Family Fun at Shelter Island Vacation Rentals

Shelter Island vacation rentals are located in the Hamptons on Long Island, New York. It is a great destination for a family vacation as there are many activities and attractions to keep the kids entertained. Shelter Island is primarily a summer vacation destination where families spend their days enjoying the beaches and spending quality time together.

Treasures of Nature near Shelter Island Vacation Rentals


Near Shelter Island house rentals, you can visit the Mashomack Preserve. The preserve makes up at least one-third of Shelter Island and is a beautiful wildlife sanctuary. Birding enthusiasts staying at Shelter Island Hamptons rentals can enjoy the nature trails and diverse habitats in the preserve. It is home to one of the largest breeding colonies of osprey on the East Coast. There are unique wetland habitats and swamps that provide a sanctuary for marine creatures, making for a valuable part of the ecosystem. When visiting the preserve from your Shelter Island beach rentals, take along comfortable walking shoes. The only way to explore the park is on designated nature trails.

Leisurely Summer Days at Shelter Island Hamptons Rentals


Because Shelter Island beach rentals are just a short drive away from New York City, it is a popular summer vacation destination. Often families make use of Shelter Island vacation rentals for an extended period during the summer months. The area has some beautiful beaches which are ideal for building sandcastles with the kids or enjoying long leisurely strolls. Many of Shelter Island beach rentals are conveniently located near restaurants and shops so you can dine out if you choose.

Water Sports Activities near Shelter Island Beach Rentals


Shelter Island vacation rentals provide the ideal bases from which to enjoy a variety of activities. Sailing is a popular pastime and yachts can be chartered at one of the local marinas. Many people who stay at Shelter Island Hamptons rentals are fishing enthusiasts. There are options for shoreline fishing or you can head out to deeper waters on a sport fishing charter boat. There are several areas that are designated as safe swimming beaches near Shelter Island beach rentals. This is a great way to cool off from the warm summer sun.

Find more Hamptons vacation rentals and include East Hampton rentals and Sag Harbor rentals in your search.

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Shelter Island: Houses, Cottages & More(85)

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Gorgeous Home in Beach Community with Heated Saltwater Pool
    4 Bedrooms,
  • 3 Bathrooms
    • , Sleeps 10
$5,950
per week

Gorgeous Home in Beach Community with Heated Saltwater Pool

7 - 31 night Minimum Stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
  1. Hamptons >
  2. Shelter Island House
#115762
    1 Review
    Romantic Waterfront Hideaway
      4 Bedrooms,
    • 7 Bathrooms
      • , Sleeps 14
    $5,500
    per week

    Romantic Waterfront Hideaway

    7 night Minimum Stay
    • 4 BR,
    • 7 BA,
    • Sleeps 14
    1. Hamptons >
    2. Shelter Island Chateau / Country House
    #3539427
      Airy + Light Island Retreat, Walk to Sunset Beach -MEM DAY WKND AVAIL !
        3 Bedrooms,
      • 3 Bathrooms
        • , Sleeps 7
      $500
      per night

      Airy + Light Island Retreat, Walk to Sunset Beach -MEM DAY WKND AVAIL !

      3 - 7 night Minimum Stay
      • 3 BR,
      • 3 BA,
      • Sleeps 7
      1. Hamptons >
      2. Shelter Island House
      #326053
        2 Reviews
        Luxury,Quiet, Pool,Spotless, Beach,Main+Guest House,June Still Avail!
          6 Bedrooms,
        • 7 Bathrooms
          • , Sleeps 14
        $5,000 - $7,395
        per week

        Luxury,Quiet, Pool,Spotless, Beach,Main+Guest House,June Still Avail!

