Islamorada, FL
      La Siesta Resort & Marina
        3.0 out of 5.0
         
         

        Located in Islamorada, this beachfront resort is in the historical district and within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive ...

        La Siesta Resort & MarinaGet Rates

        Sunset Inn

        Sunset Inn

        82200 Overseas Hwy, Islamorada, FL
        Sunset Inn
          3.0 out of 5.0
           
           

          Situated in Islamorada, this inn is 0.8 mi (1.3 km) from History of Diving Museum and 2.5 mi (4 km) from Theater of the Sea. Hurricane Monument and Florida Keys ...

          Sunset InnGet Rates

          Pelican Cove Resort & Marina

          Pelican Cove Resort & Marina

          84457 Overseas Highway, Islamorada, FL
          Pelican Cove Resort & Marina
            3.0 out of 5.0
             
             

            Nestled on the beach, this Islamorada hotel is within a 10-minute walk of Windley Key Fossil Reef Geological State Park and Theater of the Sea. History of Diving ...

            Pelican Cove Resort & MarinaGet Rates

            La Jolla Resort

            La Jolla Resort

            82216 Overseas Highway, Islamorada, FL
            La Jolla Resort
              2.5 out of 5.0
               
               

              Nestled on the beach, this Islamorada hotel is 0.7 mi (1.1 km) from History of Diving Museum and 2.4 mi (3.8 km) from Theater of the Sea. Florida Keys Brewing ...

              La Jolla ResortGet Rates

              Hadley House Islamorada

              Hadley House Islamorada

              82749 Overseas Hwy, Islamorada, FL
              Hadley House Islamorada
                3.5 out of 5.0
                 
                 

                Nestled on the beach, this Islamorada hotel is 0.4 mi (0.7 km) from History of Diving Museum and 2.1 mi (3.3 km) from Theater of the Sea. Florida Keys Brewing ...

                Hadley House IslamoradaGet Rates

                Cheeca Lodge & Spa

                Cheeca Lodge & Spa

                81801 Overseas Highway, Mile Marker 82, Marker 82, Islamorada, FL
                Cheeca Lodge & Spa
                  4.0 out of 5.0
                   
                   

                  Nestled on the beach, this Islamorada resort is 0.3 mi (0.5 km) from Florida Keys Brewing Co. and 2.9 mi (4.7 km) from Theater of the Sea. Hurricane Monument ...

                  Cheeca Lodge & SpaGet Rates

                  Drop Anchor

                  Drop Anchor

                  84959 Overseas Highway, 222, Islamorada, FL
                  Drop Anchor
                    3.0 out of 5.0
                     
                     

                    Situated in Islamorada, this hotel is within a 10-minute walk of Windley Key Fossil Reef Geological State Park and Theater of the Sea. Founders Park and History ...

                    Drop Anchor Get Rates

                    Fisher Inn Resort & Marina

                    Fisher Inn Resort & Marina

                    84951 Overseas Hwy, Islamorada, FL
                    Fisher Inn Resort & Marina
                      3.5 out of 5.0
                       
                       

                      Located in Islamorada, this beachfront motel is in the city center and within a 10-minute walk of Windley Key Fossil Reef Geological State Park and Theater of ...

                      Fisher Inn Resort & MarinaGet Rates

                      Pines & Palms Resort

                      Pines & Palms Resort

                      80401 Old Hwy, Islamorada, FL
                      Pines & Palms Resort
                        3.0 out of 5.0
                         
                         

                        Nestled on the beach, this Islamorada resort is within a 15-minute walk of Indian Key Historic State Park and Bud n' Mary's Dive Center. Hurricane Monument and ...

                        Pines & Palms ResortGet Rates

                        Sands of Islamorada

                        Sands of Islamorada

                        80051 Overseas Highway, Islamorada, FL
                        Sands of Islamorada
                          2.5 out of 5.0
                           
                           

                          Situated by the sea, this hotel is 0.3 mi (0.5 km) from Bud n' Mary's Dive Center and 3 mi (4.8 km) from History of Diving Museum. Theater of the Sea and Windley ...

                          Sands of IslamoradaGet Rates

                          The Caribbean Resort

                          The Caribbean Resort

                          117 Carroll St, Islamorada, FL
                          The Caribbean Resort
                            3.5 out of 5.0
                             
                             

                            This family-friendly Islamorada resort is located on the waterfront, within 2 mi (3 km) of Hurricane Monument and History of Diving Museum. Bud n' Mary's Dive ...

                            The Caribbean ResortGet Rates

                            The Islands of Islamorada

                            The Islands of Islamorada

                            82779 Old Hwy, Islamorada, FL
                            The Islands of Islamorada
                              4.0 out of 5.0
                               
                               

                              Nestled on the beach, this Islamorada villa is 0.3 mi (0.6 km) from History of Diving Museum and 2 mi (3.2 km) from Theater of the Sea. Florida Keys Brewing ...

                              The Islands of IslamoradaGet Rates

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                              Your Guide to Islamorada Hotels

                              If you're looking for a good rate for when you head to Islamorada, The AARP® Travel Center Powered by Expedia® has plenty of options available for you. The AARP Travel Center Best Price Guarantee ensures that you'll get the best rates available. Use your membership advantage to book a hotel that's closest to the sights you want to see, or even at a 5-star resort that offers the most luxurious amenities. With AARP Travel Center, your hotel reservation options will be endless.

                              Hotels Near Islamorada's Attractions

                              In Islamorada, we have lined up 1052 hotels that offer fantastic rates through the AARP Travel Center powered by Expedia. Once you get settled in your Islamorada hotel room, you can investigate all this region has to offer. You can ask your hotel's front desk or click on our "Things To Do" tab if you are unsure where start off your vacation in Islamorada. If golfing is your go-to activity on vacation, we can help you out. You are in luck, as Islamorada has 1 courses that you can work on your game at. Thanks to our discounts through AARP Travel Center, you'll be able to relax and enjoy your stay knowing you scored the hottest deals.

                              Reserve Your Islamorada Holiday Today

                              We will make it simple for you and your family to book your next hotel stay. It doesn't matter whether you are coming to Islamorada for business or to relax, we are going to make sure that you get the best prices around. Once you are willing to plan your golfer's getaway, we'll help you make all the arrangements. And you will not have to fret about breaking the bank to have a good time, thanks to our discounted vacations. With AARP, you'll look forward to planning your next vacation. You'll have peace of mind throughout your entire vacation. Why? You scored the best deal possible. Book with the Travel Center, and your wallet will be glad about your travels.