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

Islamorada Vacations

Pack those stellar shades. We have Islamorada vacation deals for you!

If there’s one thing you should spend in this busy world, it’s your vacation days. We know it’s easy to hang onto them, but Hotwire votes for putting them to use. It’s time to let an adventure lead you away from the daily grind. Stock up on what really matters on your trip to Islamorada – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Islamorada vacation packages. Bundling your hotel, car and flight means more unexpected fun with the money you saved. We’ll cover the bases; now it’s time for you to get up and go!

Pack everything you want – then take half of it out

We mean it. It’s far too easy to over-pack. We recommend picking your essentials and washing them along the way. Then you’ll have room for that goofy souvenir you know you want – or for some new outfits from that cute boutique you discover.

Bring comfortable walking shoes on your trip to Islamorada

No one should have to endure walking tours in dress shoes or high heels. No one.

Bring photocopies of your passport or license

You flew home from a great Islamorada vacation but your most important documents stayed behind. We’ve heard that story before and recommend keeping an extra copy on hand – just in case. Hey, at least it wasn’t a family member.

Don’t underestimate the power of earplugs

Among crying babies, rowdy crowds and honking horns, take our word for it. One pair can save you from the zombie-like state of a sleepless night.

Always carry some cash

You’ll be ready for anything from an evil ATM to lost credit cards. Holding a little extra cash in your wallet and carry-on means you can breathe easy if anything unexpected pops up.

Explore like a local

Guidebooks and maps are great for getting an overview of the place, but to really dig in, go where the locals go. Pick up a newspaper or city magazine to see what restaurants and neighborhoods are hot. Check events listings and go see a band or attend a street festival. Or ask your friends for recommendations. You’d be surprised who in your circle knows Islamorada well.

Islamorada Flight + Hotel packages

Top Hotel Deals

See all 207 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$182

    Amara Cay Resort$182
    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$195

        Pelican Cove Resort & Marina$195
        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
              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
                    Pines & Palms Resort

                    Pines & Palms Resort

                    80401 Old Hwy, Islamorada
                      3.0 out of 5.0
                       
                       

                      Nestled on the beach, this Islamorada resort is within 1 mi (2 km) of Bud n' Mary's Dive Center and Hurricane Monument. History of Diving Museum is 2.7 mi (4.3 ...

                      Pines & Palms Resort$199

                      Pines & Palms Resort$199

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.