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94 Houses

Great rentals within 20 miles that match your search

Distance approx 5.71 km from Middle Island Show on Map

    42

    Upscale Beach House Near Vineyards & Farm Stands, 1.5 hrs to NYC The Dunes

    Long Island / Rocky Point

    Rocky Point house

    2 4 min stay varies

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

    Price per night from

    $415

    Responds fast!
    avg. 2 hours 29 minutes

    Price per night from

    $415

    Distance approx 7.06 km from Middle Island Show on Map

      50

      Beach House On The Sand 1m Vineyards Farms 1.5hr NYC The Degan

      Long Island / Wading River

      Wading River house

      4 10 min stay varies

      • 4 bedrooms
      • sleeps 10
      • min stay varies
      • Child Friendly
      • Air conditioning
      • Pet Friendly

      Price per night from

      $725

      Responds fast!
      avg. 2 hours 29 minutes

      Price per night from

      $725

      Distance approx 10.4 km from Middle Island

        21

        Perfect summer haven, ten minutes walk to village

        Long Island / Bellport

        Bellport house

        3 10 4 nights min

        • 3 bedrooms
        • sleeps 10
        • 4 nights min
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $687

        Price per night from

        $687

        Distance approx 5.47 km from Middle Island Show on Map

          25

          Rocky Point Home w/ 2 Decks Overlooking the Water!

          Long Island / Rocky Point

          Rocky Point house

          3 8 min stay varies

          • 3 bedrooms
          • sleeps 8
          • min stay varies
          • Child Friendly
          • Air conditioning

          Price per night from

          $315

          Responds fast!
          avg. 7 minutes

          Price per night from

          $315

          Distance approx 13.37 km from Middle Island

            11

            Country Life in Westhampton

            Hamptons / Westhampton

            Westhampton house

            3 8 3 nights min

            • 3 bedrooms
            • sleeps 8
            • 3 nights min
            • Child Friendly
            • Air conditioning

            Price per night from

            $515

            Price per night from

            $515

            Distance approx 15.45 km from Middle Island

            (3) Excellent 

              24

              Waterfront Hamptons Beach House w/ Dock, Hot Tub, & Awesome Views, Walk to Beach

              Hamptons / Westhampton Beach

              Westhampton Beach house

              3 6 min stay varies

              • 3 bedrooms
              • sleeps 6
              • min stay varies
              • Beach / lakeside relaxation
              • Nearest beach 0 mi
              • Child Friendly

              Price per night from

              $205

              Price per night from

              $205

              Distance approx 7.03 km from Middle Island Show on Map

              (1) Excellent 

                44

                Large Luxury Beach House AMAZING VIEWS-North Fork Hamptons

                Long Island / Wading River

                Wading River house

                4 12 min stay varies

                • 4 bedrooms
                • sleeps 12
                • min stay varies
                • Child Friendly
                • Air conditioning
                • Pet Friendly

                Price per night from

                $829

                Responds fast!
                avg. 2 hours 29 minutes

                Price per night from

                $829

                Distance approx 9.35 km from Middle Island

                  27

                  "Above the Bay" - Suite-Bedrm ,Den,Bath & Kitchen

                  Long Island / East Patchogue

                  East Patchogue apartment

                  1 2 3 nights min

                  • 1 bedroom
                  • sleeps 2
                  • 3 nights min
                  • Air conditioning
                  • Private garden

                  Price per night from

                  $166

                  Price per night from

                  $166

                  Distance approx 19.1 km from Middle Island

                    24

                    NEW! Cozy Fire Island Studio - Steps to the Beach!

                    Fire Island / Ocean Beach

                    Ocean Beach studio

                    Studio 2 min stay varies

                    • Studio
                    • sleeps 2
                    • min stay varies
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $132

                    Responds fast!
                    avg. 19 minutes

                    Price per night from

                    $132

                    Distance approx 19.85 km from Middle Island

                      19

                      Charming Bay View Cottage

                      Fire Island / Ocean Beach

                      Ocean Beach cottage

                      2 5 min stay varies

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

                      Price per night from

                      $458

                      Price per night from

                      $458

                      Distance approx 7.01 km from Middle Island Show on Map

                      (2) Excellent 

                        55

                        Private Romantic Rustic Beach House--Vineyards, Farms--Sleeps 5 (The Joyce)

