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Longboat Key Vacations

Pack those stellar shades. We have Longboat Key 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 Longboat Key – great memories and a tall tale or two.

Hotwire can help you find your travel bliss with Longboat Key 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 Longboat Key

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 Longboat Key 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 Longboat Key well.

Longboat Key Flight + Hotel packages

Top Hotel Deals

See all 129 Hotels in Longboat Key
Zota Beach Resort

Zota Beach Resort

4711 Gulf of Mexico Dr, Longboat Key
    3.5 out of 5.0
     
     

    This Longboat Key resort is on the beach, 2 mi (3.2 km) from Cannons Marina, and within 6 mi (10 km) of Beer Can Island and Coquina Beach. Brandenton Beach and ...

    The Beach on Longboat Key by RVA

    The Beach on Longboat Key by RVA

    3465 Gulf of Mexico Drive, Longboat Key
      3.0 out of 5.0
       
       

      Nestled on the beach, this Longboat Key condo building is within 6 mi (10 km) of Cannons Marina, Beer Can Island, and Mote Marine Aquarium. Marie Selby Botanical ...

      The Beach on Longboat Key by RVA$170

      The Beach on Longboat Key by RVA$170
      The Resort at Longboat Key Club

      The Resort at Longboat Key Club

      220 Sands Point Road, Longboat Key
        4.0 out of 5.0
         
         

        Nestled on the beach, this Longboat Key resort is 0.7 mi (1.1 km) from Mote Marine Aquarium and 1.6 mi (2.6 km) from St. Armands Circle. South Lido Park is 2.6 ...

        Beach Castle Resort by RVA

        Beach Castle Resort by RVA

        5310 Gulf of Mexico Dr, Longboat Key
          3.0 out of 5.0
           
           

          Nestled on the beach, this Longboat Key condo resort is 1.1 mi (1.8 km) from Cannons Marina and 3.1 mi (4.9 km) from Beer Can Island. Cortez Beach and Coquina ...

          Silver Sands Gulf Beach Resort by RVA

          Silver Sands Gulf Beach Resort by RVA

          5841 Gulf of Mexico Drive, Longboat Key
            3.0 out of 5.0
             
             

            Offering direct access to the beach, this Longboat Key condo building is within 3 mi (5 km) of Cannons Marina, Beer Can Island, and Cortez Beach. Coquina Beach ...

            Sea Club I Beach Resort

            Sea Club I Beach Resort

            4141 Gulf of Mexico Drive, Longboat Key
              3.0 out of 5.0
               
               

              This Longboat Key aparthotel is on the beach, 2.8 mi (4.4 km) from Cannons Marina, and within 6 mi (10 km) of Beer Can Island and Coquina Beach. Cortez Beach ...

              Casa Del Mar Longboat Key

              Casa Del Mar Longboat Key

              4621 Gulf of Mexico Dr, Longboat Key
                3.5 out of 5.0
                 
                 

                This Longboat Key condo resort is on the beach, 6.6 mi (10.6 km) from Mote Marine Aquarium, and within 16 mi (25 km) of St. Armands Circle and John and Mable ...

                Outrigger Resort by RVA

                Outrigger Resort by RVA

                5155 Gulf of Mexico Dr, Longboat Key
                  3.0 out of 5.0
                   
                   

                  This Longboat Key condo resort is on the beach, 1.3 mi (2.1 km) from Cannons Marina, and within 6 mi (10 km) of Beer Can Island and Coquina Beach. Cortez Beach ...

                  Cabana Beach Club by RVA

                  Cabana Beach Club by RVA

                  5851 Gulf of Mexico Drive, Longboat Key
                    2.0 out of 5.0
                     
                     

                    Nestled on the beach, this Longboat Key condo building is within 3 mi (5 km) of Cannons Marina, Beer Can Island, and Cortez Beach. Coquina Beach and Coquina ...

                    Bayou Hammock Pool Cottage by Wagner Realty

                    Bayou Hammock Pool Cottage by Wagner Realty

                    6533 Bayou Hammock, Longboat Key
                      3.0 out of 5.0
                       
                       

                      Situated in Longboat Key, this condo building is within 2 mi (3 km) of Beer Can Island, Coquina Baywalk, and Cortez Beach. Coquina Beach and Cannons Marina are ...

                      Top Flight Deals

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