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  • Showing 1-50 of 300+
Additional fees apply. Taxes may be added.
    House #425548vb
    • 5 BR
    • 3 BA
    • Sleeps 10
    14

    Confirmation within 24 hours

    Your booking request will be confirmed or denied within 24 hours.

      House #4154990
      • 4 BR
      • 4 BA
      • 1 HF BA
      • Sleeps 10
      3
        House #321313vb
        • 3 BR
        • 2 BA
        • Sleeps 6
        3

        Confirmation within 24 hours

        Your booking request will be confirmed or denied within 24 hours.

          House #602844vb
          • 4 BR
          • 2 BA
          • 1 HF BA
          • Sleeps 9
          13

          Confirmation within 24 hours

          Your booking request will be confirmed or denied within 24 hours.

            House #746110vb
            • 4 BR
            • 3 BA
            • 2 HF BA
            • Sleeps 8
            9

            Confirmation within 24 hours

            Your booking request will be confirmed or denied within 24 hours.

              House #722961vb
              • 4 BR
              • 3 BA
              • 1 HF BA
              • Sleeps 10
                House #352116vb
                • 4 BR
                • 3 BA
                • Sleeps 7
                10
                  House #115762
                  • 5 BR
                  • 3 BA
                  • Sleeps 12
                  1
                    Bungalow #804815vb
                    • 3 BR
                    • 2 BA
                    • Sleeps 8
                    19

                    Confirmation within 24 hours

                    Your booking request will be confirmed or denied within 24 hours.

                      House #3925407
                      • 3 BR
                      • 1 BA
                      • Sleeps 8
                      6

                      Confirmation within 24 hours

                      Your booking request will be confirmed or denied within 24 hours.

                        House #694738vb
                        • 3 BR
                        • 1 BA
                        • Sleeps 6
                        8

                        Confirmation within 24 hours

                        Your booking request will be confirmed or denied within 24 hours.

                          House #3554393
                          • 3 BR
                          • 2 BA
                          • Sleeps 5
                          14

                          Confirmation within 24 hours

                          Your booking request will be confirmed or denied within 24 hours.

                            House #3621885
                            • 3 BR
                            • 2 BA
                            • 1 HF BA
                            • Sleeps 8
                            7

                            Confirmation within 24 hours

                            Your booking request will be confirmed or denied within 24 hours.

                              House #803084vb
                              • 3 BR
                              • 2 BA
                              • Sleeps 6
                              1

                              Confirmation within 24 hours

                              Your booking request will be confirmed or denied within 24 hours.

                                House #305998vb
                                • 3 BR
                                • 3 BA
                                • Sleeps 10
                                8

                                Confirmation within 24 hours

                                Your booking request will be confirmed or denied within 24 hours.

                                  House #446286vb
                                  • 4 BR
                                  • 2 BA
                                  • Sleeps 10
                                  8

                                  Confirmation within 24 hours

                                  Your booking request will be confirmed or denied within 24 hours.

                                    House #891646vb
                                    • 3 BR
                                    • 2 BA
                                    • Sleeps 6

                                    Confirmation within 24 hours

                                    Your booking request will be confirmed or denied within 24 hours.

                                      House #3781403
                                      • 5 BR
                                      • 3 BA
                                      • Sleeps 10
                                      2

                                      Confirmation within 24 hours

                                      Your booking request will be confirmed or denied within 24 hours.

                                        Apartment #830564vb
                                        • 3 BR
                                        • 2 BA
                                        • Sleeps 6

                                        Confirmation within 24 hours

                                        Your booking request will be confirmed or denied within 24 hours.

                                          House #90560vb
                                          • 3 BR
                                          • 2 BA
                                          • 1 HF BA
                                          • Sleeps 6
                                          2

                                          Confirmation within 24 hours

                                          Your booking request will be confirmed or denied within 24 hours.

                                            House #470387vb
                                            • 3 BR
                                            • Sleeps 8
                                            2

                                            Confirmation within 24 hours

                                            Your booking request will be confirmed or denied within 24 hours.

                                              Cottage #597850vb
                                              • 2 BR
                                              • 1 BA
                                              • Sleeps 6
                                              9

                                              Confirmation within 24 hours

                                              Your booking request will be confirmed or denied within 24 hours.

                                                House #3931482
                                                • 4 BR
                                                • 2 BA
                                                • Sleeps 8
                                                2

                                                Confirmation within 24 hours

                                                Your booking request will be confirmed or denied within 24 hours.

                                                  House #3942991
                                                  • 4 BR
                                                  • 1 BA
                                                  • Sleeps 8
                                                  4

                                                  Confirmation within 24 hours

                                                  Your booking request will be confirmed or denied within 24 hours.

                                                    House #344072vb
                                                    • 5 BR
                                                    • 4 BA
                                                    • Sleeps 12
                                                    5

                                                    Confirmation within 24 hours

                                                    Your booking request will be confirmed or denied within 24 hours.

                                                      House #676220vb
                                                      • 3 BR
                                                      • 2 BA
                                                      • Sleeps 8
                                                      1

                                                      Confirmation within 24 hours

                                                      Your booking request will be confirmed or denied within 24 hours.

                                                        House #698921vb
                                                        • 3 BR
                                                        • 2 BA
                                                        • Sleeps 6
                                                        1

                                                        Confirmation within 24 hours

                                                        Your booking request will be confirmed or denied within 24 hours.