        2 - 7 night Minimum Stay
        • 6 BR,
        • 7 BA,
        • Sleeps 14
        1. Hamptons >
        2. Shelter Island Estate
        #3505246
          (5)
          Contemporary Home With Old Vocabulary In Walking Distance To Beaches
            4 Bedrooms,
          • 3 Bathrooms
            • , Sleeps 8
          $6,000 - $11,000
          per month

          Contemporary Home With Old Vocabulary In Walking Distance To Beaches

          28 night Minimum Stay
          • 4 BR,
          • 3 BA,
          • Sleeps 8
          1. Hamptons >
          2. Shelter Island House
          #3531549
            Private Beautiful Home 2 Acres With Large Pool, Walk To Wades Beach
              4 Bedrooms, Sleeps 10
            $15,000 - $25,000
            per month

            Private Beautiful Home 2 Acres With Large Pool, Walk To Wades Beach

            14 night Minimum Stay
            • 4 BR,
            • Sleeps 10
            1. Hamptons >
            2. Shelter Island Estate
            #472283vb
              Contemporary luxury home with pool in the Heights
                4 Bedrooms,
              • 4 Bathrooms, 
              • 1 Half Bath
                • , Sleeps 8
              $1,000 - $3,000
              per night

              Contemporary luxury home with pool in the Heights

              3 night Minimum Stay
              • 4 BR,
              • 4 BA,
              • 1 HF BA,
              • Sleeps 8
              1. Hamptons >
              2. Shelter Island House
              #980204
                (4)
                Design and Comfort Come Together in this Island Beach Home
                  3 Bedrooms,
                • 3 Bathrooms
                  • , Sleeps 7
                $2,800 - $4,750
                per week

                Design and Comfort Come Together in this Island Beach Home

                7 night Minimum Stay
                • 3 BR,
                • 3 BA,
                • Sleeps 7
                1. Hamptons >
                2. Shelter Island House
                #944956
                  (3)
                  Shelter Island Renovated Barn Hideaway Pool • Water Access • Hamptons
                    2 Bedrooms,
                  • 2 Bathrooms
                    • , Sleeps 6
                  $11,029 - $19,375
                  per month

                  Shelter Island Renovated Barn Hideaway Pool • Water Access • Hamptons

                  14 - 31 night Minimum Stay
                  • 2 BR,
                  • 2 BA,
                  • Sleeps 6
                  1. Hamptons >
                  2. Shelter Island Barn
                  #998344
                    Eclectic Round House- 4 Bedroom+Cottage+Pool on 1.5 Priv Acres
                      4 Bedrooms,
                    • 3 Bathrooms, 
                    • 1 Half Bath
                      • , Sleeps 10

                    Eclectic Round House- 4 Bedroom+Cottage+Pool on 1.5 Priv Acres

                    • 4 BR,
                    • 3 BA,
                    • 1 HF BA,
                    • Sleeps 10
                    1. Hamptons >
                    2. Shelter Island House
                    #390379vb
                      Two Acre Waterfront Estate with Renovated Historic Home, Shelter Island NY
                        4 Bedrooms,
                      • 3 Bathrooms
                        • , Sleeps 7
                      $2,700 - $10,000
                      per week

                      Two Acre Waterfront Estate with Renovated Historic Home, Shelter Island NY

                      7 - 28 night Minimum Stay
                      • 4 BR,
                      • 3 BA,
                      • Sleeps 7
                      1. Hamptons >
                      2. Shelter Island House
                      #376553
                        2 Reviews
                        Nature Lover's Delight!
                          3 Bedrooms,
                        • 2 Bathrooms, 
                        • 1 Half Bath
                          • , Sleeps 6
                        $3,500 - $5,425
                        per week

                        Nature Lover's Delight!

                        7 night Minimum Stay
                        • 3 BR,
                        • 2 BA,
                        • 1 HF BA,
                        • Sleeps 6
                        1. Hamptons >
                        2. Shelter Island Cottage
                        #3558053
                          Beautiful, Secluded, Waterfront with Wrap-around Porch and Roof Deck
                            4 Bedrooms,
                          • 3 Bathrooms
                            • , Sleeps 9
                          $1,000
                          per night

                          Beautiful, Secluded, Waterfront with Wrap-around Porch and Roof Deck

                          3 night Minimum Stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 9
                          1. Hamptons >
                          2. Shelter Island House
                          #452492vb
                            Spacious Shelter Island Escape within walking distance to pristine beach
                              4 Bedrooms,
                            • 2 Bathrooms
                              • , Sleeps 10
                            $2,250 - $2,650
                            per week

