Vacation Rentals with Pool in Montauk

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Filtering by: Swimming pool

95 vacation rentals

(7) Excellent 

    25

    Ocean Front Cottage Montauk for rent

    Hamptons / Montauk

    Montauk cottage

    2 6 min stay varies

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

    Price per night from

    $299

    Responds fast!
    avg. 2 hours 51 minutes

    Price per night from

    $299

      30

      Montauk Oceanfront Estate

      Hamptons / Montauk

      Montauk manor house

      5 10 7 nights min

      • 5 bedrooms
      • sleeps 10
      • 7 nights min
      • Beach / lakeside relaxation
      • Swimming pool
      • Child Friendly

      Price per night from

      $9,963

      Responds fast!
      avg. 2 hours 51 minutes

      Price per night from

      $9,963

        25

        6BR Montauk House w/Pool & Ocean Views!

        Hamptons / Montauk

        Montauk house

        6 13 min stay varies

        • 6 bedrooms
        • sleeps 13
        • min stay varies
        • Swimming pool
        • Child Friendly
        • Air conditioning

        Price per night from

        $2,061

        Responds fast!
        avg. 36 minutes

        Price per night from

        $2,061

          8

          Montauk Royal Atlantic Beach Resort

          Hamptons / Montauk

          Montauk condo

          1 4 2 nights min

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

          Price per night from

          $400

          Price per night from

          $400

            30

            Fully Renovated Beautiful Montauk Waterfront Condo

            Hamptons / Montauk

            Montauk condo

            2 5 4 nights min

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

            Price per night from

            $630

            Price per night from

            $630

            Great rentals within 20 miles that match your search

            Distance approx 11.92 km from Montauk

              11

              Newly Renovated in East Hampton

              Hamptons / East Hampton

              East Hampton house

              5 12 min stay varies

              • 5 bedrooms
              • sleeps 12
              • min stay varies
              • Swimming pool
              • Child Friendly
              • Private garden

              Price per night from

              $879

              Price per night from

              $879

              Distance approx 12.95 km from Montauk

              (1) Excellent 

                19

                Village Fringe glassy Modern with Pool and Tennis

                Hamptons / East Hampton

                East Hampton house

                3 6 min stay varies

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

                Price per night from

                $294

                Price per night from

                $294

                Distance approx 9.44 km from Montauk

                  23

                  Amagansett Estate 3 BR 60ft Pool

                  Hamptons / Amagansett

                  Amagansett house

                  3 6 3 nights min

                  • 3 bedrooms
                  • sleeps 6
                  • 3 nights min
                  • Nearest beach 8 mi
                  • Swimming pool
                  • Child Friendly

                  Price per night from

                  $1,027

                  Price per night from

                  $1,027

                  Distance approx 11.34 km from Montauk

                    29

                    Beautiful East Hampton Home w/ Hot Tub & Pool!

                    Hamptons / East Hampton

                    East Hampton house

                    4 8 min stay varies

                    • 4 bedrooms
                    • sleeps 8
                    • min stay varies
                    • Swimming pool
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $645

                    Responds fast!
                    avg. 36 minutes

                    Price per night from

                    $645

                    Distance approx 11.43 km from Montauk

                    (1) Excellent 

                      19

                      Serene & Private East Hampton Summer Rental w/pool

                      Hamptons / East Hampton

                      East Hampton house

                      2 4 7 nights min

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

                      Price per night from

                      $571

                      Price per night from

                      $571

                      Distance approx 19.17 km from Montauk

                        13

                        Perfect Hamptons Rental with Pool and Tennis

                        Hamptons / Bridgehampton

                        Bridgehampton house

                        4 8 7 nights min

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

                        Price per night from

                        $652

                        Responds fast!
                        avg. 32 minutes

                        Price per night from

                        $652

                        Distance approx 18.28 km from Montauk

                          15

                          ROMANTIC LUXURY RETREAT WITH POOL & WATER VIEWS, 1 MILE FROM SAG HARBOR VILLAGE

                          Hamptons / Sag Harbor

                          Sag Harbor house

                          3 6 3 nights min

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

                          Price per night from

                          $932

                          Price per night from

                          $932

                          Distance approx 9.44 km from Montauk

                            38

                            Amagansett Estate 5 Bedroom 60ft Pool

                            Hamptons / Amagansett

                            Amagansett villa

                            5 10 3 nights min

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

                            Price per night from

                            $1,369

                            Price per night from

                            $1,369

                            Distance approx 9.19 km from Montauk

                              26

                              CHIC RETREAT!! Walk to Desirable Bay BEACH!!

