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324 vacation rentals
    48

    Beach Side Oasis W/ Pool and Short Walk to Restaurants and Bars on Bridge St.

    Anna Maria Island / Bradenton Beach

    Bradenton Beach condo

    1 5 min stay varies

    • 1 bedroom
    • sleeps 5
    • min stay varies
    • Swimming pool
    • Child Friendly
    • Air conditioning

    Price per night from

    $134

    Price per night from

    $134

    (3) Very Good 

      45

      APRIL 6-20 $400 OFF$ 5*Waterfront Canal Pool Home-Dock/Kayak/Bikes/FamilyFun/Pet

      Anna Maria Island / Holmes Beach

      Holmes Beach house

      2 6 7 nights min

      • 2 bedrooms
      • sleeps 6
      • 7 nights min
      • Beach / lakeside relaxation
      • Nearest beach 2 mi
      • Swimming pool

      Price per night from

      $220

      Price per night from

      $220

        32

        Villa Marisol

        Anna Maria Island / Anna Maria

        Anna Maria house

        4 10 7 nights min

        • 4 bedrooms
        • sleeps 10
        • 7 nights min
        • Car not necessary
        • Air conditioning

        Price per night from

        $1,005

        Price per night from

        $1,005

          12

          Bollinger Duplex, B

          Anna Maria Island / Holmes Beach

          Holmes Beach house

          1 6 7 nights min

          • 1 bedroom
          • sleeps 6
          • 7 nights min
          • Car not necessary
          • Air conditioning

          Price per night from

          $137

          Price per night from

          $137

            33

            Blue Dolphin Inn - All Units

            Anna Maria Island / Anna Maria

            Anna Maria house

            9 26 min stay varies

            • 9 bedrooms
            • sleeps 26
            • min stay varies
            • Swimming pool
            • Car not necessary
            • Air conditioning

            Price per night from

            $690

            Price per night from

            $690

              13

              Alamanda Villas 3

              Anna Maria Island / Holmes Beach

              Holmes Beach apartment

              1 4 min stay varies

              • 1 bedroom
              • sleeps 4
              • min stay varies
              • Swimming pool
              • Car not necessary
              • Air conditioning

              Price per night from

              $235

              Price per night from

              $235

                100

                Ss Salamander Both Units

                Anna Maria Island / Holmes Beach

                Holmes Beach house

                4 11 7 nights min

                • 4 bedrooms
                • sleeps 11
                • 7 nights min
                • Swimming pool
                • Car not necessary
                • Air conditioning

                Price per night from

                $426

                Price per night from

                $426

                  21

                  Blue Dolphin Inn - Skimmer Dow

                  Anna Maria Island / Anna Maria

                  Anna Maria house

                  2 6 min stay varies

                  • 2 bedrooms
                  • sleeps 6
                  • min stay varies
                  • Swimming pool
                  • Car not necessary
                  • Air conditioning

                  Price per night from

                  $167

                  Price per night from

                  $167

                    32

                    Walk to the Beach and More from this Renovated Anna Maria Island Rental

                    Anna Maria Island / Holmes Beach

                    Holmes Beach condo

                    2 6 min stay varies

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

                    Price per night from

                    $115

                    Price per night from

                    $115

                      32

                      Updated and within Walking Distance to Uncrowded Beach Stores and Restaurants

                      Anna Maria Island / Holmes Beach

                      Holmes Beach condo

                      2 6 min stay varies

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

                      Price per night from

                      $115

                      Price per night from

                      $115

                        19

                        Seaside Beach House 205

                        Anna Maria Island / Holmes Beach

                        Holmes Beach apartment

                        2 4 7 nights min

                        • 2 bedrooms
                        • sleeps 4
                        • 7 nights min
                        • Swimming pool
                        • Car not necessary
                        • Air conditioning

                        Price per night from

                        $258

                        Price per night from

                        $258

                          13

                          MI Happy Place Sand Castle 1

                          Anna Maria Island / Holmes Beach

                          Holmes Beach house

                          2 6 min stay varies

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

                          Price per night from

                          $197

                          Price per night from

                          $197

                            12

                            Valhalla Up And Down

                            Anna Maria Island / Holmes Beach

                            Holmes Beach house

                            5 13 7 nights min

                            • 5 bedrooms
                            • sleeps 13
                            • 7 nights min
                            • Car not necessary
                            • Air conditioning
                            • Pet Friendly

                            Price per night from

                            $623

                            Price per night from

                            $623

                              17

                              Blue Dolphin Inn - Ibis

                              Anna Maria Island / Anna Maria

                              Anna Maria house

                              2 6 min stay varies

                              • 2 bedrooms
                              • sleeps 6
                              • min stay varies
                              • Swimming pool
                              • Car not necessary
                              • Air conditioning

