Heritage Harbor Rentals

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2,737 Houses

    26

    River Strand Golf and Country Club Resort

    Bradenton / Heritage Harbor

    Bradenton condo

    2 4 30 nights min

    • 2 bedrooms
    • sleeps 4
    • 30 nights min
    • Beach / lakeside relaxation
    • Swimming pool
    • Ask about children

    Price per night from

    $152

    Responds fast!
    avg. 25 minutes

    Price per night from

    $152

    (4) Excellent 

      21

      River Strand Luxury Condo-Tennis & Golf Community

      Bradenton / Heritage Harbor

      Bradenton condo

      2 5 min stay varies

      • 2 bedrooms
      • sleeps 5
      • min stay varies
      • Nearest beach 20 mi
      • Swimming pool
      • Child Friendly

      Price per night from

      $66

      Responds fast!
      avg. 50 minutes

      Price per night from

      $66

      Great rentals within 20 miles that match your search

      Distance approx 17.77 km from Heritage Harbor

        40

        Large 1300sqft 2BR2BA 4th Floor Siesta Key Crescent Beach WiFi No Road to Cross

        Florida / Siesta Key

        Siesta Key apartment

        2 5 min stay varies

        • 2 bedrooms
        • sleeps 5
        • min stay varies
        • Nearest beach 0.1 mi
        • Swimming pool
        • Child Friendly

        Price per night from

        $161

        Price per night from

        $161

        Distance approx 15.24 km from Heritage Harbor

          34

          Hibiscus ( 2-Bedroom Condo )

          Anna Maria Island / Bradenton Beach

          Bradenton Beach house

          2 6 7 nights min

          • 2 bedrooms
          • sleeps 6
          • 7 nights min
          • Car not necessary

          Price per night from

          $303

          Price per night from

          $303

          Distance approx 13.31 km from Heritage Harbor

          (9) Excellent 

            27

            Paradise Found

            Southwest Gulf Coast / Bradenton

            Bradenton apartment

            2 4 4 nights min

            • 2 bedrooms
            • sleeps 4
            • 4 nights min
            • Beach / lakeside relaxation
            • Nearest beach 2 mi
            • Air conditioning

            Price per night from

            $131

            Responds fast!
            avg. 2 hours 53 minutes

            Price per night from

            $131

            Distance approx 17.8 km from Heritage Harbor

              26

              Bright 2 bedroom home 10 minutes to Siesta Key - Lots of restaurants nearby

              Florida / Gulf Gate Branch

              Gulf Gate Branch house

              2 4 min stay varies

              • 2 bedrooms
              • sleeps 4
              • min stay varies
              • Child Friendly
              • Air conditioning

              Price per night from

              $96

              Responds fast!
              avg. 3 hours 25 minutes

              Price per night from

              $96

              Distance approx 17.01 km from Heritage Harbor

              (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.

                Price per night from

                $199

                Responds fast!
                avg. 2 hours 43 minutes

                Price per night from

                $199

                Distance approx 15.33 km from Heritage Harbor

                (1) Excellent 

                  26

                  The Beach

                  Florida / Ruskin

                  Ruskin townhouse

                  2 5 4 nights min

                  • 2 bedrooms
                  • sleeps 5
                  • 4 nights min
                  • Beach / lakeside relaxation
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $171

                  Responds fast!
                  avg. 3 hours 41 minutes

                  Price per night from

                  $171

                  Distance approx 18.3 km from Heritage Harbor

                  (1) Very Good 

                    16

                    Walk to the Bay!

                    Florida / St. Petersburg

                    St. Petersburg house

                    3 7 3 nights min

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

                    Price per night from

                    $171

                    Responds fast!
                    avg. 47 minutes

                    Price per night from

                    $171

                    Distance approx 14.97 km from Heritage Harbor

                      4

                      Pirates Pointe Resort 2 Bedroom

                      Florida / Ruskin

                      Ruskin cottage

                      2 4 2 nights min

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

                      Price per night from

                      $158

                      Price per night from

                      $158

                      Distance approx 15.29 km from Heritage Harbor

                      (3) Very Good 

                        19

                        BAY FRONT HOUSE WITH PRIVATE DOCK

                        Anna Maria Island / Bradenton Beach

                        Bradenton Beach house

                        2 6 2 nights min

                        • 2 bedrooms
                        • sleeps 6
                        • 2 nights min
                        • Nearest beach 0.1 mi
                        • Car not necessary
                        • Air conditioning