                              Hamptons / East Hampton

                              East Hampton house

                              3 6 1 night min

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

                              Price per night from

                              $2,510

                              Responds fast!
                              avg. 18 minutes

                              Price per night from

                              $2,510

                              Distance approx 9.69 km from Montauk

                                24

                                Amagansett Estate 4BR 60ft Pool

                                Hamptons / Amagansett

                                Amagansett manor house

                                4 8 3 nights min

                                • 4 bedrooms
                                • sleeps 8
                                • 3 nights min
                                • Beach / lakeside relaxation
                                • Swimming pool
                                • Child Friendly

                                Price per night from

                                $1,231

                                Price per night from

                                $1,231

                                Distance approx 11.19 km from Montauk

                                  28

                                  Private Beach Getaway

                                  Hamptons / Springs

                                  Springs house

                                  3 6 5 nights min

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

                                  Price per night from

                                  $469

                                  Responds fast!
                                  avg. 3 hours 41 minutes

                                  Price per night from

                                  $469

                                  Distance approx 15.41 km from Montauk

                                  (1) Excellent 

                                    16

                                    East Hampton/ Sag Harbor, 8 Acres, Pool, Tennis Ct, Hot tub, Sauna

                                    Hamptons / East Hampton

                                    East Hampton house

                                    5 8 7 nights min

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

                                    Price per night from

                                    $1,353

                                    Responds fast!
                                    avg. 3 hours 39 minutes

                                    Price per night from

                                    $1,353

                                    Distance approx 19.17 km from Montauk

                                      18

                                      Ideal Bridgehamtpon Getway with Pool & Tennis

                                      Hamptons / Bridgehampton

                                      Bridgehampton house

                                      4 8 7 nights min

                                      • 4 bedrooms
                                      • sleeps 8
                                      • 7 nights min
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $856

                                      Responds fast!
                                      avg. 1 hour 54 minutes

                                      Price per night from

                                      $856

                                      Distance approx 12.93 km from Montauk

                                        7

                                        Spectacular 5 Bedroom Contemporary Getaway..Private Oasis........Newly Renovated

                                        Hamptons / East Hampton

                                        East Hampton house

                                        5 10 3 nights min

                                        • 5 bedrooms
                                        • sleeps 10
                                        • 3 nights min
                                        • Beach / lakeside relaxation
                                        • Swimming pool
                                        • Child Friendly

                                        Price per night from

                                        $1,826

                                        Responds fast!
                                        avg. 2 hours 54 minutes

                                        Price per night from

                                        $1,826

                                        Distance approx 17.46 km from Montauk

                                        (1) Excellent 

                                          19

                                          Sag Harbor Village Fringe, Great Location

                                          Hamptons / Sag Harbor

                                          Sag Harbor house

                                          4 8 6 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 6 nights min
                                          • Nearest beach 3 mi
                                          • Swimming pool
                                          • Child Friendly

                                          Price per night from

                                          $2,282

                                          Responds fast!
                                          avg. 3 hours 39 minutes

                                          Price per night from

                                          $2,282

                                          Distance approx 12.6 km from Montauk

                                            20

                                            Bright, White 4 Bed Contemporary in NW Woods on 2 Acres!