                        Long Island / Wading River

                        Wading River cottage

                        1 5 min stay varies

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

                        Price per night from

                        $312

                        Responds fast!
                        avg. 2 hours 29 minutes

                        Price per night from

                        $312

                        Distance approx 7.08 km from Middle Island Show on Map

                        (1) Excellent 

                          36

                          True beach House On The Beach! Golf, Bike, Shop Once Upon A Tide

                          Long Island / Wading River

                          Wading River house

                          4 11 min stay varies

                          • 4 bedrooms
                          • sleeps 11
                          • min stay varies
                          • Child Friendly
                          • Air conditioning
                          • Pet Friendly

                          Price per night from

                          $725

                          Responds fast!
                          avg. 2 hours 29 minutes

                          Price per night from

                          $725

                          Distance approx 13.25 km from Middle Island

                          (3) Very Good 

                            21

                            3BR/2BA- Private Heated Pool Steps to Moriches Bay

                            Hamptons / Remsenburg

                            Remsenburg house

                            3 6 min stay varies

                            • 3 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Beach / lakeside relaxation
                            • Swimming pool
                            • Child Friendly

                            Price per night from

                            $84

                            Price per night from

                            $84

                            Distance approx 13.66 km from Middle Island

                            (2) Excellent 

                              45

                              8 BR Luxury Oceanfront house pool+Jacuzzi On Ocean,Call For Last Minute Deals!

                              Hamptons / Westhampton Beach

                              Westhampton Beach house

                              8 18 min stay varies

                              • 8 bedrooms
                              • sleeps 18
                              • min stay varies
                              • Beach / lakeside relaxation
                              • Swimming pool
                              • Child Friendly

                              Price per night from

                              $1,750

                              Price per night from

                              $1,750

                              Distance approx 7.24 km from Middle Island Show on Map

                              (6) Excellent 

                                46

                                Luxury Beach House w Panoramic Views- 1.5hrs to NYC Sleeps 10 Soundview

                                Long Island / Wading River

                                Wading River house

                                3 10 min stay varies

                                • 3 bedrooms
                                • sleeps 10
                                • min stay varies
                                • Child Friendly
                                • Air conditioning
                                • Pet Friendly

                                Price per night from

                                $518

                                Responds fast!
                                avg. 2 hours 29 minutes

                                Price per night from

                                $518

                                Distance approx 7.4 km from Middle Island Show on Map

                                  27

                                  Beach Cottage Water Views private Steps to the Beach

                                  Long Island / Wading River

                                  Wading River house

                                  4 2 min stay varies

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

                                  Price per night from

                                  $235

                                  Responds fast!
                                  avg. 2 hours 29 minutes

                                  Price per night from

                                  $235

                                  Distance approx 6.5 km from Middle Island Show on Map

                                    51

                                    Frank Lloyd Wright Prairie Style Home on 4 Acres Wild Life Refuge

                                    Long Island / Brookhaven

                                    Brookhaven house

                                    5 15 3 nights min

                                    • 5 bedrooms
                                    • sleeps 15
                                    • 3 nights min
                                    • Child Friendly
                                    • Air conditioning
                                    • Pet Friendly

                                    Price per night from

                                    $567

                                    Responds fast!
                                    avg. 1 hour 24 minutes

                                    Price per night from

                                    $567

                                    Distance approx 13.19 km from Middle Island

                                      6

                                      Lovely Hampton Estate

                                      Hamptons / Remsenburg

                                      Remsenburg villa

                                      5 9 5 nights min

                                      • 5 bedrooms
                                      • sleeps 9
                                      • 5 nights min
                                      • Child Friendly
                                      • Ask about pets

                                      Price per night from

                                      $1,489

                                      Responds fast!
                                      avg. 40 minutes

                                      Price per night from

                                      $1,489

                                      Distance approx 17.11 km from Middle Island

                                      (5) Excellent 

                                        22

                                        "Amazing Summer Getaway In East Quogue"

                                        Hamptons / East Quogue

                                        East Quogue house

                                        8 8 2 nights min

                                        • 8 bedrooms
                                        • sleeps 8
                                        • 2 nights min
                                        • Child Friendly

                                        Price per night from

                                        $1,374

                                        Price per night from

                                        $1,374

                                        Distance approx 19.34 km from Middle Island

                                          13

                                          Oceanfront Luxury Retreat

                                          Fire Island / Ocean Bay Park

                                          Ocean Bay Park house

                                          5 12 3 nights min

                                          • 5 bedrooms
                                          • sleeps 12
                                          • 3 nights min
                                          • Child Friendly

                                          Price per night from

                                          $2,290

                                          Price per night from

                                          $2,290

                                          Distance approx 7.29 km from Middle Island Show on Map

                                            38

                                            New Beach House North Fork Vineyards 1 Mile Farms Hamptons (seaside)