                            Spacious Shelter Island Escape within walking distance to pristine beach

                            7 night Minimum Stay
                            • 4 BR,
                            • 2 BA,
                            • Sleeps 10
                            1. Hamptons >
                            2. Shelter Island House
                            #906013
                              1 Review
                              Charming, Historic Cottage
                                3 Bedrooms,
                              • 2 Bathrooms
                                • , Sleeps 6
                              $250 - $300
                              per night

                              Charming, Historic Cottage

                              2 - 7 night Minimum Stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 6
                              1. Hamptons >
                              2. Shelter Island Cottage
                              #3525659
                                Tranquil Island Refuge Nestled Among Towering Trees and Near Private Beach
                                  3 Bedrooms,
                                • 2 Bathrooms
                                  • , Sleeps 6
                                $1,900 - $2,575
                                per week

                                Tranquil Island Refuge Nestled Among Towering Trees and Near Private Beach

                                3 - 7 night Minimum Stay
                                • 3 BR,
                                • 2 BA,
                                • Sleeps 6
                                1. Hamptons >
                                2. Shelter Island House
                                #248802
                                  1 Review
                                  Winner of Best of Citysearch- Beach/Pool, 4+ Bedroom Hamptons Vacation
                                    5 Bedrooms,
                                  • 4 Bathrooms
                                    • , Sleeps 10
                                  $400 - $695
                                  per night

                                  Winner of Best of Citysearch- Beach/Pool, 4+ Bedroom Hamptons Vacation

                                  3 - 7 night Minimum Stay
                                  • 5 BR,
                                  • 4 BA,
                                  • Sleeps 10
                                  1. Hamptons >
                                  2. Shelter Island House
                                  #184172
                                    (4)
                                    Stylish Shelter Island Home with Pool and Walk to Beach.
                                      3 Bedrooms,
                                    • 2 Bathrooms, 
                                    • 1 Half Bath
                                      • , Sleeps 6

                                    Stylish Shelter Island Home with Pool and Walk to Beach.

                                    • 3 BR,
                                    • 2 BA,
                                    • 1 HF BA,
                                    • Sleeps 6
                                    1. Hamptons >
                                    2. Shelter Island House
                                    #370389
                                      (6)
                                      Charming Cottage. June available. Can rent year around.
                                        3 Bedrooms,
                                      • 1 Bathroom
                                        • , Sleeps 3
                                      $5,002 - $5,075
                                      per month

                                      Charming Cottage. June available. Can rent year around.

                                      29 night Minimum Stay
                                      • 3 BR,
                                      • 1 BA,
                                      • Sleeps 3
                                      1. Hamptons >
                                      2. Shelter Island Cottage
                                      #999295
                                        ROMANTIC Hamptons Beach Cottage! Seclusion, Waterfalls
                                          2 Bedrooms,
                                        • 1 Bathroom, 
                                        • 1 Half Bath
                                          • , Sleeps 6
                                        $335 - $495
                                        per night

                                        ROMANTIC Hamptons Beach Cottage! Seclusion, Waterfalls

                                        2 - 7 night Minimum Stay
                                        • 2 BR,
                                        • 1 BA,
                                        • 1 HF BA,
                                        • Sleeps 6
                                        1. Hamptons >
                                        2. Shelter Island Cottage
                                        #3513499
                                          Walk to Sunset Beach: Perfect Family Getaway: Historic Colonial
                                            4 Bedrooms,
                                          • 2 Bathrooms
                                            • , Sleeps 10
                                          $200 - $350
                                          per night

                                          Walk to Sunset Beach: Perfect Family Getaway: Historic Colonial

                                          2 - 3 night Minimum Stay
                                          • 4 BR,
                                          • 2 BA,
                                          • Sleeps 10
                                          1. Hamptons >
                                          2. Shelter Island House
                                          #446286vb
                                            Adorable Waterfront Cottage
                                              2 Bedrooms,
                                            • 1 Bathroom
                                              • , Sleeps 6

