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325 vacation rentals
    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

    $1,010

    Price per night from

    $1,010

      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

      $694

      Price per night from

      $694

        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

        $168

        Price per night from

        $168

          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

            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

            $457

            Price per night from

            $457

              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

              $322

              Price per night from

              $322

                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

                $229

                Price per night from

                $229

                  28

                  Blue Dolphin Inn - Heron Up

                  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

                  $213

                  Price per night from

                  $213

                  (23) Very Good 

                    49

                    Anna Maria Island Nantucket

                    Anna Maria Island / Anna Maria

                    Anna Maria house

                    4 8 28 nights min

                    • 4 bedrooms
                    • sleeps 8
                    • 28 nights min
                    • Beach / lakeside relaxation
                    • Nearest beach 0.2 mi
                    • Swimming pool
                    “"Great vacation home"” open, spacious, comfy home. very clean, beautifully decorated. everything you need was there( paper products, spices, dishes, etc.). great for families with children. game room, pool, bikes, all beach necessities.
                    …see more

                    Price per night from

                    $201

                    Responds fast!
                    avg. 2 hours 37 minutes

                    Price per night from

                    $201

                    Great rentals within 20 miles that match your search

                    Distance approx 9.22 km from Anna Maria

                    (3) Excellent 

                      19

                      Paradise Retreat -- Need We Say More

                      Southwest Gulf Coast / Bradenton

                      Bradenton house

                      3 6 1 night min

                      • 3 bedrooms
                      • sleeps 6
                      • 1 night min
                      • Beach / lakeside relaxation
                      • Swimming pool
                      • Child Friendly

                      Price per night from

                      $135

                      Responds fast!
                      avg. 1 hour 43 minutes

                      Price per night from

                      $135

                      Distance approx 17.05 km from Anna Maria

                        19

                        Heritage Harbour 2 bed, 2 bath Villa backs to Lake in gated golf community!!

                        Southwest Gulf Coast / Bradenton

                        Bradenton house

                        2 6 20 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 20 nights min
                        • Swimming pool
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $126

                        Responds fast!
                        avg. 2 hours 8 minutes

                        Price per night from

                        $126

                        Distance approx 12.56 km from Anna Maria

                        (1) Excellent 

                          17

                          Spacious clean quiet home facing the Boca Ciega Bay in Isla del Sol

                          Florida / St. Pete Beach

                          St. Pete Beach apartment

                          2 6 min stay varies

                          • 2 bedrooms
                          • sleeps 6
                          • min stay varies
                          • Nearest beach 3 mi
                          • Child Friendly
                          • Air conditioning

                          Price per night from

                          $74

                          Responds fast!
                          avg. 1 hour 21 minutes

                          Price per night from

                          $74

                          Distance approx 9.2 km from Anna Maria

                          (25) Excellent 

                            30

                            Shorewalk 'Turtle Cove': A+ Rated Resort Condo: Pools,spas, beach and IMG

                            Southwest Gulf Coast / Bradenton

                            Bradenton condo

                            2 4 min stay varies

                            • 2 bedrooms
                            • sleeps 4
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Nearest beach 10 mi
                            • Swimming pool
                            “So Beautiful!” When we checked in to this wonderful ground floor villa, we were amazed. The photos online don't do this place justice - it is sooo beautiful and so comfortable!!!
                            …see more

                            Price per night from

                            $102

                            Responds fast!
                            avg. 45 minutes

                            Price per night from

                            $102

                            Distance approx 12.91 km from Anna Maria

                            (2) Excellent 

                              26

                              Waterfront Villa Isla Del Sol St Petersburg FL

                              Florida / St. Petersburg

                              St. Petersburg villa

                              2 4 min stay varies

                              • 2 bedrooms
                              • sleeps 4
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Nearest beach 2 mi
                              • Swimming pool
                              “Fantastic getaway” We stayed the month of February and had a wonderful experience. Not only was Will great to work with but the location was fabulous, the views spectacular, and the entire condo was very comfortable to stay in. So much to do or just
                              …see more

                              Price per night from

                              $154

                              Price per night from

                              $154

                              Distance approx 16.49 km from Anna Maria

                                22

                                River Strand 43

                                Southwest Gulf Coast / Bradenton

                                Bradenton house

                                3 6 min stay varies

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

                                Price per night from

                                $193

                                Price per night from

                                $193

                                Distance approx 9.18 km from Anna Maria

                                  24

                                  SHOREWALK VACATION VILLA

                                  Southwest Gulf Coast / Bradenton

                                  Bradenton apartment

                                  2 4 5 nights min

                                  • 2 bedrooms
                                  • sleeps 4
                                  • 5 nights min
                                  • Beach / lakeside relaxation
                                  • Nearest beach 15 mi
                                  • Swimming pool