                                            Hamptons / East Hampton

                                            East Hampton house

                                            4 8 min stay varies

                                            • 4 bedrooms
                                            • sleeps 8
                                            • min stay varies
                                            • Swimming pool
                                            • Ask about children
                                            • Air conditioning

                                            Price per night from

                                            $461

                                            Price per night from

                                            $461

                                            Distance approx 13.28 km from Montauk

                                            (4) Excellent 

                                              23

                                              Beautiful East Hampton Home / Heated Pool / Luxury Sheets and Towels

                                              Hamptons / East Hampton

                                              East Hampton house

                                              4 10 3 nights min

                                              • 4 bedrooms
                                              • sleeps 10
                                              • 3 nights min
                                              • Beach / lakeside relaxation
                                              • Nearest beach 0.16 mi
                                              • Swimming pool

                                              Price per night from

                                              $1,712

                                              Responds fast!
                                              avg. 2 hours 11 minutes

                                              Price per night from

                                              $1,712

                                              Distance approx 10.32 km from Montauk

                                              (5) Excellent 

                                                41

                                                East Hampton Family Retreat with Cottage

                                                Hamptons / East Hampton

                                                East Hampton house

                                                5 12 min stay varies

                                                • 5 bedrooms
                                                • sleeps 12
                                                • min stay varies
                                                • Beach / lakeside relaxation
                                                • Nearest beach 5 mi
                                                • Swimming pool
                                                “Great House, Great Host” My friends and I spent a great weekend at this house and were blown away by house nice the house was and how gracious Leanna was as a host. We made good use of the pool (played several house of pool volleyball) and the hot tu
                                                …see more

                                                Price per night from

                                                $704

                                                Price per night from

                                                $704

                                                Distance approx 11.96 km from Montauk

                                                  18

                                                  Waterview renovated 5 bedroom house with pool

                                                  Hamptons / East Hampton

                                                  East Hampton house

                                                  5 12 7 nights min

                                                  • 5 bedrooms
                                                  • sleeps 12
                                                  • 7 nights min
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $1,141

                                                  Price per night from

                                                  $1,141

                                                  Distance approx 19.54 km from Montauk

                                                  (1) Excellent 

                                                    26

                                                    Bridgehampton Village Beauty

                                                    Hamptons / Bridgehampton

                                                    Bridgehampton house

                                                    6 12 3 nights min

                                                    • 6 bedrooms
                                                    • sleeps 12
                                                    • 3 nights min
                                                    • Swimming pool
                                                    • Child Friendly
                                                    • Air conditioning

                                                    Price per night from

                                                    $1,426

                                                    Responds fast!
                                                    avg. 2 hours 5 minutes

                                                    Price per night from

                                                    $1,426

                                                    Distance approx 13.14 km from Montauk

                                                      27

                                                      Comfort and quality w Pool,Tennis, Home Theater, Sonos Music System

                                                      Hamptons / East Hampton

                                                      East Hampton house

                                                      3 6 14 nights min

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

                                                      Price per night from

                                                      $457

                                                      Responds fast!
                                                      avg. 3 hours 25 minutes

                                                      Price per night from

                                                      $457

                                                      Distance approx 11.77 km from Montauk

                                                        17

                                                        RENOVATED BEACH HOUSE W/ HEATED POOL & FIREPLACE!

                                                        Hamptons / East Hampton

                                                        East Hampton house

                                                        4 9 min stay varies

                                                        • 4 bedrooms
                                                        • sleeps 9
                                                        • min stay varies
                                                        • Beach / lakeside relaxation
                                                        • Swimming pool
                                                        • Child Friendly

                                                        Price per night from

                                                        $645

                                                        Price per night from

                                                        $645

                                                        Distance approx 9.39 km from Montauk

                                                          16

                                                          Amagansett Summer Rental - Charming renovated Farmhouse with pool

                                                          Hamptons / Amagansett

                                                          Amagansett house

                                                          3 7 14 nights min

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

                                                          Price per night from

                                                          $1,011

                                                          Price per night from

                                                          $1,011

                                                          Distance approx 12.98 km from Montauk

                                                            23

                                                            East Hampton Village Classic , South of Highway

                                                            Hamptons / East Hampton

                                                            East Hampton house

                                                            7 12 14 nights min

                                                            • 7 bedrooms
                                                            • sleeps 12
                                                            • 14 nights min
                                                            • Nearest beach 2 mi
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $3,349