                                                          Cottage #702619vb
                                                          • 3 BR
                                                          • 2 BA
                                                          • Sleeps 6
                                                          7

                                                          Confirmation within 24 hours

                                                          Your booking request will be confirmed or denied within 24 hours.

                                                            House #716643vb
                                                            • 5 BR
                                                            • 3 BA
                                                            • 1 HF BA
                                                            • Sleeps 10
                                                            8

                                                            Confirmation within 24 hours

                                                            Your booking request will be confirmed or denied within 24 hours.

                                                              House #476247vb
                                                              • 4 BR
                                                              • 3 BA
                                                              • Sleeps 10
                                                              10

                                                              Confirmation within 24 hours

                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                House #628856vb
                                                                • 5 BR
                                                                • 2 BA
                                                                • Sleeps 12
                                                                5

                                                                Confirmation within 24 hours

                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                  House #3596889
                                                                  • 2 BR
                                                                  • 2 BA
                                                                  • Sleeps 4

                                                                  Confirmation within 24 hours

                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                    House #885475vb
                                                                    • 3 BR
                                                                    • 3 BA
                                                                    • Sleeps 6

                                                                    Confirmation within 24 hours

                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                      House #908170vb
                                                                      • 3 BR
                                                                      • 2 BA
                                                                      • Sleeps 7
                                                                      1

                                                                      Confirmation within 24 hours

                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                        House #137734vb
                                                                        • 4 BR
                                                                        • 3 BA
                                                                        • 1 HF BA
                                                                        • Sleeps 8
                                                                        7

                                                                        Confirmation within 24 hours

                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                          House #411447vb
                                                                          • 4 BR
                                                                          • 3 BA
                                                                          • Sleeps 8
                                                                          6

                                                                          Confirmation within 24 hours

                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                            House #989574
                                                                            • 4 BR
                                                                            • 3 BA
                                                                            • Sleeps 8
                                                                            4

                                                                            Confirmation within 24 hours

                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                              Cottage #4062137
                                                                              • 4 BR
                                                                              • 2 BA
                                                                              • Sleeps 8
                                                                              2

                                                                              Confirmation within 24 hours

                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                House #672071vb
                                                                                • 7 BR
                                                                                • 4 BA
                                                                                • Sleeps 15

                                                                                Confirmation within 24 hours

                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                  House #363251vb
                                                                                  • 4 BR
                                                                                  • 2 BA
                                                                                  • Sleeps 6
                                                                                  6

                                                                                  Confirmation within 24 hours

                                                                                  Your booking request will be confirmed or denied within 24 hours.

                                                                                    Cottage #556885vb
                                                                                    • 4 BR
                                                                                    • 2 BA
                                                                                    • Sleeps 8
                                                                                    1

                                                                                    Confirmation within 24 hours

                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                      House #474895vb
                                                                                      • 4 BR
                                                                                      • 2 BA
                                                                                      • Sleeps 5

                                                                                      Confirmation within 24 hours

                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                        House #3684564
                                                                                        • 2 BR
                                                                                        • 1 BA
                                                                                        • Sleeps 4
                                                                                        5

                                                                                        Confirmation within 24 hours

                                                                                        Your booking request will be confirmed or denied within 24 hours.

                                                                                          House #4327666
                                                                                          • 3 BR
                                                                                          • 3 BA
                                                                                          • 2 HF BA
                                                                                          • Sleeps 8

                                                                                          Confirmation within 24 hours

                                                                                          Your booking request will be confirmed or denied within 24 hours.

                                                                                            House #857206vb
                                                                                            • 4 BR
                                                                                            • 2 BA
                                                                                            • Sleeps 8

                                                                                            Confirmation within 24 hours

                                                                                            Your booking request will be confirmed or denied within 24 hours.

                                                                                              House #338964vb
                                                                                              • 3 BR
                                                                                              • 2 BA
                                                                                              • Sleeps 7
                                                                                              5

                                                                                              Confirmation within 24 hours

                                                                                              Your booking request will be confirmed or denied within 24 hours.

                                                                                                House #3757374
                                                                                                • 4 BR
                                                                                                • 4 BA
                                                                                                • 1 HF BA
                                                                                                • Sleeps 7
                                                                                                3

                                                                                                Confirmation within 24 hours

                                                                                                Your booking request will be confirmed or denied within 24 hours.

                                                                                                  House #422449vb
                                                                                                  • 4 BR
                                                                                                  • 3 BA
                                                                                                  • Sleeps 10
                                                                                                  4

                                                                                                  Confirmation within 24 hours

                                                                                                  Your booking request will be confirmed or denied within 24 hours.

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                                                                                                    House #829820vb
                                                                                                    • 4 BR
                                                                                                    • 3 BA
                                                                                                    • Sleeps 8

                                                                                                    Confirmation within 24 hours

                                                                                                    Your booking request will be confirmed or denied within 24 hours.

                                                                                                      Chateau / Country House #4202867
                                                                                                      • 4 BR
                                                                                                      • 3 BA
                                                                                                      • Sleeps 7
                                                                                                      1

                                                                                                      Confirmation within 24 hours

                                                                                                      Your booking request will be confirmed or denied within 24 hours.

                                                                                                      • 1 - 50 of 300+

                                                                                                      Shelter Island Vacation Rentals (300+)