                                            Long Island / Wading River

                                            Wading River house

                                            4 10 min stay varies

                                            • 4 bedrooms
                                            • sleeps 10
                                            • min stay varies
                                            • Child Friendly
                                            • Air conditioning
                                            • Pet Friendly

                                            Price per night from

                                            $138

                                            Responds fast!
                                            avg. 2 hours 29 minutes

                                            Price per night from

                                            $138

                                            Distance approx 17.49 km from Middle Island

                                            (3) Very Good 

                                              30

                                              Luxury Hamptons Quogue Village 4BR Modernist Retre

                                              Hamptons / Quogue

                                              Quogue house

                                              4 8 14 nights min

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

                                              Price per night from

                                              $687

                                              Price per night from

                                              $687

                                              Distance approx 11.62 km from Middle Island

                                                6

                                                Waterview House Perfect for Large Families

                                                Long Island / East Moriches

                                                East Moriches house

                                                4 12 min stay varies

                                                • 4 bedrooms
                                                • sleeps 12
                                                • min stay varies
                                                • Child Friendly
                                                • Air conditioning
                                                • Private garden

                                                Price per night from

                                                $835

                                                Price per night from

                                                $835

                                                Distance approx 19.24 km from Middle Island

                                                (2) Very Good 

                                                  9

                                                  Romantic Luxury Winery Apartment

                                                  North Fork / Jamesport

                                                  Jamesport apartment

                                                  1 2 2 nights min

                                                  • 1 bedroom
                                                  • sleeps 2
                                                  • 2 nights min
                                                  • Nearest beach 2 mi
                                                  • Car not necessary
                                                  • Air conditioning

                                                  Price per night from

                                                  $287

                                                  Price per night from

                                                  $287

                                                  Distance approx 11.88 km from Middle Island

                                                    12

                                                    Beautiful Waterfront Home with private beach

                                                    Long Island / East Setauket

                                                    East Setauket house

                                                    5 10 21 nights min

                                                    • 5 bedrooms
                                                    • sleeps 10
                                                    • 21 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 2 mi
                                                    • Child Friendly

                                                    Price per night from

                                                    $1,129

                                                    Price per night from

                                                    $1,129

                                                    Distance approx 2.53 km from Middle Island Show on Map

                                                    (1) Excellent 

                                                      9

                                                      Central Location to Long Island Attractions

                                                      Long Island / Coram

                                                      Coram house

                                                      2 4 4 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 4 nights min
                                                      • Air conditioning
                                                      • Private garden

                                                      Price per night from

                                                      $144

                                                      Price per night from

                                                      $144

                                                      Distance approx 7.36 km from Middle Island Show on Map

                                                        49

                                                        Luxury Beach House near Hamptons Vineyards walk to Restaurant 60 miles NYC

                                                        Long Island / Wading River

                                                        Wading River house

                                                        4 10 min stay varies

                                                        • 4 bedrooms
                                                        • sleeps 10
                                                        • min stay varies
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Pet Friendly

                                                        Price per night from

                                                        $773

                                                        Responds fast!
                                                        avg. 2 hours 29 minutes

                                                        Price per night from

                                                        $773

                                                        Distance approx 13.47 km from Middle Island

                                                          34

                                                          Waterfront Westhampton House w/Private Pool & Dock

                                                          Hamptons / Westhampton Beach

                                                          Westhampton Beach house

                                                          5 10 min stay varies

                                                          • 5 bedrooms
                                                          • sleeps 10
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $1,145

                                                          Responds fast!
                                                          avg. 19 minutes

                                                          Price per night from

                                                          $1,145

                                                          Distance approx 7.34 km from Middle Island Show on Map

                                                          (1) Excellent 

                                                            41

                                                            Luxury Beach Cottage Wineries, Shopping & the Hamptons Low Monthly Rates

                                                            Long Island / Wading River

                                                            Wading River cottage

                                                            1 4 min stay varies

                                                            • 1 bedroom
                                                            • sleeps 4
                                                            • min stay varies
                                                            • Child Friendly
                                                            • Air conditioning
                                                            • Pet Friendly

                                                            Price per night from

                                                            $62

                                                            Responds fast!
                                                            avg. 2 hours 29 minutes

                                                            Price per night from

                                                            $62

                                                            Distance approx 17.27 km from Middle Island

                                                            (1) Excellent 

                                                              23

                                                              Cherry Grove Oceanfront with Heated Pool

                                                              Fire Island / Cherry Grove

                                                              Cherry Grove house

                                                              1 4 7 nights min

                                                              • 1 bedroom
                                                              • sleeps 4
                                                              • 7 nights min
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Car not necessary

