Vacation Rentals with Pool in Long Island

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

Filtering by: Swimming pool

187 vacation rentals
    78

    Sagaponack Compound

    Hamptons / Sagaponack

    Sagaponack house

    7 20 min stay varies

    • 7 bedrooms
    • sleeps 20
    • min stay varies
    • Swimming pool
    • Child Friendly
    • Car not necessary

    Price per night from

    $1,374

    Price per night from

    $1,374

      28

      Hampton Estate Villa Monthly Rental

      Hamptons / Water Mill

      Water Mill house

      6 12 30 nights min

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

      Price per night from

      $954

      Price per night from

      $954

      (1) Excellent 

        6

        July - August 2017. Open floor plan, modernist house in the Village of Springs

        Hamptons / East Hampton

        East Hampton house

        2 4 min stay varies

        • 2 bedrooms
        • sleeps 4
        • min stay varies
        • Nearest beach 4 mi
        • Swimming pool
        • Air conditioning

        Price per night from

        $287

        Price per night from

        $287

        (11) Excellent 

        Certificate of Excellence

          14

          Waterfront Condo C204 at The Cliffside Resort

          North Fork / Greenport

          Greenport apartment

          2 6 min stay varies

          • 2 bedrooms
          • sleeps 6
          • min stay varies
          • Beach / lakeside relaxation
          • Nearest beach 0 mi
          • Swimming pool

          Certificate of Excellence

          Price per night from

          $287

          Responds fast!
          avg. 3 hours 42 minutes

          Price per night from

          $287

          (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

              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

              $859

              Price per night from

              $859

              (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

                (1) Excellent 

                  28

                  Southampton Waterfront- Beach Home- 2 kayaks!

                  Hamptons / Southampton

                  Southampton house

                  5 10 min stay varies

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

                  Price per night from

                  $1,947

                  Responds fast!
                  avg. 1 hour 45 minutes

                  Price per night from

                  $1,947

                    28

                    Sag Harbor Home w/ Pool - 5 Mins to Downtown!

                    Hamptons / Sag Harbor

                    Sag Harbor house

                    4 8 min stay varies

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

                    Price per night from

                    $602

                    Responds fast!
                    avg. 8 minutes

                    Price per night from

                    $602

                      20

                      Luxury House w Pool 6 acres HAMPTONS!

                      Hamptons / Wainscott

                      Wainscott house

                      4 8 21 nights min

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

                      Price per night from

                      $2,061

                      Responds fast!
                      avg. 1 hour 48 minutes

                      Price per night from

                      $2,061

                        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

                        $647

                        Responds fast!
                        avg. 8 minutes

                        Price per night from

                        $647

                          28

                          4BR Southampton House w/Private Pool & Garden

                          Hamptons / Southampton

                          Southampton house

                          4 7 7 nights min

                          • 4 bedrooms
                          • sleeps 7
                          • 7 nights min
                          • Swimming pool
                          • Suitable for children age 5+
                          • Air conditioning

                          Price per night from

                          $973

                          Responds fast!
                          avg. 8 minutes

                          Price per night from

                          $973

                            27

                            Beautiful Hampton Bays Vacation Rental Home

                            Southampton / Hampton Bays

                            Hampton Bays house

                            3 12 3 nights min

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

                            Price per night from

                            $695

                            Price per night from

                            $695

                            (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

                              $573

                              Price per night from

                              $573

                                14

                                Waterfront Paradise for boaters & family reunions!

                                Southampton / Hampton Bays

                                Hampton Bays house

                                6 12 14 nights min

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

                                Price per night from

                                $1,145

                                Price per night from

                                $1,145

                                  11

                                  Amagansett House with Pool near Village & Beach

                                  Hamptons / Amagansett

                                  Amagansett house

                                  4 8 21 nights min

                                  • 4 bedrooms
                                  • sleeps 8
                                  • 21 nights min
                                  • Beach / lakeside relaxation
                                  • Swimming pool
                                  • Air conditioning

                                  Price per night from

                                  $1,309

                                  Price per night from

                                  $1,309

                                    11

                                    Hamptons Summer Rental - East Quogue

                                    Hamptons / East Quogue

                                    East Quogue house

                                    4 10 6 nights min

                                    • 4 bedrooms
                                    • sleeps 10
                                    • 6 nights min
                                    • Beach / lakeside relaxation
                                    • Swimming pool
                                    • Child Friendly

