Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Islamorada Flight + Hotel packages

Top Islamorada Hotels Deals

See all 390 Hotels in Islamorada
Amara Cay Resort

Amara Cay Resort

80001 Overseas Hwy, Islamorada
    3.5 out of 5.0
     
     

    Nestled on the beach, this Islamorada hotel is within 3 mi (5 km) of Bud n' Mary's Dive Center, Lignumvitae Key Botanical State Park, and Hurricane Monument. ...

    Amara Cay Resort$179

    Amara Cay Resort$179
    Creekside Inn Islamorada

    Creekside Inn Islamorada

    90611 Old Highway, Islamorada
      2.5 out of 5.0
       
       

      Located in the heart of Islamorada, this motel is 3.1 mi (5 km) from Florida Keys Wild Bird Rehabilitation Center and within 6 mi (10 km) of Harry Harris Park ...

      Creekside Inn Islamorada$104

      Creekside Inn Islamorada$104
      Pelican Cove Resort & Marina

      Pelican Cove Resort & Marina

      84457 Overseas Highway, Islamorada
        3.0 out of 5.0
         
         

        Nestled on the beach, this Islamorada hotel is within a 15-minute walk of Theater of the Sea and Windley Key Fossil Reef Geological State Park. History of Diving ...

        Pelican Cove Resort & Marina$179

        Pelican Cove Resort & Marina$179
        Drop Anchor Resort and Marina

        Drop Anchor Resort and Marina

        84959 Overseas Highway, 222, Islamorada
          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 Resort and Marina$135

          Drop Anchor Resort and Marina$135
          Chesapeake Beach Resort

          Chesapeake Beach Resort

          83409 Overseas Hwy, Islamorada
            2.5 out of 5.0
             
             

            Renowned for its fishing, Islamorada is part of the Florida Keys - and Chesapeake Beach Resort puts guests steps from its sun-kissed shoreline. Those who can ...

            Chesapeake Beach Resort$143

            Chesapeake Beach Resort$143
            La Siesta Resort & Marina

            La Siesta Resort & Marina

            80241 Overseas Highway, Islamorada
              3.0 out of 5.0
               
               

              This all suites resort with 1 marina and 6-acres of ocean front is the premier destination for a family vacation in the Florida Keys. We are located in the Sport ...

              La Siesta Resort & Marina$194

              La Siesta Resort & Marina$194
              Lime Tree Bay Resort

              Lime Tree Bay Resort

              68500 Overseas Hwy, Long Key
                3.5 out of 5.0
                 
                 

                This waterfront resort sits on 1/4 mile of tropical waterfront in the heart of the Florida Keys. Close to Long Key State Park and Dolphin Research Center.

                Lime Tree Bay Resort$107

                Lime Tree Bay Resort$107
                Postcard Inn Beach Resort & Marina

                Postcard Inn Beach Resort & Marina

                84001 Overseas Hwy, Islamorada
                  3.0 out of 5.0
                   
                   

                  Postcard Inn Beach Resort & Marina sits directly on a private beach in Islamorada, a 30-minute drive from Key Largo. Guests can walk 5 minutes to Theater of ...

                  Postcard Inn Beach Resort & Marina$223

                  Postcard Inn Beach Resort & Marina$223
                  The Moorings Village

                  The Moorings Village

                  123 Beach Rd, Islamorada
                    3.5 out of 5.0
                     
                     

                    Located in Islamorada, this beachfront villa is in the entertainment district and within 3 mi (5 km) of Hurricane Monument, History of Diving Museum, and Bud ...

                    Cheeca Lodge & Spa

                    Cheeca Lodge & Spa

                    81801 Overseas Highway, Mile Marker 82, Islamorada
                      4.0 out of 5.0
                       
                       

                      Located on Upper Matecumbe Key, Islamorada, Cheeca Lodge & Spa is less than a mile from the Hurricane Monument. It's a 2-minute drive to the History of Diving ...

                      Cheeca Lodge & Spa$220

                      Cheeca Lodge & Spa$220