                                                              Price per night from

                                                              $573

                                                              Price per night from

                                                              $573

                                                              Distance approx 17.16 km from Middle Island

                                                              (4) Excellent 

                                                                45

                                                                5 bedroom Private Family Get Away

                                                                Hamptons / Westhampton Beach

                                                                Westhampton Beach house

                                                                5 10 2 nights min

                                                                • 5 bedrooms
                                                                • sleeps 10
                                                                • 2 nights min
                                                                • Nearest beach 5 mi
                                                                • Swimming pool
                                                                • Child Friendly

                                                                Price per night from

                                                                $401

                                                                Responds fast!
                                                                avg. 2 hours 48 minutes

                                                                Price per night from

                                                                $401

                                                                Distance approx 19.85 km from Middle Island

                                                                (3) Average 

                                                                  33

                                                                  Blue Parrot 3 Bedroom, 1 bath, large deck, wi-fi, sat TV, d/w, microwave

                                                                  Fire Island / Ocean Beach

                                                                  Ocean Beach apartment

                                                                  3 8 3 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 3 nights min
                                                                  • Nearest beach 0.2 mi
                                                                  • Child Friendly
                                                                  • Car not necessary

                                                                  Price per night from

                                                                  $344

                                                                  Responds fast!
                                                                  avg. 1 hour 16 minutes

                                                                  Price per night from

                                                                  $344

                                                                  Distance approx 17.18 km from Middle Island

                                                                    11

                                                                    Beautiful and sunny hamptons home with pool

                                                                    Hamptons / East Hampton

                                                                    East Hampton house

                                                                    4 6 7 nights min

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

                                                                    Price per night from

                                                                    $1,145

                                                                    Price per night from

                                                                    $1,145

                                                                    Distance approx 16.24 km from Middle Island

                                                                      4

                                                                      Hello

                                                                      Hamptons / Westhampton Beach

                                                                      Westhampton Beach house

                                                                      5 1 2 nights min

                                                                      • 5 bedrooms
                                                                      • sleeps 1
                                                                      • 2 nights min
                                                                      • Child Friendly
                                                                      • Car not necessary
                                                                      • Air conditioning

                                                                      Price per night from

                                                                      $22,901

                                                                      Price per night from

                                                                      $22,901

                                                                      Distance approx 14.94 km from Middle Island

                                                                        8

                                                                        Westhampton SeaBreeze Suite

                                                                        Hamptons / Westhampton

                                                                        Westhampton hotel apartment

                                                                        1 4 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 1 night min
                                                                        • Beach / lakeside relaxation
                                                                        • Nearest beach 10 mi
                                                                        • Child Friendly

                                                                        Price per night from

                                                                        $172

                                                                        Responds fast!
                                                                        avg. 2 hours 48 minutes

                                                                        Price per night from

                                                                        $172

                                                                        Distance approx 19.33 km from Middle Island

                                                                        (1) Excellent 

                                                                          29

                                                                          Cozy Ranch

                                                                          Hamptons / East Quogue

                                                                          East Quogue apartment

                                                                          2 6 min stay varies

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • min stay varies
                                                                          • Nearest beach 7 mi
                                                                          • Child Friendly
                                                                          • Pet Friendly

                                                                          Price per night from

                                                                          $189

                                                                          Responds fast!
                                                                          avg. 1 hour 56 minutes

                                                                          Price per night from

                                                                          $189

                                                                          Distance approx 11.35 km from Middle Island

                                                                          (1) Excellent 

                                                                            38

                                                                            East End Retreat - Steps to the beach! - Northfork - Monthly Rentals Available!

                                                                            Long Island / Baiting Hollow

                                                                            Baiting Hollow house

                                                                            4 8 min stay varies

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • min stay varies
                                                                            • Beach / lakeside relaxation
                                                                            • Child Friendly
                                                                            • Air conditioning

                                                                            Price per night from

                                                                            $343

                                                                            Responds fast!
                                                                            avg. 3 hours 3 minutes

                                                                            Price per night from

                                                                            $343

                                                                            Distance approx 13.68 km from Middle Island

                                                                              29

                                                                              Westhampton Dunes Home w/Ocean View & Beach Access

                                                                              Hamptons / Remsenburg

                                                                              Remsenburg house

                                                                              4 10 min stay varies

                                                                              • 4 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $705

                                                                              Responds fast!
                                                                              avg. 19 minutes

                                                                              Price per night from

                                                                              $705