Vacation Rentals & Beach Rentals in Anna Maria

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

3,069 beach rentals

(38) Excellent 

    123

    Ocean View 3 bedroom, pool, North Shore Drive

    Anna Maria Island / Anna Maria

    Anna Maria house

    3 6 min stay varies

    • 3 bedrooms
    • sleeps 6
    • min stay varies
    • Beach / lakeside relaxation
    • Nearest beach 0 mi
    • Swimming pool
    “Amazing Oceanview Pool Home and Perfect Location On Anna Maria Island” Let me first say that Mark (the home owner) exceeded any and all expectations for our 15th wedding Anniversary! We booked last minute and when we wanted to stay an additional day M
    …see more

    Price per night from

    $237

    Responds fast!
    avg. 49 minutes

    Price per night from

    $237

      0

      Charming cottage w/ free WiFi just two blocks from the beach, near free trolley!

      Anna Maria Island / Anna Maria

      Anna Maria house

      3 8 min stay varies

      • 3 bedrooms
      • sleeps 8
      • min stay varies
      • Child Friendly
      • Car not necessary
      • Air conditioning

      Price per night from

      $170

      Responds fast!
      avg. 3 hours 23 minutes

      Price per night from

      $170

        21

        Canalfront home w/ pool, dock & lanai - 2 blocks to the beach, dogs OK!

        Anna Maria Island / Anna Maria

        Anna Maria house

        3 6 min stay varies

        • 3 bedrooms
        • sleeps 6
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Car not necessary

        Price per night from

        $241

        Responds fast!
        avg. 3 hours 23 minutes

        Price per night from

        $241

          81

          Dog-friendly cottage w/ private heated pool - minutes from beaches & more!

          Anna Maria Island / Anna Maria

          Anna Maria house

          4 8 min stay varies

          • 4 bedrooms
          • sleeps 8
          • min stay varies
          • Swimming pool
          • Child Friendly
          • Car not necessary

          Price per night from

          $356

          Responds fast!
          avg. 3 hours 23 minutes

          Price per night from

          $356

            0

            Oceanfront dog-friendly home w/private pool & ocean view - right on the beach!

            Anna Maria Island / Anna Maria

            Anna Maria house

            3 6 min stay varies

            • 3 bedrooms
            • sleeps 6
            • min stay varies
            • Swimming pool
            • Child Friendly
            • Car not necessary

            Price per night from

            $535

            Responds fast!
            avg. 3 hours 23 minutes

            Price per night from

            $535

              0

              Spacious house w/ private yard & great location near the beach - dogs ok!

              Anna Maria Island / Anna Maria

              Anna Maria house

              2 6 min stay varies

              • 2 bedrooms
              • sleeps 6
              • min stay varies
              • Child Friendly
              • Car not necessary
              • Air conditioning

              Price per night from

              $170

              Responds fast!
              avg. 3 hours 23 minutes

              Price per night from

              $170

              (4) Excellent 

                22

                BEACHFRONT HOME, PRIVATE BEACH, DOGS STAY FREE, GREAT VIEWS, WALKING BEACH

                Anna Maria Island / Anna Maria

                Anna Maria house

                3 8 min stay varies

                • 3 bedrooms
                • sleeps 8
                • min stay varies
                • Child Friendly
                • Car not necessary
                • Air conditioning

                Price per night from

                $228

                Responds fast!
                avg. 1 hour 47 minutes

                Price per night from

                $228

                  43

                  Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!