                        Price per night from

                        $200

                        Price per night from

                        $200

                        Distance approx 7.27 km from Heritage Harbor

                          12

                          2/2 Bradenton Condo available for 30+ day rentals $2000 monthly

                          Southwest Gulf Coast / Bradenton

                          Bradenton condo

                          2 6 30 nights min

                          • 2 bedrooms
                          • sleeps 6
                          • 30 nights min
                          • Child Friendly

                          Price per night from

                          $77

                          Price per night from

                          $77

                          Distance approx 15.3 km from Heritage Harbor

                            13

                            Holiday Beach Townhouses

                            Florida / Anna Maria Island

                            Anna Maria Island apartment

                            2 6 min stay varies

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

                            Price per night from

                            $251

                            Price per night from

                            $251

                            Distance approx 17.15 km from Heritage Harbor

                            (6) Very Good 

                              17

                              Starfish Unit at Sunset Beach Resort Beach Front Property

                              Southwest Gulf Coast / Sarasota

                              Sarasota apartment

                              1 4 min stay varies

                              • 1 bedroom
                              • sleeps 4
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Child Friendly
                              • Car not necessary

                              Price per night from

                              $285

                              Responds fast!
                              avg. 3 hours 16 minutes

                              Price per night from

                              $285

                              Distance approx 16.75 km from Heritage Harbor

                                15

                                Duplicate to NID 194265

                                Anna Maria Island / Holmes Beach

                                Holmes Beach house

                                5 10 7 nights min

                                • 5 bedrooms
                                • sleeps 10
                                • 7 nights min
                                • Swimming pool
                                • Car not necessary
                                • Air conditioning

                                Price per night from

                                $570

                                Price per night from

                                $570

                                Distance approx 14.46 km from Heritage Harbor

                                (2) Excellent 

                                  28

                                  Paradise Cottage: Steps to the Gulf of Mexico beach and Sarasota Bay!

                                  Florida / Longboat Key

                                  Longboat Key house

                                  3 7 7 nights min

                                  • 3 bedrooms
                                  • sleeps 7
                                  • 7 nights min
                                  • Nearest beach 0.25 mi
                                  • Child Friendly
                                  • Air conditioning

                                  Price per night from

                                  $228

                                  Price per night from

                                  $228

                                  Distance approx 4.66 km from Heritage Harbor

                                  (3) Excellent 

                                    16

                                    Lovely 3 BR Home with Office & Heated Pool at Tara

                                    Southwest Gulf Coast / Bradenton

                                    Bradenton house

                                    3 6 min stay varies

                                    • 3 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Nearest beach 20 mi
                                    • Swimming pool
                                    • Child Friendly

                                    Price per night from

                                    $143

                                    Price per night from

                                    $143

                                    Distance approx 17.21 km from Heritage Harbor

                                      30

                                      Beautiful Residence with Panoramic Sunrises

                                      Florida / Siesta Key

                                      Siesta Key condo

                                      2 5 14 nights min

                                      • 2 bedrooms
                                      • sleeps 5
                                      • 14 nights min
                                      • Beach / lakeside relaxation
                                      • Nearest beach 1 mi
                                      • Swimming pool

                                      Price per night from

                                      $130

                                      Price per night from

                                      $130

                                      Distance approx 16.58 km from Heritage Harbor

                                        34

                                        Mainsail Beach Inn - Townhouse 3 Bedroom Unit 11

                                        Anna Maria Island / Holmes Beach

                                        Holmes Beach hotel apartment

                                        3 8 min stay varies

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

                                        Price per night from

                                        $449

                                        Price per night from

                                        $449

                                        Distance approx 17.55 km from Heritage Harbor

                                        (2) Excellent 

                                          26

                                          Spacious 4bed air-con villa on Siesta Key

                                          Florida / Siesta Key

                                          Siesta Key villa

                                          4 8 min stay varies

                                          • 4 bedrooms
                                          • sleeps 8
                                          • min stay varies
                                          • Beach / lakeside relaxation
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $230

                                          Responds fast!
                                          avg. 56 minutes

                                          Price per night from

                                          $230

                                          Distance approx 0.1 km from Heritage Harbor

                                            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 11.44 km from Heritage Harbor