                                  Price per night from

                                  $146

                                  Price per night from

                                  $146

                                  Distance approx 15.63 km from Anna Maria

                                    11

                                    Charming 2 Bedroom House, Fenced and Private

                                    Southwest Gulf Coast / Sarasota

                                    Sarasota house

                                    2 6 7 nights min

                                    • 2 bedrooms
                                    • sleeps 6
                                    • 7 nights min
                                    • Child Friendly
                                    • Air conditioning
                                    • Ask about pets

                                    Price per night from

                                    $228

                                    Responds fast!
                                    avg. 3 hours 8 minutes

                                    Price per night from

                                    $228

                                    Distance approx 9.03 km from Anna Maria

                                    (4) Excellent 

                                      16

                                      Shorewalk Condo, Newly Decorated w/lake view

                                      Southwest Gulf Coast / Bradenton

                                      Bradenton condo

                                      2 4 7 nights min

                                      • 2 bedrooms
                                      • sleeps 4
                                      • 7 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 5 mi
                                      • Child Friendly
                                      “Very relaxing and clean condo with wonderful amenities and stores close by!!” We had a wonderful time and enjoyed all that the condo had to offer. We found it really clean and decorated in true Florida fashion. Loved the place and will return!!
                                      …see more

                                      Price per night from

                                      $91

                                      Responds fast!
                                      avg. 2 hours 59 minutes

                                      Price per night from

                                      $91

                                      Distance approx 18.73 km from Anna Maria

                                        24

                                        Sarasota, Beaches, Lido, Down Town, Siesta

                                        Southwest Gulf Coast / Sarasota

                                        Sarasota house

                                        4 10 7 nights min

                                        • 4 bedrooms
                                        • sleeps 10
                                        • 7 nights min
                                        • Nearest beach 8 mi
                                        • Swimming pool
                                        • Child Friendly

                                        Price per night from

                                        $260

                                        Price per night from

                                        $260

                                        Distance approx 17.97 km from Anna Maria

                                          19

                                          Centrally Located Condo with Golf Course View

                                          Florida / Lakewood Ranch

                                          Lakewood Ranch condo

                                          2 6 30 nights min

                                          • 2 bedrooms
                                          • sleeps 6
                                          • 30 nights min
                                          • Swimming pool
                                          • Child Friendly
                                          • Air conditioning

                                          Price per night from

                                          $85

                                          Price per night from

                                          $85

                                          Distance approx 12.31 km from Anna Maria

                                            6

                                            Newly available including Jan and Feb 2018

                                            Florida / St. Pete Beach

                                            St. Pete Beach apartment

                                            2 4 7 nights min

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

                                            Price per night from

                                            $130

                                            Price per night from

                                            $130

                                            Distance approx 16.07 km from Anna Maria

                                            (1) Excellent 

                                              40

                                              Riley's Retreat, 2 Bedroom Water Front with Boat Dock and Beach Access

                                              Florida / Treasure Island

                                              Treasure Island apartment

                                              2 4 3 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 3 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0.1 mi
                                              • Car not necessary

                                              Price per night from

                                              $257

                                              Responds fast!
                                              avg. 59 minutes

                                              Price per night from

                                              $257

                                              Distance approx 12.38 km from Anna Maria

                                                8

                                                Panoramic views from this lovely 9th floor waterfront unit

                                                Florida / St. Pete Beach

                                                St. Pete Beach condo

                                                2 4 14 nights min

                                                • 2 bedrooms
                                                • sleeps 4
                                                • 14 nights min
                                                • Child Friendly

                                                Price per night from

                                                $147

                                                Price per night from

                                                $147

                                                Distance approx 19.39 km from Anna Maria

                                                  19

                                                  Tropical Charm - Beautifully furnished, pool

                                                  Southwest Gulf Coast / Sarasota

                                                  Sarasota condo

                                                  2 5 90 nights min

                                                  • 2 bedrooms
                                                  • sleeps 5
                                                  • 90 nights min
                                                  • Nearest beach 9 mi
                                                  • Swimming pool
                                                  • Child Friendly

                                                  Price per night from

                                                  $95

                                                  Price per night from

                                                  $95

                                                  Distance approx 17.92 km from Anna Maria

                                                  (5) Excellent 

                                                    32

                                                    SARASOTA : Paradise for golfers and beach lovers

                                                    Southwest Gulf Coast / Sarasota

                                                    Sarasota house

                                                    4 8 30 nights min

                                                    • 4 bedrooms
                                                    • sleeps 8
                                                    • 30 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 13 mi
                                                    • Swimming pool

                                                    Price per night from

                                                    $265

                                                    Price per night from

                                                    $265

                                                    Distance approx 13.91 km from Anna Maria

                                                    (3) Excellent 

                                                      24

                                                      Longboat Key Bayfront condo in Bay Isles

                                                      Florida / Longboat Key

                                                      Longboat Key condo

                                                      2 4 90 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 90 nights min
                                                      • Child Friendly

                                                      Price per night from

                                                      $209

                                                      Price per night from

                                                      $209

                                                      Distance approx 9 km from Anna Maria

                                                        12

                                                        Paradise on the Bay

                                                        Florida / Palmetto

                                                        Palmetto apartment

                                                        2 4 60 nights min

                                                        • 2 bedrooms
                                                        • sleeps 4
                                                        • 60 nights min
                                                        • Beach / lakeside relaxation
                                                        • Nearest beach 32 mi
                                                        • Swimming pool