                  Anna Maria Island / Anna Maria

                  Anna Maria house

                  3 6 min stay varies

                  • 3 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Swimming pool
                  • Child Friendly
                  • Car not necessary

                  Price per night from

                  $303

                  Responds fast!
                  avg. 3 hours 23 minutes

                  Price per night from

                  $303

                    0

                    Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

                    Anna Maria Island / Anna Maria

                    Anna Maria house

                    2 6 min stay varies

                    • 2 bedrooms
                    • sleeps 6
                    • min stay varies
                    • Swimming pool
                    • Child Friendly
                    • Car not necessary

                    Price per night from

                    $187

                    Responds fast!
                    avg. 3 hours 23 minutes

                    Price per night from

                    $187

                      56

                      Cute cottage with patio and amazing location near Pine St. and the beach

                      Anna Maria Island / Anna Maria

                      Anna Maria house

                      2 6 3 nights min

                      • 2 bedrooms
                      • sleeps 6
                      • 3 nights min
                      • Child Friendly
                      • Car not necessary
                      • Air conditioning

                      Price per night from

                      $213

                      Responds fast!
                      avg. 3 hours 23 minutes

                      Price per night from

                      $213

                        31

                        742 Jacaranda Rd

                        Anna Maria Island / Anna Maria

                        Anna Maria house

                        3 6 min stay varies

                        • 3 bedrooms
                        • sleeps 6
                        • min stay varies
                        • Child Friendly

                        Price per night from

                        $213

                        Price per night from

                        $213

                          58

                          Waterfront and dog-friendly home with private pool, dock, views, and lanai!

                          Anna Maria Island / Anna Maria

                          Anna Maria house

                          3 8 min stay varies

                          • 3 bedrooms
                          • sleeps 8
                          • min stay varies
                          • Swimming pool
                          • Child Friendly
                          • Car not necessary

                          Price per night from

                          $281

                          Responds fast!
                          avg. 3 hours 23 minutes

                          Price per night from

                          $281

                            185

                            Bright and cheery waterfront home with private pool and spa

                            Anna Maria Island / Anna Maria

                            Anna Maria house

                            3 6 min stay varies

                            • 3 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Swimming pool
                            • Child Friendly
                            • Car not necessary

                            Price per night from

                            $323

                            Responds fast!
                            avg. 3 hours 23 minutes

                            Price per night from

                            $323

                              0

                              Breezy canalfront home w/ pool & dock - 3 blocks to Bean Point Beach!

                              Anna Maria Island / Anna Maria

                              Anna Maria house

                              3 8 min stay varies

                              • 3 bedrooms
                              • sleeps 8
                              • min stay varies
                              • Swimming pool
                              • Child Friendly
                              • Car not necessary

                              Price per night from

                              $303

                              Responds fast!
                              avg. 3 hours 23 minutes

                              Price per night from

                              $303

                                0

                                Dog-friendly house with private pool, island views & nearby beach access!

                                Anna Maria Island / Anna Maria

                                Anna Maria house

                                2 4 min stay varies

                                • 2 bedrooms
                                • sleeps 4
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Car not necessary

                                Price per night from

                                $188

                                Responds fast!
                                avg. 3 hours 23 minutes

                                Price per night from

                                $188

                                (2) Excellent 

                                  39

                                  Dolphin Pointe

                                  Anna Maria Island / Anna Maria

                                  Anna Maria house

                                  3 8 7 nights min

                                  • 3 bedrooms
                                  • sleeps 8
                                  • 7 nights min
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Child Friendly

                                  Price per night from

                                  $295

                                  Responds fast!
                                  avg. 1 hour 10 minutes

                                  Price per night from

                                  $295

                                    74

                                    Charming house with private heated pool, patio, and grill - steps from beach

                                    Anna Maria Island / Anna Maria

                                    Anna Maria house

                                    3 6 min stay varies

                                    • 3 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Swimming pool
                                    • Child Friendly
                                    • Car not necessary

                                    Price per night from

                                    $241

                                    Responds fast!
                                    avg. 3 hours 23 minutes

                                    Price per night from

                                    $241

                                      29

                                      The Lime Door

                                      Anna Maria Island / Anna Maria

                                      Anna Maria house

                                      2 6 7 nights min

                                      • 2 bedrooms
                                      • sleeps 6
                                      • 7 nights min
                                      • Nearest beach 0.5 mi
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $279

                                      Price per night from

                                      $279

                                        80

                                        Sunny, dog-friendly cottage w/ a spacious patio and grill, steps from the beach!

