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  • Showing 1-50 of 51
Additional fees apply. Taxes may be added.
    Wonderful! 4.8/5
    (13 reviews)
    avg/night
    • 4 BR
    • 2 BA
    • Sleeps 10
    Estate #407512vb
    13
    Viewed 54 times in the last 48 hours
      Exceptional! 5.0/5
      (15 reviews)
      avg/night
      • 7 BR
      • 6 BA
      • 1 HF BA
      • Sleeps 14
      Estate #3015973
      15
      Viewed 121 times in the last 48 hours
        Wonderful! 4.9/5
        (17 reviews)
        avg/night
        • 2 BR
        • 1 BA
        • Sleeps 5
        Estate #718247vb
        17
        Viewed 16 times in the last 48 hours
          avg/night
          • 5 BR
          • 5 BA
          • 1 HF BA
          • Sleeps 10
          Estate #281507
          3
          Viewed 37 times in the last 48 hours
            Wonderful! 4.9/5
            (14 reviews)
            avg/night
            • 6 BR
            • 4 BA
            • 2 HF BA
            • Sleeps 12
            Estate #243063
            14
            Viewed 11 times in the last 48 hours
              • 5 BR
              • 4 BA
              • Sleeps 10
              Estate #324809
              0
              Viewed 68 times in the last 48 hours
                Exceptional! 5.0/5
                (8 reviews)
                avg/night
                • 5 BR
                • 4 BA
                • 2 HF BA
                • Sleeps 10
                Estate #224587
                8
                Viewed 14 times in the last 48 hours
                  avg/night
                  • 5 BR
                  • 5 BA
                  • Sleeps 8
                  Estate #719879vb
                  1
                  Viewed 7 times in the last 48 hours
                    • 4 BR
                    • 3 BA
                    • 1 HF BA
                    • Sleeps 8
                    Estate #669887vb
                    0
                    Viewed 27 times in the last 48 hours
                      Exceptional! 5.0/5
                      (7 reviews)
                      avg/night
                      • 5 BR
                      • 4 BA
                      • Sleeps 10
                      Estate #473208vb
                      7
                      Viewed 26 times in the last 48 hours
                        avg/night
                        • 5 BR
                        • 5 BA
                        • 1 HF BA
                        • Sleeps 10
                        Estate #593627vb
                        4
                        Viewed 29 times in the last 48 hours
                          Exceptional! 5.0/5
                          (7 reviews)
                          avg/night
                          • 4 BR
                          • 3 BA
                          • 1 HF BA
                          • Sleeps 8
                          Estate #4116412
                          7
                          Viewed 16 times in the last 48 hours
                            avg/night
                            • 6 BR
                            • 5 BA
                            • Sleeps 12
                            Estate #893318vb
                            1
                            Viewed 7 times in the last 48 hours
                              • 3 BR
                              • 2 BA
                              • 1 HF BA
                              • Sleeps 6
                              Estate #3606087
                              1
                              Viewed 52 times in the last 48 hours
                                avg/night
                                • 5 BR
                                • 3 BA
                                • Sleeps 12
                                Estate #4289641
                                0
                                Viewed 24 times in the last 48 hours
                                  • 5 BR
                                  • 4 BA
                                  • Sleeps 6
                                  Estate #853939vb
                                  0
                                  Viewed 32 times in the last 48 hours
                                    avg/night
                                    • 6 BR
                                    • 7 BA
                                    • Sleeps 12
                                    Estate #866861vb
                                    0
                                    Viewed 8 times in the last 48 hours
                                      • 6 BR
                                      • 4 BA
                                      • 1 HF BA
                                      • Sleeps 10
                                      Estate #874993vb
                                      0
                                        • 4 BR
                                        • 2 BA
                                        • 2 HF BA
                                        • Sleeps 8
                                        Estate #4175985
                                        0
                                          • 4 BR
                                          • 3 BA
                                          • 1 HF BA
                                          • Sleeps 9
                                          Estate #472238vb
                                          0
                                            • 4 BR
                                            • 4 BA
                                            • Sleeps 8
                                            Estate #829029vb
                                            0
                                              Exceptional! 5.0/5
                                              (5 reviews)
                                              avg/night
                                              • 4 BR
                                              • 2 BA
                                              • Sleeps 9
                                              Estate #341678vb
                                              5
                                              Viewed 18 times in the last 48 hours
                                                • 4 BR
                                                • 4 BA
                                                • Sleeps 8
                                                Estate #881776vb
                                                0
                                                  • 5 BR
                                                  • 5 BA
                                                  • Sleeps 10
                                                  Estate #986991vb
                                                  0
                                                    avg/night
                                                    • 6 BR
                                                    • 6 BA
                                                    • 1 HF BA
                                                    • Sleeps 14
                                                    Estate #841632vb
                                                    0
                                                    Viewed 16 times in the last 48 hours
                                                      Exceptional! 5.0/5
                                                      (6 reviews)
                                                      avg/night
                                                      • 7 BR
                                                      • 5 BA
                                                      • Sleeps 18
                                                      Estate #205195
                                                      6
                                                      Viewed 43 times in the last 48 hours
                                                        avg/night
                                                        • 5 BR
                                                        • 4 BA
                                                        • Sleeps 11
                                                        Estate #734895vb
                                                        0
                                                        Viewed 7 times in the last 48 hours
                                                          Wonderful! 4.9/5
                                                          (8 reviews)
                                                          avg/night
                                                          • 7 BR
                                                          • 4 BA
                                                          • 2 HF BA
                                                          • Sleeps 18
                                                          Estate #100556
                                                          8
                                                          Viewed 21 times in the last 48 hours
                                                            avg/night
                                                            • 9 BR
                                                            • 4 BA
                                                            • Sleeps 18
                                                            Estate #4070617
                                                            0
                                                            Viewed 7 times in the last 48 hours
                                                              avg/night
                                                              • 7 BR
                                                              • 4 BA
                                                              • Sleeps 14
                                                              Estate #4070609
                                                              0
                                                              Viewed 7 times in the last 48 hours
                                                                Exceptional! 5.0/5
                                                                (10 reviews)
                                                                avg/night
                                                                • 7 BR
                                                                • 5 BA
                                                                • Sleeps 16
                                                                Estate #108713
                                                                10
                                                                Viewed 8 times in the last 48 hours
                                                                  Exceptional! 5.0/5
                                                                  (7 reviews)
                                                                  avg/night
                                                                  • 8 BR
                                                                  • 6 BA
                                                                  • Sleeps 20
                                                                  Estate #3903370
                                                                  7
                                                                  Viewed 47 times in the last 48 hours
                                                                    avg/night
                                                                    • 9 BR
                                                                    • 7 BA
