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Anna Maria Vacations

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

Hotwire can help you find your travel bliss with Anna Maria 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 Anna Maria

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 Anna Maria 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 Anna Maria well.

Anna Maria Flight + Hotel packages

Top Hotel Deals

See all 184 Hotels in Anna Maria
Anna Maria Beach Cottages

Anna Maria Beach Cottages

112 Oak Ave, Anna Maria
    3.0 out of 5.0
     
     

    Situated near the beach, this cottage is within a 15-minute walk of Island Players and Anna Maria Island Museum and Historical Park. Historic Green Village and ...

    Sunrise Garden Resort

    Sunrise Garden Resort

    512 Spring Avenue, Anna Maria
      3.0 out of 5.0
       
       

      Situated near the beach, this condo building is steps from Historic Green Village and Anna Maria City Pier. Anna Maria Island Museum and Historical Park and ...

      604 N Shore Cottage #54637 1 Bedroom 1 Bathroom Cottage

      604 N Shore Cottage #54637 1 Bedroom 1 Bathroom Cottage

      604 North Shore, Anna Maria
        3.0 out of 5.0
         
         

        Situated in Anna Maria, this vacation home is close to Anna Maria Island Museum and Historical Park, Island Players, and Historic Green Village. Also nearby ...

        Sandy Toes

        Sandy Toes

        804 Gladiolus St, Anna Maria
          3.5 out of 5.0
           
           

          Situated in Anna Maria, this vacation home is within a 15-minute walk of Bean Point Beach and Anna Maria City Pier. Anna Maria Island Museum and Historical Park ...

          604 N Shore Cabin #54645 2 Bedrooms 1 Bathroom Cabin

          604 N Shore Cabin #54645 2 Bedrooms 1 Bathroom Cabin

          604 North Shore, Anna Maria
            3.5 out of 5.0
             
             

            Situated in Anna Maria, this vacation home is close to Anna Maria Island Museum and Historical Park, Island Players, and Historic Green Village. Also nearby ...

            Still Water Cottage #54630 1 Bedroom 1 Bathroom Cottage

            Still Water Cottage #54630 1 Bedroom 1 Bathroom Cottage

            604 North Shore Drive, Anna Maria
              3.0 out of 5.0
               
               

              Situated in Anna Maria, this vacation home is close to Anna Maria Island Museum and Historical Park, Island Players, and Historic Green Village. Also nearby ...

              Bikini Bottom by RedAwning

              Bikini Bottom by RedAwning

              213 Periwinkle Plaza, Anna Maria
                4.0 out of 5.0
                 
                 

                Situated in Anna Maria, this vacation home is within 1 mi (2 km) of Island Players, Anna Maria Island Museum and Historical Park, and Historic Green Village. ...

                LaRaya 801 Jacaranda by RedAwning

                LaRaya 801 Jacaranda by RedAwning

                801 Jacaranda Road, Anna Maria
                  4.0 out of 5.0
                   
                   

                  Situated near the beach, this vacation home is within a 15-minute walk of Bean Point Beach and Anna Maria City Pier. Anna Maria Island Museum and Historical ...

                  Conch Shell

                  Conch Shell

                  215 Elm Ave, Anna Maria
                    3.5 out of 5.0
                     
                     

                    Situated in Anna Maria, this vacation home is within a 5-minute walk of Island Players and Anna Maria Island Museum and Historical Park. Historic Green Village ...

                    Blue Dolphin Inn - Ibis by RedAwning

                    Blue Dolphin Inn - Ibis by RedAwning

                    780 Jacaranda Road, Anna Maria
                      3.0 out of 5.0
                       
                       

                      Situated in Anna Maria, this apartment building is close to Bean Point Beach, Anna Maria Island Museum and Historical Park, and Historic Green Village. Also ...

                      Top Flight Deals

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