                              Price per night from

                              $168

                              Price per night from

                              $168

                                22

                                A Wright Place

                                Anna Maria Island / Holmes Beach

                                Holmes Beach house

                                2 6 7 nights min

                                • 2 bedrooms
                                • sleeps 6
                                • 7 nights min
                                • Swimming pool
                                • Car not necessary
                                • Air conditioning

                                Price per night from

                                $189

                                Price per night from

                                $189

                                  28

                                  Anna Cabana Beach House

                                  Anna Maria Island / Holmes Beach

                                  Holmes Beach house

                                  2 6 7 nights min

                                  • 2 bedrooms
                                  • sleeps 6
                                  • 7 nights min
                                  • Swimming pool
                                  • Car not necessary
                                  • Air conditioning

                                  Price per night from

                                  $245

                                  Price per night from

                                  $245

                                    31

                                    Dolphin Dance, Both Units

                                    Anna Maria Island / Bradenton Beach

                                    Bradenton Beach house

                                    4 12 7 nights min

                                    • 4 bedrooms
                                    • sleeps 12
                                    • 7 nights min
                                    • Car not necessary
                                    • Air conditioning

                                    Price per night from

                                    $377

                                    Price per night from

                                    $377

                                      13

                                      MI Happy Place Sand Dollar 2

                                      Anna Maria Island / Holmes Beach

                                      Holmes Beach house

                                      2 6 min stay varies

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

                                      Price per night from

                                      $197

                                      Price per night from

                                      $197

                                        12

                                        Alamanda Villas 7

                                        Anna Maria Island / Holmes Beach

                                        Holmes Beach apartment

                                        1 4 min stay varies

                                        • 1 bedroom
                                        • sleeps 4
                                        • min stay varies
                                        • Swimming pool
                                        • Car not necessary
                                        • Air conditioning

                                        Price per night from

                                        $235

                                        Price per night from

                                        $235

                                          21

                                          Cove At Sandy Pointe 111

                                          Anna Maria Island / Holmes Beach

                                          Holmes Beach apartment

                                          3 6 7 nights min

                                          • 3 bedrooms
                                          • sleeps 6
                                          • 7 nights min
                                          • Swimming pool
                                          • Car not necessary
                                          • Air conditioning

                                          Price per night from

                                          $156

                                          Price per night from

                                          $156

                                            23

                                            Azure Seas Home 779

                                            Anna Maria Island / Anna Maria

                                            Anna Maria house

                                            3 8 7 nights min

                                            • 3 bedrooms
                                            • sleeps 8
                                            • 7 nights min
                                            • Car not necessary
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $455

                                            Price per night from

                                            $455

                                              18

                                              Waters Edge 210s

                                              Anna Maria Island / Holmes Beach

                                              Holmes Beach apartment

                                              2 6 28 nights min

                                              • 2 bedrooms
                                              • sleeps 6
                                              • 28 nights min
                                              • Swimming pool
                                              • Car not necessary
                                              • Air conditioning

                                              Price per night from

                                              $273

                                              Price per night from

                                              $273

                                                17

                                                Shell Cove 9

                                                Anna Maria Island / Bradenton Beach

                                                Bradenton Beach apartment

                                                2 6 min stay varies

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

                                                Price per night from

                                                $250

                                                Price per night from

                                                $250

                                                  24

                                                  Ocean Park Terrace 202

                                                  Anna Maria Island / Holmes Beach

                                                  Holmes Beach apartment

                                                  2 5 14 nights min

                                                  • 2 bedrooms
                                                  • sleeps 5
                                                  • 14 nights min
                                                  • Swimming pool
                                                  • Car not necessary
                                                  • Air conditioning

                                                  Price per night from

                                                  $394

                                                  Price per night from

                                                  $394

                                                    39

                                                    Fountainhead Condo 3

                                                    Anna Maria Island / Holmes Beach

                                                    Holmes Beach apartment

                                                    2 6 7 nights min

                                                    • 2 bedrooms
                                                    • sleeps 6
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Car not necessary
                                                    • Air conditioning

                                                    Price per night from

                                                    $167

                                                    Price per night from

                                                    $167

                                                      39

                                                      Bollinger Duplex Both Sides

                                                      Anna Maria Island / Holmes Beach

                                                      Holmes Beach house

                                                      3 14 7 nights min

                                                      • 3 bedrooms
                                                      • sleeps 14
                                                      • 7 nights min
                                                      • Car not necessary
                                                      • Air conditioning