                                    Price per night from

                                    $573

                                    Price per night from

                                    $573

                                      46

                                      Large swimming pool/Walking distance to the bay

                                      Southampton / Hampton Bays

                                      Hampton Bays house

                                      4 10 14 nights min

                                      • 4 bedrooms
                                      • sleeps 10
                                      • 14 nights min
                                      • Swimming pool
                                      • Ask about children
                                      • Car not necessary

                                      Price per night from

                                      $785

                                      Price per night from

                                      $785

                                      (5) Excellent 

                                        15

                                        Beech Tree Cottage

                                        Hamptons / Sag Harbor

                                        Sag Harbor cottage

                                        2 4 2 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 2 nights min
                                        • Beach / lakeside relaxation
                                        • Nearest beach 3 mi
                                        • Swimming pool
                                        “Loved this place” This is the perfect little getaway for those who wish to avoid the pretentiousness of East Hampton and Southampton and still enjoy everything that the Hamptons has to offer. Best things - very cute little cottage. Good enough spa
                                        …see more

                                        Price per night from

                                        $573

                                        Price per night from

                                        $573

                                          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

                                          (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

                                            $295

                                            Price per night from

                                            $295

                                              13

                                              The Perfect Getaway! #1

                                              Long Island / Great Neck

                                              Great Neck house

                                              3 2 2 nights min

                                              • 3 bedrooms
                                              • sleeps 2
                                              • 2 nights min
                                              • Swimming pool
                                              • Child Friendly
                                              • Private garden

                                              Price per night from

                                              $144

                                              Price per night from

                                              $144

                                                26

                                                Glen Cove Home w/ Heated Pool, Hot Tub & Backyard!

                                                Long Island / Glen Cove

                                                Glen Cove house

                                                3 7 min stay varies

                                                • 3 bedrooms
                                                • sleeps 7
                                                • min stay varies
                                                • Swimming pool
                                                • Child Friendly
                                                • Air conditioning

                                                Price per night from

                                                $298

                                                Responds fast!
                                                avg. 8 minutes

                                                Price per night from

                                                $298

                                                  24

                                                  Romantic Shelter Island Cottage w/2 Pools & a Pond

                                                  Shelter Island / Shelter Island Heights

                                                  Shelter Island Heights cottage

                                                  1 6 min stay varies

                                                  • 1 bedroom
                                                  • sleeps 6
                                                  • min stay varies
                                                  • Swimming pool
                                                  • Child Friendly
                                                  • Air conditioning

                                                  Price per night from

                                                  $441

                                                  Responds fast!
                                                  avg. 8 minutes

                                                  Price per night from

                                                  $441

                                                  (1) Excellent 

                                                    26

                                                    East Hampton/Sag Harbor Village Fringe

                                                    Hamptons / Sag Harbor

                                                    Sag Harbor house

                                                    6 12 6 nights min

                                                    • 6 bedrooms
                                                    • sleeps 12
                                                    • 6 nights min
                                                    • Nearest beach 3 mi
                                                    • Swimming pool
                                                    • Child Friendly

                                                    Price per night from

                                                    $3,452

                                                    Responds fast!
                                                    avg. 3 hours 39 minutes

                                                    Price per night from

                                                    $3,452

                                                      24

                                                      Spacious Amagansett Home w/ Pool - Walk to Beach!

                                                      Hamptons / Amagansett

                                                      Amagansett house

                                                      6 12 7 nights min

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

                                                      Price per night from

                                                      $848

                                                      Responds fast!
                                                      avg. 58 minutes

                                                      Price per night from

                                                      $848

                                                        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

                                                        $10,001

                                                        Responds fast!
                                                        avg. 2 hours 51 minutes

                                                        Price per night from

                                                        $10,001

                                                          44

                                                          Private Home In Sag Harbor / Southampton With Pool & Jacuzzi

                                                          Hamptons / Sag Harbor

                                                          Sag Harbor house

                                                          6 12 min stay varies

                                                          • 6 bedrooms
                                                          • sleeps 12
                                                          • min stay varies
                                                          • Swimming pool
                                                          • Child Friendly
                                                          • Air conditioning

                                                          Price per night from

                                                          $932

                                                          Responds fast!
                                                          avg. 2 hours 39 minutes

                                                          Price per night from

                                                          $932

                                                            16

                                                            LOFT Style Apartment near JFK, NYC and Beaches!

