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Siesta Key Vacations

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

Hotwire can help you find your travel bliss with Siesta 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 Siesta 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 Siesta 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 Siesta Key well.

Siesta Key Flight + Hotel packages

Top Hotel Deals

See all 423 Hotels in Siesta Key
Tropical Beach Resorts

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key
    3.5 out of 5.0
     
     

    Tropical Beach Resorts is located on Florida's Siesta Key barrier island. Just across the road is Crescent Village with its restaurants and shops, while hiking, ...

    Tropical Beach Resorts$150

    Tropical Beach Resorts$150
    Siesta Key Beachside Villas

    Siesta Key Beachside Villas

    124 Columbus Blvd, Siesta Key
      4.0 out of 5.0
       
       

      This villa is located in Siesta Key (Siesta Key Village), close to the beach, Siesta Key Public Beach, St. Armands Circle, and South Lido Park. Local attractions ...

      Turtle Beach Resort and Inn

      Turtle Beach Resort and Inn

      9049 Midnight Pass Road, Siesta Key
        3.5 out of 5.0
         
         

        Situated by the ocean, this romantic resort is within a 10-minute walk of Turtle Beach and Jim Neville Marine Preserve. Point of Rocks and Siesta Key Marina ...

        Captiva Beach Resort

        Captiva Beach Resort

        6772 Sara Sea Circle, Siesta Key
          2.0 out of 5.0
           
           

          Nestled on the beach, this Siesta Key condo building is 0.5 mi (0.8 km) from Siesta Key Marina and 2 mi (3.2 km) from Siesta Key Public Beach. Crescent Beach ...

          Captiva Beach Resort$127

          Captiva Beach Resort$127
          Minorga On The Key Village Condos

          Minorga On The Key Village Condos

          5108-5144 Calle Minorga, Siesta Key
            3.5 out of 5.0
             
             

            Located in Siesta Key Village, this condo building is within 3 mi (5 km) of Siesta Key Public Beach, Crescent Beach, and Siesta Key Marina. Marie Selby Botanical ...

            Minorga On The Key Village Condos$149

            Minorga On The Key Village Condos$149
            Beach Club at Siesta Key by RVA

            Beach Club at Siesta Key by RVA

            6732 Sarasea Circle, Siesta Key
              3.5 out of 5.0
               
               

              Situated by the ocean, this condo building is 0.5 mi (0.7 km) from Siesta Key Marina and 2 mi (3.2 km) from Siesta Key Public Beach. Point of Rocks and Crescent ...

              Tropical Breeze Resort

              Tropical Breeze Resort

              140 Columbus Blvd., Siesta Key
                3.0 out of 5.0
                 
                 

                Offering direct access to the beach, this Siesta Key Village condo building is in the entertainment district and within 3 mi (5 km) of Siesta Key Public Beach, ...

                Tropical Breeze Resort$167

                Tropical Breeze Resort$167
                Sea Club II Cottages by Beachside Mgt

                Sea Club II Cottages by Beachside Mgt

                5955 Midnight Pass Road, Siesta Key
                  3.0 out of 5.0
                   
                   
                  Bianco Sands by Beachside Management

                  Bianco Sands by Beachside Management

                  1126 Point of Rocks Road, Siesta Key
                    3.5 out of 5.0
                     
                     

                    Situated near the beach in Siesta Key, this condo resort is close to Point of Rocks, Crescent Beach and Siesta Key Marina. Local attractions also include Siesta ...

                    Casa del Miramar by Beachside Management

                    Casa del Miramar by Beachside Management

                    94 Columbus Blvd, Siesta Key
                       
                       

                      This condo building is located in Siesta Key (Siesta Key Village), close to the beach, Siesta Key Public Beach, St. Armands Circle, and South Lido Park. Local ...

                      Top Flight Deals

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