                                                                    • Sleeps 14
                                                                    Estate #3927179
                                                                    0
                                                                    Viewed 5 times in the last 48 hours
                                                                      avg/night
                                                                      • 10 BR
                                                                      • 9 BA
                                                                      • Sleeps 20
                                                                      Estate #835752vb
                                                                      0
                                                                      Viewed 166 times in the last 48 hours
                                                                        • 7 BR
                                                                        • 6 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 16
                                                                        Estate #459326vb
                                                                        2
                                                                        Viewed 10 times in the last 48 hours
                                                                          • 6 BR
                                                                          • 6 BA
                                                                          • 1 HF BA
                                                                          • Sleeps 18
                                                                          Estate #984046
                                                                          0
                                                                            • 8 BR
                                                                            • 4 BA
                                                                            • 1 HF BA
                                                                            • Sleeps 16
                                                                            Estate #4030893
                                                                            0
                                                                            Viewed 22 times in the last 48 hours
                                                                              avg/night
                                                                              • 6 BR
                                                                              • 5 BA
                                                                              • 1 HF BA
                                                                              • Sleeps 18
                                                                              Estate #371247vb
                                                                              0
                                                                              Viewed 18 times in the last 48 hours
                                                                                • 5 BR
                                                                                • 6 BA
                                                                                • Sleeps 14
                                                                                Estate #4222881
                                                                                0
                                                                                  avg/night
                                                                                  • 4 BR
                                                                                  • 3 BA
                                                                                  • Sleeps 10
                                                                                  Estate #454887vb
                                                                                  0
                                                                                  Viewed 7 times in the last 48 hours
                                                                                    View details for price
                                                                                    • 4 BR
                                                                                    • 4 BA
                                                                                    • 1 HF BA
                                                                                    • Sleeps 8
                                                                                    Estate #469389vb
                                                                                    0
                                                                                    Viewed 5 times in the last 48 hours
                                                                                      • 8 BR
                                                                                      • 8 BA
                                                                                      • 3 HF BA
                                                                                      • Sleeps 16
                                                                                      Estate #3967095
                                                                                      0
                                                                                      Viewed 28 times in the last 48 hours
                                                                                        Excellent! 4.5/5
                                                                                        (11 reviews)
                                                                                        avg/night
                                                                                        • 5 BR
                                                                                        • 4 BA
                                                                                        • 1 HF BA
                                                                                        • Sleeps 14
                                                                                        Estate #83848vb
                                                                                        11
                                                                                        Viewed 100 times in the last 48 hours
                                                                                          avg/night
                                                                                          • 6 BR
                                                                                          • 5 BA
                                                                                          • 1 HF BA
                                                                                          • Sleeps 10
                                                                                          Estate #899214vb
                                                                                          0
                                                                                          Viewed 5 times in the last 48 hours
                                                                                            • 5 BR
                                                                                            • 6 BA
                                                                                            • 1 HF BA
                                                                                            • Sleeps 10
                                                                                            Estate #466338vb
                                                                                            0
                                                                                            Viewed 18 times in the last 48 hours
                                                                                              • 5 BR
                                                                                              • 4 BA
                                                                                              • 1 HF BA
                                                                                              • Sleeps 9
                                                                                              Estate #287294
                                                                                              2
                                                                                                • 6 BR
                                                                                                • 5 BA
                                                                                                • 2 HF BA
                                                                                                • Sleeps 12
                                                                                                Estate #368872vb
                                                                                                0
                                                                                                Viewed 18 times in the last 48 hours
                                                                                                  avg/night
                                                                                                  • Studio
                                                                                                  • Sleeps 10
                                                                                                  Estate #458510vb
                                                                                                  0
                                                                                                  Viewed 13 times in the last 48 hours
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • 1 HF BA
                                                                                                    • Sleeps 8
                                                                                                    Estate #649011vb
                                                                                                    3
                                                                                                      View details for price
                                                                                                      • 8 BR
                                                                                                      • 7 BA
                                                                                                      • Sleeps 20
                                                                                                      Estate #380251
                                                                                                      0
                                                                                                      Viewed 22 times in the last 48 hours
                                                                                                      • 1 - 50 of 51