                                        Anna Maria Island / Anna Maria

                                        Anna Maria house

                                        2 6 min stay varies

                                        • 2 bedrooms
                                        • sleeps 6
                                        • min stay varies
                                        • Child Friendly
                                        • Car not necessary
                                        • Air conditioning

                                        Price per night from

                                        $170

                                        Responds fast!
                                        avg. 3 hours 23 minutes

                                        Price per night from

                                        $170

                                        (4) Excellent 

                                          23

                                          19 Palms. Quaint Old-Florida Charm

                                          Anna Maria Island / Anna Maria

                                          Anna Maria house

                                          2 6 4 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 4 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          • Private garden

                                          Price per night from

                                          $172

                                          Responds fast!
                                          avg. 2 hours 35 minutes

                                          Price per night from

                                          $172

                                            70

                                            Luxury canal-front home with dock, pool & elevated deck - blocks to beach!

                                            Anna Maria Island / Anna Maria

                                            Anna Maria house

                                            4 8 7 nights min

                                            • 4 bedrooms
                                            • sleeps 8
                                            • 7 nights min
                                            • Swimming pool
                                            • Child Friendly
                                            • Car not necessary

                                            Price per night from

                                            $724

                                            Responds fast!
                                            avg. 3 hours 23 minutes

                                            Price per night from

                                            $724

                                            (35) Very Good 

                                            Certificate of Excellence

                                              46

                                              Gorgeous views,spectacular home!

                                              Anna Maria Island / Anna Maria

                                              Anna Maria house

                                              5 12 min stay varies

                                              • 5 bedrooms
                                              • sleeps 12
                                              • min stay varies
                                              • Beach / lakeside relaxation
                                              • Swimming pool
                                              • Child Friendly
                                              “Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.
                                              …see more

                                              Certificate of Excellence

                                              Price per night from

                                              $430

                                              Responds fast!
                                              avg. 36 minutes

                                              Price per night from

                                              $430

                                                0

                                                Dog-friendly condo w/ beautiful upstairs deck and grill, steps from the beach

                                                Anna Maria Island / Anna Maria

                                                Anna Maria house

                                                3 8 min stay varies

                                                • 3 bedrooms
                                                • sleeps 8
                                                • min stay varies
                                                • Child Friendly
                                                • Car not necessary
                                                • Air conditioning

                                                Price per night from

                                                $170

                                                Responds fast!
                                                avg. 3 hours 23 minutes

                                                Price per night from

                                                $170

                                                (6) Excellent 

                                                  23

                                                  Blue Heron Waterfront House Anna Maria island

                                                  Anna Maria Island / Anna Maria

                                                  Anna Maria house

                                                  3 6 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Beach / lakeside relaxation
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $286

                                                  Responds fast!
                                                  avg. 1 hour 13 minutes

                                                  Price per night from

                                                  $286

                                                  (2) Excellent 

                                                    0

                                                    Charming cottage w/ island views, entertainment & nearby beach access!

                                                    Anna Maria Island / Anna Maria

                                                    Anna Maria house

                                                    2 6 min stay varies

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • min stay varies
                                                    • Child Friendly
                                                    • Car not necessary
                                                    • Air conditioning

                                                    Price per night from

                                                    $152

                                                    Responds fast!
                                                    avg. 3 hours 23 minutes

                                                    Price per night from

                                                    $152

                                                      19

                                                      Beautiful luxury beach front condominium

                                                      Anna Maria Island / Anna Maria

                                                      Anna Maria condo

                                                      3 6 30 nights min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 30 nights min
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $722

                                                      Price per night from

                                                      $722

                                                        68

                                                        NEW LISTING! Oceanfront house with great views, easy beach access, and free WiFi

                                                        Anna Maria Island / Anna Maria

                                                        Anna Maria house

                                                        3 6 min stay varies

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Car not necessary

                                                        Price per night from

                                                        $338

                                                        Responds fast!
                                                        avg. 3 hours 23 minutes

