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341 vacation rentals
    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

    $138

    Price per night from

    $138

    (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

      $222

      Price per night from

      $222

        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

        $428

        Price per night from

        $428

          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

          $236

          Price per night from

          $236

            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

            $260

            Price per night from

            $260

              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

              $116

              Price per night from

              $116

                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

                $198

                Price per night from

                $198

                  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

                  $627

                  Price per night from

                  $627

                    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

                    $190

                    Price per night from

                    $190

                      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

                      $116

                      Price per night from

                      $116

                        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

                        $236

                        Price per night from

                        $236

                          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

                          $198

                          Price per night from

                          $198

                            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

                            $247

                            Price per night from

                            $247

                              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

                              $158

                              Price per night from

                              $158

                                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

                                $275

                                Price per night from

                                $275

                                  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

                                  $153

                                  Price per night from

                                  $153

                                    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

                                      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

                                      $168

                                      Price per night from

                                      $168

                                        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

                                        $279

                                        Price per night from

                                        $279

                                          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

                                          $168

                                          Price per night from

                                          $168

                                            17

                                            Seacrest II Condos 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

                                            $161

                                            Price per night from

                                            $161

                                              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

                                              $1,010

                                              Price per night from

                                              $1,010

                                                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

                                                  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

                                                  $166

                                                  Price per night from

                                                  $166

                                                    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

                                                    $198

                                                    Price per night from

                                                    $198

                                                      11

                                                      Anna Maria Beach Place, Unit 6

                                                      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

                                                      $176

                                                      Price per night from

                                                      $176

                                                        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

                                                        $800

                                                        Price per night from

                                                        $800

                                                          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

                                                          (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

                                                            $313

                                                            Price per night from

                                                            $313

                                                              14

                                                              Alamanda Villas 4

                                                              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

                                                              $237

                                                              Price per night from

                                                              $237

                                                                35

                                                                Canal-front, dog-friendly home with private heated pool, hot tub, outdoor bar

                                                                Anna Maria Island / Holmes Beach

                                                                Holmes Beach house

                                                                4 10 28 nights min

                                                                • 4 bedrooms
                                                                • sleeps 10
                                                                • 28 nights min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Car not necessary

                                                                Price per night from

                                                                $298

                                                                Price per night from

                                                                $298

                                                                  17

                                                                  Jukes Beach House

                                                                  Anna Maria Island / Holmes Beach

                                                                  Holmes Beach house

                                                                  2 4 7 nights min

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

                                                                  Price per night from

                                                                  $322

                                                                  Price per night from

                                                                  $322

                                                                    12

                                                                    Alamanda Villas 2

                                                                    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

                                                                    $237

                                                                    Price per night from

                                                                    $237

                                                                      18

                                                                      Seaside Beach House 101

                                                                      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

                                                                      $414

                                                                      Price per night from

                                                                      $414

                                                                        26

                                                                        Seabreeze Condo B

                                                                        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

                                                                        $168

                                                                        Price per night from

                                                                        $168

                                                                          37

                                                                          MI Happy Place-All units

                                                                          Anna Maria Island / Holmes Beach

                                                                          Holmes Beach house

                                                                          8 22 min stay varies

                                                                          • 8 bedrooms
                                                                          • sleeps 22
                                                                          • min stay varies
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $742

                                                                          Price per night from

                                                                          $742

                                                                            17

                                                                            Bollinger Duplex, A

                                                                            Anna Maria Island / Holmes Beach

                                                                            Holmes Beach house

                                                                            2 8 7 nights min

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

                                                                            Price per night from

                                                                            $334

                                                                            Price per night from

                                                                            $334

                                                                              7

                                                                              Four Beach Lovers 2

                                                                              Anna Maria Island / Holmes Beach

                                                                              Holmes Beach house

                                                                              1 4 7 nights min

                                                                              • 1 bedroom
                                                                              • sleeps 4
                                                                              • 7 nights min
                                                                              • Car not necessary
                                                                              • Air conditioning
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $259

                                                                              Price per night from

                                                                              $259