                                                                                                      Shelter Island: Vacation Rental Estates (51)

                                                                                                       

                                                                                                      Recent Shelter Island Reviews

                                                                                                      Perfect Fall Getaway!

                                                                                                      5 of 5
                                                                                                      We had such a wonderful stay at this house! We rented it to celebrate a 30th birthday with 11 close friends. The pictures really don't do it justice. The house was incredibly spacious, clean and fit all of our guests comfortably. We hung out on the deck quite a bit, played tennis and cooked in both nights we were there. The actual location of the house was very close to the Southampton village, which was great for grocery shopping. Gregg & Dave, who manage the property, were extremely accommodating and were very responsive before and during our stay. They made us feel like we were at home. We can't wait to go back again! Highly recommended!
                                                                                                      • Submitted: Dec 9, 2016
                                                                                                      • Stayed: Oct 2016

                                                                                                      Beautiful sunlit family home

                                                                                                      5 of 5
                                                                                                      Our family of six spent four wonderful weeks in this lovely home during the summer of 2016. The interior space is spacious and bright and the setting is very private with beautiful treeline views from the backyard. The pool is in the sun for almost the entire day. Daniel and his wife were also extremely helpful and responsive as we got settled in. We left with many great memories !
                                                                                                      • Submitted: Oct 17, 2016
                                                                                                      • Stayed: Jul 2016

                                                                                                      Amazing House

                                                                                                      5 of 5
                                                                                                      We where 4 copels that rented this beautiful house and had the best weekend ever in Hampton Bays. Great owners and great service. I can highly recommend this house for those who wants a nice weekend in the Hamptons.
                                                                                                      • Submitted: Sep 26, 2016
                                                                                                      • Stayed: Sep 2016