                                                        Price per night from

                                                        $338

                                                        (9) Very Good 

                                                          32

                                                          744 Jacaranda Rd

                                                          Anna Maria Island / Anna Maria

                                                          Anna Maria house

                                                          3 6 min stay varies

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          “Nice getaway” Nice home! Large enough for family. Decks and heated pool were great!
                                                          …see more

                                                          Price per night from

                                                          $315

                                                          Price per night from

                                                          $315

                                                            33

                                                            Pelican Roost 505

                                                            Anna Maria Island / Anna Maria

                                                            Anna Maria house

                                                            5 10 7 nights min

                                                            • 5 bedrooms
                                                            • sleeps 10
                                                            • 7 nights min
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $532

                                                            Price per night from

                                                            $532

                                                              0

                                                              Well-equipped bungalow with private pool and deck - walk to beach, dogs ok!

                                                              Anna Maria Island / Anna Maria

                                                              Anna Maria house

                                                              3 8 7 nights min

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • 7 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Car not necessary

                                                              Price per night from

                                                              $284

                                                              Responds fast!
                                                              avg. 3 hours 23 minutes

                                                              Price per night from

                                                              $284

                                                              (12) Excellent 

                                                                53

                                                                Stay & Spoil yourself! Pool, Hot tub,Fish, Dock, Kayak* Steps to Gulfside beach!

                                                                Anna Maria Island / Anna Maria

                                                                Anna Maria house

                                                                4 8 min stay varies

                                                                • 4 bedrooms
                                                                • sleeps 8
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly
                                                                “Terrific home” Beautiful, comfortable home with lovely pool and just a short walk to gulf. Pictures don't fully capture how nice this home is! Our family had a wonderful week and hope to return again.
                                                                …see more

                                                                Price per night from

                                                                $413

                                                                Responds fast!
                                                                avg. 1 hour 30 minutes

                                                                Price per night from

                                                                $413

                                                                (3) Excellent 

                                                                  21

                                                                  Anna Maria Island "High End" Vacation Rental

                                                                  Anna Maria Island / Anna Maria

                                                                  Anna Maria house

                                                                  2 6 min stay varies

                                                                  • 2 bedrooms
                                                                  • sleeps 6
                                                                  • min stay varies
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $287

                                                                  Responds fast!
                                                                  avg. 2 hours 57 minutes

                                                                  Price per night from

                                                                  $287

                                                                    139

                                                                    NEW LISTING! Dog-friendly home w/private pool, near beach, shopping, dining

                                                                    Anna Maria Island / Anna Maria

                                                                    Anna Maria house

                                                                    2 6 min stay varies

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • min stay varies
                                                                    • Swimming pool
                                                                    • Child Friendly
                                                                    • Car not necessary

                                                                    Price per night from

                                                                    $164

                                                                    Responds fast!
                                                                    avg. 3 hours 23 minutes

                                                                    Price per night from

                                                                    $164

                                                                    (1) Excellent 

                                                                      24

                                                                      116 Maple Breeze

                                                                      Anna Maria Island / Anna Maria

                                                                      Anna Maria house

                                                                      4 7 7 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 7
                                                                      • 7 nights min
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $263

                                                                      Price per night from

                                                                      $263

                                                                        23

                                                                        Sea Haze Cottage - Gorgeous waterfront pool beachhouse

                                                                        Anna Maria Island / Anna Maria

                                                                        Anna Maria house

                                                                        3 6 7 nights min

                                                                        • 3 bedrooms
                                                                        • sleeps 6
                                                                        • 7 nights min
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $344

                                                                        Price per night from

                                                                        $344

                                                                          34

                                                                          High-end home w/ private pool & spa, courtyard, & floor-to-ceiling windows

                                                                          Anna Maria Island / Anna Maria

                                                                          Anna Maria house

                                                                          3 6 7 nights min

                                                                          • 3 bedrooms
                                                                          • sleeps 6
                                                                          • 7 nights min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $445

                                                                          Responds fast!
                                                                          avg. 3 hours 23 minutes

                                                                          Price per night from

                                                                          $445

                                                                            70

                                                                            Canalside home with dock and pool - blocks to the beach & free trolley!