                                              12

                                              Barb's BaySide Retreat

                                              Florida / Palma Sola

                                              Palma Sola house

                                              3 6 3 nights min

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

                                              Price per night from

                                              $164

                                              Price per night from

                                              $164

                                              Distance approx 16.31 km from Heritage Harbor

                                              (31) Excellent 

                                              Certificate of Excellence

                                                38

                                                A Pearl of a Beach Home - with luxury private heated pool and hot tub

                                                Anna Maria Island / Holmes Beach

                                                Holmes Beach house

                                                3 6 7 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 7 nights min
                                                • Beach / lakeside relaxation
                                                • Nearest beach 0.4 mi
                                                • Swimming pool
                                                “out standing place to stay” I would/will stay here again when we come back down. Everything is top notch and the home has everything you need. We enjoyed the pool and hot tube, used it every night. Mike and Lesley are very easy to work with and do

                                                Certificate of Excellence

                                                Price per night from

                                                $244

                                                Responds fast!
                                                avg. 57 minutes

                                                Price per night from

                                                $244

                                                Distance approx 19.6 km from Heritage Harbor

                                                  24

                                                  Monthly Rental, 2 bed, 2 bath, Ocean view.

                                                  Southwest Gulf Coast / Sarasota

                                                  Sarasota condo

                                                  2 6 30 nights min

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

                                                  Price per night from

                                                  $114

                                                  Price per night from

                                                  $114

                                                  Distance approx 12.17 km from Heritage Harbor

                                                    13

                                                    The Majaec Inn Getaway with many Amenities Preview listing

                                                    Southwest Gulf Coast / Sarasota

                                                    Sarasota house

                                                    1 2 7 nights min

                                                    • 1 bedroom
                                                    • sleeps 2
                                                    • 7 nights min
                                                    • Child Friendly
                                                    • Air conditioning
                                                    • Private garden

                                                    Price per night from

                                                    $143

                                                    Price per night from

                                                    $143

                                                    Distance approx 13.87 km from Heritage Harbor

                                                      20

                                                      Awe-inspiring Views of Sarasota Bay

                                                      Florida / Longboat Key

                                                      Longboat Key condo

                                                      2 5 30 nights min

                                                      • 2 bedrooms
                                                      • sleeps 5
                                                      • 30 nights min
                                                      • Swimming pool
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $171

                                                      Price per night from

                                                      $171

                                                      Distance approx 17.28 km from Heritage Harbor

                                                        8

                                                        5 Minutes to Siesta Key Beach

                                                        Florida / Siesta Key

                                                        Siesta Key house

                                                        2 4 30 nights min

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

                                                        Price per night from

                                                        $244

                                                        Price per night from

                                                        $244

                                                        Distance approx 15.57 km from Heritage Harbor

                                                        (1) Very Good 

                                                          29

                                                          Private Beach,Waterfront/Gulf-Access Key West style 2b.1.5b.Town House U-3263

                                                          Florida / Ruskin

                                                          Ruskin townhouse

                                                          2 7 min stay varies

                                                          • 2 bedrooms
                                                          • sleeps 7
                                                          • min stay varies
                                                          • Beach / lakeside relaxation
                                                          • Nearest beach 1 mi
                                                          • Swimming pool

                                                          Price per night from

                                                          $159

                                                          Price per night from

                                                          $159

                                                          Distance approx 15.63 km from Heritage Harbor

                                                          (7) Very Good 

                                                            24

                                                            Private Beach Waterfront 2b.1.5b. Town House suite U-462, Tampa Bay

                                                            Florida / Ruskin

                                                            Ruskin townhouse

                                                            2 7 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 7
                                                            • min stay varies
                                                            • Beach / lakeside relaxation
                                                            • Nearest beach 1 mi
                                                            • Swimming pool

                                                            Price per night from

                                                            $159

                                                            Price per night from

                                                            $159

                                                            Distance approx 15.36 km from Heritage Harbor

                                                            (1) Excellent 

                                                              13

                                                              AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

                                                              Anna Maria Island / Bradenton Beach

                                                              Bradenton Beach apartment

                                                              2 5 14 nights min

                                                              • 2 bedrooms
                                                              • sleeps 5
                                                              • 14 nights min
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child Friendly