                                                        Price per night from

                                                        $106

                                                        Price per night from

                                                        $106

                                                        Distance approx 12.39 km from Anna Maria

                                                          24

                                                          Beautiful Island on Boca Ciega Bay & The Beach

                                                          Florida / St. Petersburg

                                                          St. Petersburg condo

                                                          2 4 14 nights min

                                                          • 2 bedrooms
                                                          • sleeps 4
                                                          • 14 nights min
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 0.8 mi
                                                          • Swimming pool

                                                          Price per night from

                                                          $114

                                                          Price per night from

                                                          $114

                                                          Distance approx 1.56 km from Anna Maria Show on Map

                                                            16

                                                            Pool Party North Side

                                                            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

                                                            $196

                                                            Price per night from

                                                            $196

                                                            Distance approx 18.1 km from Anna Maria

                                                              29

                                                              North Madeira # 212

                                                              Florida / Treasure Island

                                                              Treasure Island condo

                                                              2 4 7 nights min

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

                                                              Price per night from

                                                              $271

                                                              Price per night from

                                                              $271

                                                              Distance approx 19.85 km from Anna Maria

                                                                21

                                                                AAA Accommodation in The Meadows - Sarasota

                                                                Florida / Fruitville

                                                                Fruitville condo

                                                                2 6 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 6
                                                                • min stay varies
                                                                • Nearest beach 14 mi
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $101

                                                                Responds fast!
                                                                avg. 1 hour 3 minutes

                                                                Price per night from

                                                                $101

                                                                Distance approx 9.76 km from Anna Maria

                                                                  28

                                                                  Haagen's Turtle Nest

                                                                  Southwest Gulf Coast / Bradenton

                                                                  Bradenton apartment

                                                                  2 5 7 nights min

                                                                  • 2 bedrooms
                                                                  • sleeps 5
                                                                  • 7 nights min
                                                                  • Beach / lakeside relaxation
                                                                  • Nearest beach 3 mi
                                                                  • Swimming pool

                                                                  Price per night from

                                                                  $125

                                                                  Price per night from

                                                                  $125

                                                                  Distance approx 10.15 km from Anna Maria

                                                                    16

                                                                    IMG golf private 3 bed home

                                                                    Southwest Gulf Coast / Bradenton

                                                                    Bradenton house

                                                                    3 4 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 4
                                                                    • min stay varies
                                                                    • Nearest beach 10 mi
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $158

                                                                    Price per night from

                                                                    $158

                                                                    Distance approx 17.26 km from Anna Maria

                                                                      17

                                                                      Sarasota Villa

                                                                      Southwest Gulf Coast / Sarasota

                                                                      Sarasota villa

                                                                      3 6 7 nights min

                                                                      • 3 bedrooms
                                                                      • sleeps 6
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0 mi
                                                                      • Swimming pool

                                                                      Price per night from

                                                                      $116

                                                                      Price per night from

                                                                      $116

                                                                      Distance approx 17.38 km from Anna Maria

                                                                      (1) Excellent 

                                                                        26

                                                                        GULF VIEW, TWO x 2BR SUITES, BEACHFRONT BLDG, POOLS, HOT TUB, GYM, FREE PARKING

                                                                        Florida / Treasure Island

                                                                        Treasure Island apartment

                                                                        4 12 min stay varies

                                                                        • 4 bedrooms
                                                                        • sleeps 12
                                                                        • min stay varies
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $500

                                                                        Price per night from

                                                                        $500

                                                                        Distance approx 11.76 km from Anna Maria

                                                                          26

                                                                          22-2 BeachHouse Sleeps6 Beauty&Redone w/WiFI&Bikes

                                                                          St. Pete Beach / Pass-a-Grille

                                                                          St. Pete Beach cottage

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Beach / lakeside relaxation
                                                                          • Nearest beach 1 mi
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $285

                                                                          Price per night from

                                                                          $285

                                                                          Distance approx 9.22 km from Anna Maria

                                                                            31

                                                                            Luxury lakefront Sunshine Shorewalk 2B condo, 1 km. IMG Academy, 10 min to beach

                                                                            Southwest Gulf Coast / Bradenton

                                                                            Bradenton villa

                                                                            2 4 7 nights min

                                                                            • 2 bedrooms
                                                                            • sleeps 4
                                                                            • 7 nights min
                                                                            • Swimming pool
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $85

                                                                            Price per night from

                                                                            $85

                                                                            Distance approx 2.02 km from Anna Maria Show on Map

                                                                              38

                                                                              Bay Boulevard (ANN765)

                                                                              Anna Maria Island / Holmes Beach

                                                                              Holmes Beach house

                                                                              3 6 7 nights min

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

                                                                              Price per night from

                                                                              $384

                                                                              Price per night from

                                                                              $384