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Tips for planning your Florida Keys holiday

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Holidays To Florida Keys

The Florida Keys are a strip of islands at the southernmost point of Florida. 

Once you pay a visit to this—the only living reef in the continental U.S.--you'll enjoy its endless blue waters, postcard-perfect sunsets and wild habitats. A Florida Keys holiday might include stops in Key Largo, the island village of Islamorada, Big Pine Key, Sugarloaf, and the iconic Key West. But these popular spots are just the tip of the proverbial reef as the Keys is a land of many adventures—and some paths are more travelled than others.

Things to do

Kick off your Florida Keys holidays in mainland Florida. If you land at Orlando International Airport, snag one of our Orlando car hire deals and start cruising in style. You'll cruise down the Overseas Highway, a 182-kilometre bridge that crosses islets of coral and limestone. Exit for attractions along the way: Explore the boardwalk in Key Largo, visit the Theatre of the Sea in Islamorada, and feed the deer in Big Pine Key (these tiny antlered creatures are exclusive to the Keys). You might hike the trails in Sugarloaf or Marathon and take a picnic for the beach. If you proceed to Key West, take a tour of the Ernest Hemingway House and the neighbouring Audubon House to learn some island history.

Shopping, dining & nightlife

"It's five o'clock somewhere" is a mantra throughout the Keys. Restaurants are open all hours to serve local seafood (conch chowder is a favourite) and a multitude of ethnic fare. Cuban, Caribbean, Thai and Japanese eateries are popular spots for tourists and locals alike. You'll also find plenty of American pubs that offer up the infamous "cheeseburger in paradise," in tribute to the endearing Jimmy Buffet song (he's a frequent visitor to Key West).

Florida Keys holiday packages provide heaps of places to shop at, so keep that credit card ready. Stop in Key Largo or Sugarloaf to pick out some flip-flops or a new bathing suit and stock up on seashells. Commerce is liveliest close to mainland and in the lower Keys; you'll find major retailers in these areas alongside independent small businesses that sell clothing, botanicals and other goods. If you love art, visit the local galleries. Find a print you just have to have? They’ll pack and ship your masterpieces back home to you.

Florida Keys packages aren’t complete without time spent on the water. Check out local evening escapes like schooner rides, wine tastings, and party cruises where you can sing and celebrate on the water. For late-night thrills, visit Key West where the Duvall Street party never ends—note that some of the bars are clothing-optional. In others, you can dance on the tables and raise a toast when the roosters crow (which is often, as many chickens live in the streets).

What's next?

Whether you’re ready to snag one of our Florida Keys deals or just want to spoil your family with Orlando holiday packages, Wotif has your back. Book your getaway today and head for sunny Florida tomorrow!


Guide to Exploring Florida Keys

Family Hotels in Florida Keys

Hawks Cay Resort

Hawks Cay Resort

61 Hawks Cay Blvd, Marathon, FL
    4.0 out of 5.0
     
     

    This Marathon resort is on the beach, 5.9 mi (9.5 km) from Curry Hammock State Park, and within 12 mi (20 km) of Long Key State Park and Conch Air (Bi Plane ...

    from AU$291

    Southernmost Beach Resort

    Southernmost Beach Resort

    1319 Duval Street, Key West, FL
      4.0 out of 5.0
       
       

      Located in Key West Historic District, this beachfront hotel is in the city centre and within 1 mi (2 km) of South Beach, Fort Zachary Taylor Historic State ...

      from AU$344

      Islander Resort

      Islander Resort

      82100 Overseas Highway, Islamorada, FL
        3.0 out of 5.0
         
         

        Nestled on the beach, this Islamorada resort is 0.7 mi (1.1 km) from Hurricane Monument and 2.7 mi (4.3 km) from Theater of the Sea. Bud n' Mary's Dive Center ...

        from AU$285

        Hyatt Place Marathon Florida Keys

        Hyatt Place Marathon Florida Keys

        1996 Overseas Highway, Marathon, FL
          3.0 out of 5.0
           
           

          Located in the heart of Marathon, this hotel is within 1 mi (2 km) of The Turtle Hospital and Pigeon Key Foundation. Seven Mile Bridge and Crane Point Museum ...

          from AU$220

          Romantic Hotels in Florida Keys

          Southernmost Beach Resort

          Southernmost Beach Resort

          1319 Duval Street, Key West, FL
            4.0 out of 5.0
             
             

            Located in Key West Historic District, this beachfront hotel is in the city centre and within 1 mi (2 km) of South Beach, Fort Zachary Taylor Historic State ...

            from AU$344

            Parrot Key Hotel & Villas

            Parrot Key Hotel & Villas

            2801 N Roosevelt Blvd, Key West, FL
              4.0 out of 5.0
               
               

              Situated on the waterfront, this romantic resort is within 3 miles (5 km) of Key West Naval Station, Smathers Beach and South Beach. Duval Street and Ernest ...

              from AU$277

              Pier House Resort & Spa

              Pier House Resort & Spa

              1 Duval St, Key West, FL
                4.0 out of 5.0
                 
                 

                Located in Key West Historic District, this beachfront resort is in the city centre, just steps away from Ripley's Believe It or Not, Key West Shipwreck Museum ...

                from AU$473

                Cheeca Lodge & Spa

                Cheeca Lodge & Spa

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

                  Nestled on the beach, this Islamorada resort is 0.4 mi (0.7 km) from Hurricane Monument and 2.9 mi (4.7 km) from Theater of the Sea. Bud n' Mary's Dive Center ...

                  from AU$279

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