                                                              Price per night from

                                                              $171

                                                              Price per night from

                                                              $171

                                                              Distance approx 15.63 km from Heritage Harbor

                                                              (3) Very Good 

                                                                23

                                                                Waterfront,Gulf Access Luxury 2 bed /1.5 bath, Town House U-466 at Private Beach

                                                                Florida / Ruskin

                                                                Ruskin house

                                                                2 7 min stay varies

                                                                • 2 bedrooms
                                                                • sleeps 7
                                                                • min stay varies
                                                                • Beach / lakeside relaxation
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $159

                                                                Price per night from

                                                                $159

                                                                Distance approx 18.7 km from Heritage Harbor

                                                                  15

                                                                  Seasonal Amazing Luxury Waterfront Rental

                                                                  Florida / Apollo Beach

                                                                  Apollo Beach house

                                                                  6 11 90 nights min

                                                                  • 6 bedrooms
                                                                  • sleeps 11
                                                                  • 90 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $343

                                                                  Price per night from

                                                                  $343

                                                                  Distance approx 15.97 km from Heritage Harbor

                                                                  (5) Excellent 

                                                                    27

                                                                    Island Love Nest

                                                                    Anna Maria Island / Holmes Beach

                                                                    Holmes Beach apartment

                                                                    2 6 5 nights min

                                                                    • 2 bedrooms
                                                                    • sleeps 6
                                                                    • 5 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Nearest beach 0.3 mi
                                                                    • Child Friendly
                                                                    “Relaxing refuge” We had such a relaxing time during our stay. The condo is very clean and comfy with lots of little touches to make your stay even better. Its cozy enough for a couple but also has room for thr whole family. We enjoyed reading by the

                                                                    Price per night from

                                                                    $229

                                                                    Price per night from

                                                                    $229

                                                                    Distance approx 15.85 km from Heritage Harbor

                                                                    (3) Very Good 

                                                                      17

                                                                      Anna Maria Island #2 Beachside Palms

                                                                      Anna Maria Island / Holmes Beach

                                                                      Holmes Beach apartment

                                                                      2 6 7 nights min

                                                                      • 2 bedrooms
                                                                      • sleeps 6
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 0.1 mi
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $130

                                                                      Responds fast!
                                                                      avg. 3 hours 43 minutes

                                                                      Price per night from

                                                                      $130

                                                                      Distance approx 17.23 km from Heritage Harbor

                                                                      (7) Very Good 

                                                                        9

                                                                        Fabulous Condo in Front of Siesta Public Beach!

                                                                        Florida / Siesta Key

                                                                        Siesta Key apartment

                                                                        2 6 7 nights min

                                                                        • 2 bedrooms
                                                                        • sleeps 6
                                                                        • 7 nights min
                                                                        • Beach / lakeside relaxation
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        “3rd yr in a row.....” This was the 3rd yr we have stayed in this condo.. Dayal and Jaye make sure this condo is well stocked. The beds are super comfy and very clean... You literally only need to bring clothes and a toothbrush... Everything is there

                                                                        Price per night from

                                                                        $147

                                                                        Price per night from

                                                                        $147

                                                                        Distance approx 15.37 km from Heritage Harbor

                                                                          18

                                                                          runaway bay 2 bedroom condo with wonderful access to restaurant, beach, shopping

                                                                          Anna Maria Island / Holmes Beach

                                                                          Holmes Beach apartment

                                                                          2 6 30 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 30 nights min
                                                                          • Nearest beach 1 mi
                                                                          • Swimming pool
                                                                          • Car not necessary

                                                                          Price per night from

                                                                          $172

                                                                          Price per night from

                                                                          $172

                                                                          Distance approx 19.49 km from Heritage Harbor

                                                                          (1) Excellent 

                                                                            40

                                                                            Fisherman's Heaven

                                                                            Florida / Tampa

                                                                            Tampa house

                                                                            5 14 2 nights min

                                                                            • 5 bedrooms
                                                                            • sleeps 14
                                                                            • 2 nights min
                                                                            • Nearest beach 1 mi
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $570

                                                                            Price per night from

                                                                            $570

                                                                            Distance approx 16.07 km from Heritage Harbor

                                                                              17

                                                                              Westbay Point and Moorings 31- 2BD Condo with Waterfront Views of Bimini Bay

                                                                              Anna Maria Island / Holmes Beach

                                                                              Holmes Beach condo

                                                                              2 4 min stay varies

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • min stay varies
                                                                              • Swimming pool
                                                                              • Air conditioning
                                                                              • Private garden

                                                                              Price per night from

                                                                              $143

                                                                              Price per night from

                                                                              $143