                                            Adorable Waterfront Cottage

                                            • 2 BR,
                                            • 1 BA,
                                            • Sleeps 6
                                            1. Hamptons >
                                            2. Shelter Island
                                            #391665
                                              2 Reviews
                                              Rustic house w/ pool on 2 private acres
                                                3 Bedrooms,
                                              • 2 Bathrooms
                                                • , Sleeps 6
                                              $8,000 - $15,000
                                              per month

                                              Rustic house w/ pool on 2 private acres

                                              3 - 28 night Minimum Stay
                                              • 3 BR,
                                              • 2 BA,
                                              • Sleeps 6
                                              1. Hamptons >
                                              2. Shelter Island House
                                              #250830
                                                1 Review
                                                Very elegant, with hot tub, large deck and lush landscape
                                                  3 Bedrooms,
                                                • 3 Bathrooms
                                                  • , Sleeps 8
                                                $2,500 - $3,500
                                                per week

                                                Very elegant, with hot tub, large deck and lush landscape

                                                2 - 7 night Minimum Stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 8
                                                1. Hamptons >
                                                2. Shelter Island House
                                                #385658
                                                  Charming Water View Victorian ' Eden Roc ' in Park-like-Setting
                                                    5 Bedrooms,
                                                  • 4 Bathrooms, 
                                                  • 1 Half Bath
                                                    • , Sleeps 6
                                                  $30,000 - $35,000
                                                  per month

                                                  Charming Water View Victorian ' Eden Roc ' in Park-like-Setting

                                                  7 night Minimum Stay
                                                  • 5 BR,
                                                  • 4 BA,
                                                  • 1 HF BA,
                                                  • Sleeps 6
                                                  1. Hamptons >
                                                  2. Shelter Island House
                                                  #159174
                                                    1 Review
                                                    Breathtaking & Charming Shelter Island Oasis 5BR 3.5BA on Private Acre
                                                      5 Bedrooms,
                                                    • 3 Bathrooms, 
                                                    • 1 Half Bath
                                                      • , Sleeps 10
                                                    $4,000 - $7,000
                                                    per week

                                                    Breathtaking & Charming Shelter Island Oasis 5BR 3.5BA on Private Acre

                                                    28 night Minimum Stay
                                                    • 5 BR,
                                                    • 3 BA,
                                                    • 1 HF BA,
                                                    • Sleeps 10
                                                    1. Hamptons >
                                                    2. Shelter Island House
                                                    #3022336
                                                      Waterfront Charmer on idyllic Shelter Island for summer rental
                                                        3 Bedrooms,
                                                      • 3 Bathrooms
                                                        • , Sleeps 8

                                                      Waterfront Charmer on idyllic Shelter Island for summer rental

                                                      • 3 BR,
                                                      • 3 BA,
                                                      • Sleeps 8
                                                      1. Hamptons >
                                                      2. Shelter Island House
                                                      #364166
                                                        6 Reviews
                                                        Relax by the Pool at This Comfortable 3 Bedroom Retreat
                                                          3 Bedrooms,
                                                        • 2 Bathrooms
                                                          • , Sleeps 8

                                                        Relax by the Pool at This Comfortable 3 Bedroom Retreat

                                                        • 3 BR,
                                                        • 2 BA,
                                                        • Sleeps 8
                                                        1. Hamptons >
                                                        2. Shelter Island Cottage
                                                        #3004585
                                                          (3)
                                                          Spectacular architects waterfront greek revival
                                                            5 Bedrooms,
                                                          • 4 Bathrooms
                                                            • , Sleeps 9

                                                          Spectacular architects waterfront greek revival

                                                          • 5 BR,
                                                          • 4 BA,
                                                          • Sleeps 9
                                                          1. Hamptons >
                                                          2. Shelter Island House
                                                          #227764
                                                            Sun Worshipers Paradise
                                                              3 Bedrooms,
                                                            • 1 Bathroom, 
                                                            • 1 Half Bath
                                                              • , Sleeps 6

                                                            Sun Worshipers Paradise

                                                            • 3 BR,
                                                            • 1 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 6
                                                            1. Hamptons >
                                                            2. Shelter Island House
                                                            #238094
                                                              1 Review
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