                                                                            Anna Maria Island / Anna Maria

                                                                            Anna Maria house

                                                                            3 8 3 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 8
                                                                            • 3 nights min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Car not necessary

                                                                            Price per night from

                                                                            $378

                                                                            Responds fast!
                                                                            avg. 3 hours 23 minutes

                                                                            Price per night from

                                                                            $378

                                                                            (2) Excellent 

                                                                              25

                                                                              Sand Castle well appointed home steps from beaches

                                                                              Anna Maria Island / Anna Maria

                                                                              Anna Maria house

                                                                              3 8 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • min stay varies
                                                                              • Beach / lakeside relaxation
                                                                              • Nearest beach 0.1 mi
                                                                              • Swimming pool

                                                                              Price per night from

                                                                              $377

                                                                              Responds fast!
                                                                              avg. 1 hour 13 minutes

                                                                              Price per night from

                                                                              $377

                                                                              About Anna Maria

                                                                              Anna Maria, Florida

                                                                              The palm and hibiscus-lined streets of Anna Maria Island exude a relaxed, 1950s-style charm that attracts visitors all year round. Whether you come to laze on the white sandy beaches or explore all the area has to offer, you’re sure to find your perfect Anna Maria vacation rental with FlipKey.

                                                                              About Anna Maria

                                                                              Anna Maria Island was discovered by Native Americans and later by Spanish explorers in 1539. But the island wasn’t settled until the start of the 20th century, and it wasn’t until 1921 that a bridge was built, connecting the island to the mainland.

                                                                              Today, this relaxed island is home to three main towns: Bradenton Beach, Holmes Beach and Anna Maria. You’ll find some of the best beaches to the north and south of the island, and it’s just a one hour drive to Tampa, or two hours to Orlando and Disney.

                                                                              Dine on the freshest seafood, from Grouper, Shrimp, Mahi-Mahi and Lobster to Blue Crab and Red Snapper. You’ll also find great sushi, and excellent Italian and Mexican food on offer at seafront restaurants. Wash it all down with a glass of Florida orange juice – Tropicana is produced here in Bradenton!

                                                                              What to do

                                                                              There’s plenty to see and do here, but why not relax on the white sandy beaches that run the whole length of the island (7 miles)? The best beaches are Anna Maria Bayfront Park, and Southern Coquina Beach with its family-friendly facilities.

                                                                              Rent a boat or go on a charter fishing trip with the family, or explore the coastline in a kayak or boat. Diving, snorkeling and parasailing are all popular activities, or you could even go canoeing at Myakka State Park, where you’ll spot wild boar and alligators.

                                                                              A stroll around Anna Maria Island Museum is the opportunity to uncover local history, or people-watch at one of the island’s piers. Anna Maria City Pier is the place to see cruise ships leaving Tampa Bay and fishermen with their catch of the day, as well as stunning views of the Skyway Bridge.

                                                                              Top Anna Maria travel tips

                                                                              Anna Maria is just a one hour (53 miles) drive from Tampa International Airport, whilst Sarasota-Bradenton International Airport is 18 miles away.

                                                                              It’s easy to get around thanks to a free trolley service which runs from 6am-10pm daily, covering the whole of the island.

                                                                              Traffic limits of around 25mph in most areas mean that Anna Maria is a family-friendly destination, great for renting a bike or walking and exploring.

                                                                              Average temperatures of 80-90 degrees Fahrenheit ensure summer is the most popular season, but spring and fall are still warm (although evenings can be cooler).

                                                                              Sun, sea, sand, delicious seafood and plenty of outdoor activities for the whole family – what’s not to love?

                                                                              With over 1,000 cozy cottages, beachfront condos and villas to choose from, browse FlipKey for your Anna Maria vacation rental, today.