Vacation Rentals with Pool in Anna Maria

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Filtering by: Swimming pool

1,823 vacation 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

      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. 1 hour 42 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. 1 hour 42 minutes

        Price per night from

        $356

          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. 1 hour 42 minutes

          Price per night from

          $323

            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. 1 hour 58 minutes

            Price per night from

            $535

            (1) Very Good 

              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. 1 hour 42 minutes

              Price per night from

              $281

                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. 1 hour 42 minutes

                Price per night from

                $187

                (1) Excellent 

                  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. 1 hour 42 minutes

                  Price per night from

                  $241

                  (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

                    $294

                    Responds fast!
                    avg. 1 hour 10 minutes

                    Price per night from

                    $294

                      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. 1 hour 42 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. 1 hour 42 minutes

                        Price per night from

                        $188

                          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. 1 hour 42 minutes

                          Price per night from

                          $303

                          (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

                            $409

                            Responds fast!
                            avg. 1 hour 30 minutes

                            Price per night from

                            $409

                            (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

                              (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

                                $440

                                Responds fast!
                                avg. 36 minutes

                                Price per night from

                                $440

                                  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. 1 hour 4 minutes

                                  Price per night from

                                  $164

                                    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

                                    (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

                                      (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

                                          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. 1 hour 26 minutes

                                          Price per night from

                                          $724

                                          (5) Excellent 

                                            39

                                            5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

                                            Anna Maria Island / Anna Maria

                                            Anna Maria house

                                            3 8 3 nights min

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

                                            Price per night from

                                            $400

                                            Responds fast!
                                            avg. 1 hour 10 minutes

                                            Price per night from

                                            $400

                                              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. 1 hour 42 minutes

                                              Price per night from

                                              $284

                                                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. 1 hour 37 minutes

                                                Price per night from

                                                $445

                                                  21

                                                  Beachy Keen 408

                                                  Anna Maria Island / Anna Maria

                                                  Anna Maria house

                                                  3 6 min stay varies

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

                                                  Price per night from

                                                  $315

                                                  Price per night from

                                                  $315

                                                    0

                                                    Modern home with pool and balconies - steps to Bean Point Beach, dogs OK!

                                                    Anna Maria Island / Anna Maria

                                                    Anna Maria house

                                                    6 16 7 nights min

                                                    • 6 bedrooms
                                                    • sleeps 16
                                                    • 7 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Car not necessary

                                                    Price per night from

                                                    $535

                                                    Responds fast!
                                                    avg. 1 hour 42 minutes

                                                    Price per night from

                                                    $535

                                                      70

                                                      Casual, relaxing island home w/ a private pool - walk to dining & the beach!

                                                      Anna Maria Island / Anna Maria

                                                      Anna Maria house

                                                      3 7 min stay varies

                                                      • 3 bedrooms
                                                      • sleeps 7
                                                      • min stay varies
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Car not necessary

                                                      Price per night from

                                                      $215

                                                      Responds fast!
                                                      avg. 1 hour 58 minutes

                                                      Price per night from

                                                      $215

                                                        76

                                                        Incredible, dog-friendly house with private heated pool, close to 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

                                                        $368

                                                        Responds fast!
                                                        avg. 1 hour 37 minutes

                                                        Price per night from

                                                        $368

                                                          123

                                                          Luxury waterfront home w/ private pool and dock only three 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

                                                          $393

                                                          Responds fast!
                                                          avg. 1 hour 42 minutes

                                                          Price per night from

                                                          $393

                                                          (28) Very Good 

                                                          Certificate of Excellence

                                                            44

                                                            Crescent Wave

                                                            Anna Maria Island / Anna Maria

                                                            Anna Maria house

                                                            4 8 min stay varies

                                                            • 4 bedrooms
                                                            • sleeps 8
                                                            • min stay varies
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning
                                                            “Absolutely wonderful!!” This house is even better than it looks in the pictures .... everything you might want or need while on vacation is provided. It was extremely clean, and the location is perfect. The center across the street is a real bonus w
                                                            …see more

                                                            Certificate of Excellence

                                                            Price per night from

                                                            $229

                                                            Responds fast!
                                                            avg. 1 hour 20 minutes

                                                            Price per night from

                                                            $229

                                                              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. 1 hour 42 minutes

                                                              Price per night from

                                                              $378

                                                                152

                                                                Full duplex w/ shared heated pool and fenced backyard - dogs welcome!

                                                                Anna Maria Island / Anna Maria

                                                                Anna Maria house

                                                                6 12 min stay varies

                                                                • 6 bedrooms
                                                                • sleeps 12
                                                                • min stay varies
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Car not necessary

                                                                Price per night from

                                                                $481

                                                                Responds fast!
                                                                avg. 1 hour 42 minutes

                                                                Price per night from

                                                                $481

                                                                  23

                                                                  Beach To Bay Getaway

                                                                  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

                                                                  $280

                                                                  Price per night from

                                                                  $280

                                                                  (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

                                                                    $386

                                                                    Responds fast!
                                                                    avg. 1 hour 13 minutes

                                                                    Price per night from

                                                                    $386

                                                                      56

                                                                      Beautiful cottage w/ private pool - walk to the beach, dining, and Bayfront Park

                                                                      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

                                                                      $224

                                                                      Responds fast!
                                                                      avg. 1 hour 42 minutes

                                                                      Price per night from

                                                                      $224

                                                                        25

                                                                        Gladiolus on the Water

                                                                        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

                                                                        $292

                                                                        Price per night from

                                                                        $292

                                                                          32

                                                                          Freshly remodeled house with heated private pool and tropical style

                                                                          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

                                                                          $303

                                                                          Responds fast!
                                                                          avg. 1 hour 42 minutes

                                                                          Price per night from

                                                                          $303

                                                                          (1) Excellent 

                                                                            21

                                                                            Copacabana

                                                                            Anna Maria Island / Anna Maria

                                                                            Anna Maria house

                                                                            3 6 7 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $253

                                                                            Responds fast!
                                                                            avg. 1 hour 57 minutes

                                                                            Price per night from

                                                                            $253

                                                                              24

                                                                              The Oleander House

                                                                              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

                                                                              $360

                                                                              Price per night from

                                                                              $360