                                                            Long Island / Freeport

                                                            Freeport apartment

                                                            2 6 2 nights min

                                                            • 2 bedrooms
                                                            • sleeps 6
                                                            • 2 nights min
                                                            • Nearest beach 7 mi
                                                            • Swimming pool
                                                            • Child Friendly

                                                            Price per night from

                                                            $194

                                                            Responds fast!
                                                            avg. 1 hour 14 minutes

                                                            Price per night from

                                                            $194

                                                            (2) Excellent 

                                                              45

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

                                                              Hamptons / Westhampton Beach

                                                              Westhampton Beach house

                                                              8 20 min stay varies

                                                              • 8 bedrooms
                                                              • sleeps 20
                                                              • min stay varies
                                                              • Beach / lakeside relaxation
                                                              • Swimming pool
                                                              • Child Friendly

                                                              Price per night from

                                                              $1,500

                                                              Price per night from

                                                              $1,500

                                                                13

                                                                Peaceful, charming, convenient

                                                                Hamptons / Bridgehampton

                                                                Bridgehampton house

                                                                5 10 5 nights min

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

                                                                Price per night from

                                                                $1,374

                                                                Price per night from

                                                                $1,374

                                                                  15

                                                                  chic, comfortable home with pool

                                                                  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

                                                                  $590

                                                                  Price per night from

                                                                  $590

                                                                    26

                                                                    Luxurious ‘Shelter Island Hideaway’ w/ Pool!

                                                                    Hamptons / Shelter Island

                                                                    Shelter Island house

                                                                    4 10 min stay varies

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

                                                                    Price per night from

                                                                    $567

                                                                    Responds fast!
                                                                    avg. 8 minutes

                                                                    Price per night from

                                                                    $567

                                                                    (5) Excellent 

                                                                      28

                                                                      Elegant Designer Hamptons Retreat in Sag Harbor

                                                                      Hamptons / Sag Harbor

                                                                      Sag Harbor house

                                                                      5 12 7 nights min

                                                                      • 5 bedrooms
                                                                      • sleeps 12
                                                                      • 7 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Nearest beach 1 mi
                                                                      • Swimming pool
                                                                      “Excellent vacation!” Beautifully decorated Designer home was fully furnished with great touches you would expect in a high end rental--soft linens and towels, mini ipods in docking stations around the house, fully stocked kitchen, fabulous pool and ba
                                                                      …see more

                                                                      Price per night from

                                                                      $2,782

                                                                      Responds fast!
                                                                      avg. 2 hours 39 minutes

                                                                      Price per night from

                                                                      $2,782

                                                                      (4) Excellent 

                                                                        16

                                                                        Ground floor sunlit apt. in great area!

                                                                        Long Island / Huntington

                                                                        Huntington apartment

                                                                        1 4 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 1 night min
                                                                        • Swimming pool
                                                                        • Ask about children
                                                                        • Ask about pets

                                                                        Price per night from

                                                                        $98

                                                                        Responds fast!
                                                                        avg. 3 hours 8 minutes

                                                                        Price per night from

                                                                        $98

                                                                        (2) Excellent 

                                                                          14

                                                                          Sag Harbor designer home, Chef's kitchen & one block from the water

                                                                          Hamptons / Sag Harbor

                                                                          Sag Harbor house

                                                                          5 10 1 night min

                                                                          • 5 bedrooms
                                                                          • sleeps 10
                                                                          • 1 night min
                                                                          • Swimming pool
                                                                          • Child Friendly
                                                                          • Air conditioning

                                                                          Price per night from

                                                                          $1,890

                                                                          Responds fast!
                                                                          avg. 3 hours 18 minutes

                                                                          Price per night from

                                                                          $1,890

                                                                            17

                                                                            Charming Cottage

                                                                            Hamptons / East Hampton

                                                                            East Hampton cottage

                                                                            1 4 1 night min

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

                                                                            Price per night from

                                                                            $173

                                                                            Price per night from

                                                                            $173

                                                                              12

                                                                              Vacation house with pool

                                                                              Southampton / Hampton Bays

                                                                              Hampton Bays house

                                                                              3 6 min stay varies

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

                                                                              Price per night from

                                                                              $344

                                                                              Price per night from

                                                                              $344