                                                            Responds fast!
                                                            avg. 3 hours 14 minutes

                                                            Price per night from

                                                            $3,349

                                                            Distance approx 17.65 km from Montauk

                                                              18

                                                              Sag Harbor European Designer's Home

                                                              Hamptons / Sag Harbor

                                                              Sag Harbor house

                                                              4 8 30 nights min

                                                              • 4 bedrooms
                                                              • sleeps 8
                                                              • 30 nights min
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Car not necessary

                                                              Price per night from

                                                              $1,902

                                                              Price per night from

                                                              $1,902

                                                              Distance approx 10.17 km from Montauk

                                                                24

                                                                Breathtaking Hamptons Hideaway

                                                                Hamptons / Springs

                                                                Springs house

                                                                6 14 7 nights min

                                                                • 6 bedrooms
                                                                • sleeps 14
                                                                • 7 nights min
                                                                • Swimming pool
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $2,512

                                                                Price per night from

                                                                $2,512

                                                                Distance approx 11.79 km from Montauk

                                                                  13

                                                                  East Hampton Charming Cottage South Of the Highway Near Ocean/ Further Lane

                                                                  Hamptons / East Hampton

                                                                  East Hampton house

                                                                  3 8 14 nights min

                                                                  • 3 bedrooms
                                                                  • sleeps 8
                                                                  • 14 nights min
                                                                  • Swimming pool
                                                                  • Child Friendly
                                                                  • Air conditioning

                                                                  Price per night from

                                                                  $1,417

                                                                  Price per night from

                                                                  $1,417

                                                                  Distance approx 12.34 km from Montauk

                                                                    15

                                                                    East Hampton Village Luxury Rental

                                                                    Hamptons / East Hampton

                                                                    East Hampton house

                                                                    5 12 14 nights min

                                                                    • 5 bedrooms
                                                                    • sleeps 12
                                                                    • 14 nights min
                                                                    • Beach / lakeside relaxation
                                                                    • Swimming pool
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $4,074

                                                                    Price per night from

                                                                    $4,074

                                                                    Distance approx 11.37 km from Montauk

                                                                      6

                                                                      Family Vacation Home, heated pool

                                                                      Hamptons / Amagansett

                                                                      Amagansett house

                                                                      3 6 3 nights min

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

                                                                      Price per night from

                                                                      $685

                                                                      Price per night from

                                                                      $685

                                                                      Distance approx 16.68 km from Montauk

                                                                        19

                                                                        in town of east hampton, bike to beach

                                                                        Hamptons / Wainscott

                                                                        Wainscott house

                                                                        4 10 min stay varies

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

                                                                        Price per night from

                                                                        $411

                                                                        Price per night from

                                                                        $411

                                                                        Distance approx 13.98 km from Montauk

                                                                        (2) Excellent 

                                                                          22

                                                                          East Hampton Classic

                                                                          Hamptons / East Hampton

                                                                          East Hampton house

                                                                          4 10 min stay varies

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

                                                                          Price per night from

                                                                          $514

                                                                          Responds fast!
                                                                          avg. 2 hours 27 minutes

                                                                          Price per night from

                                                                          $514

                                                                          Distance approx 10.9 km from Montauk

                                                                            13

                                                                            Lushly Landscaped Contemporary With Pool East Hampton North

                                                                            Hamptons / East Hampton

                                                                            East Hampton house

                                                                            4 8 min stay varies

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • min stay varies
                                                                            • Nearest beach 1 mi
                                                                            • Swimming pool
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $586

                                                                            Price per night from

                                                                            $586

                                                                            Distance approx 13.17 km from Montauk

                                                                              27

                                                                              Loft in a SaltBox

                                                                              Hamptons / East Hampton

                                                                              East Hampton house

                                                                              4 7 14 nights min

                                                                              • 4 bedrooms
                                                                              • sleeps 7
                                                                              • 14 nights min
                                                                              • Swimming pool
                                                                              • Ask about children
                                                                              • Air conditioning

                                                                              Price per night from

                                                                              $864

                                                                              Price per night from

                                                                              $864