                                                      Price per night from

                                                      $277

                                                      Price per night from

                                                      $277

                                                        17

                                                        Sandy Pointe 210

                                                        Anna Maria Island / Holmes Beach

                                                        Holmes Beach apartment

                                                        2 6 7 nights min

                                                        • 2 bedrooms
                                                        • sleeps 6
                                                        • 7 nights min
                                                        • Swimming pool
                                                        • Car not necessary
                                                        • Air conditioning

                                                        Price per night from

                                                        $152

                                                        Price per night from

                                                        $152

                                                          18

                                                          Anna Maria Escape

                                                          Anna Maria Island / Anna Maria

                                                          Anna Maria house

                                                          2 8 7 nights min

                                                          • 2 bedrooms
                                                          • sleeps 8
                                                          • 7 nights min
                                                          • Car not necessary
                                                          • Air conditioning
                                                          • Pet Friendly

                                                          Price per night from

                                                          $320

                                                          Price per night from

                                                          $320

                                                            22

                                                            Fountainhead Condo 4

                                                            Anna Maria Island / Holmes Beach

                                                            Holmes Beach apartment

                                                            2 4 7 nights min

                                                            • 2 bedrooms
                                                            • sleeps 4
                                                            • 7 nights min
                                                            • Swimming pool
                                                            • Car not necessary
                                                            • Air conditioning

                                                            Price per night from

                                                            $167

                                                            Price per night from

                                                            $167

                                                              23

                                                              Blue Dolphin Inn - Flamingo Up

                                                              Anna Maria Island / Anna Maria

                                                              Anna Maria house

                                                              3 8 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Car not necessary
                                                              • Air conditioning

                                                              Price per night from

                                                              $228

                                                              Price per night from

                                                              $228

                                                                32

                                                                Expansive Views, Walk to Beach and Grocer, Anna Maria Island Vacation Rental

                                                                Anna Maria Island / Holmes Beach

                                                                Holmes Beach condo

                                                                2 5 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 5
                                                                • min stay varies
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $103

                                                                Price per night from

                                                                $103

                                                                  16

                                                                  Absolutely Perfect

                                                                  Anna Maria Island / Holmes Beach

                                                                  Holmes Beach house

                                                                  4 8 7 nights min

                                                                  • 4 bedrooms
                                                                  • sleeps 8
                                                                  • 7 nights min
                                                                  • Swimming pool
                                                                  • Car not necessary
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $1,005

                                                                  Price per night from

                                                                  $1,005

                                                                  (1) Excellent 

                                                                    18

                                                                    Gulf Sands 201

                                                                    Anna Maria Island / Holmes Beach

                                                                    Holmes Beach apartment

                                                                    2 6 7 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • 7 nights min
                                                                    • Swimming pool
                                                                    • Car not necessary
                                                                    • Air conditioning

                                                                    Price per night from

                                                                    $311

                                                                    Price per night from

                                                                    $311

                                                                      21

                                                                      Four Beach Lovers All Units

                                                                      Anna Maria Island / Holmes Beach

                                                                      Holmes Beach house

                                                                      4 16 7 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 16
                                                                      • 7 nights min
                                                                      • Car not necessary
                                                                      • Air conditioning
                                                                      • Pet Friendly

                                                                      Price per night from

                                                                      $795

                                                                      Price per night from

                                                                      $795

                                                                        15

                                                                        Cyndy's Beach House

                                                                        Anna Maria Island / Holmes Beach

                                                                        Holmes Beach house

                                                                        2 4 28 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 4
                                                                        • 28 nights min
                                                                        • Child Friendly
                                                                        • Car not necessary
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $164

                                                                        Price per night from

                                                                        $164

                                                                          13

                                                                          MI Happy Place Sea Turtle 4

                                                                          Anna Maria Island / Holmes Beach

                                                                          Holmes Beach house

                                                                          2 4 min stay varies

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

                                                                          Price per night from

                                                                          $197

                                                                          Price per night from

                                                                          $197

                                                                            13

                                                                            Alamanda Villas 5

                                                                            Anna Maria Island / Holmes Beach

                                                                            Holmes Beach apartment

                                                                            1 4 min stay varies

                                                                            • 1 bedroom
                                                                            • sleeps 4
                                                                            • min stay varies
                                                                            • Swimming pool
                                                                            • Car not necessary
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $236

                                                                            Price per night from

                                                                            $236

                                                                              16

                                                                              Sunset View Home #100

                                                                              Anna Maria Island / Bradenton Beach

                                                                              Bradenton Beach house

                                                                              3 8 7 nights min

                                                                              • 3 bedrooms
                                                                              • sleeps 8
                                                                              • 7 nights min
                                                                              • Swimming pool
                                                                              • Car not necessary
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $339

                                                                              Price per night from

                                                                              $339