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Shelter Island Vacation Home Rentals(79)

79 Results
$8,400
per week
7 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 10
#485109vb
    1 Review
    7 night minimum stay
    • 5 BR,
    • 3 BA,
    • Sleeps 10
    #425548vb
      (9)
      14 night minimum stay
      • 6 BR,
      • 4 BA,
      • 2 HF BA,
      • Sleeps 12
      #3674314
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        21 night minimum stay
        • 5 BR,
        • 3 BA,
        • Sleeps 10
        #3781403
          7 night minimum stay
          • 3 BR,
          • 2 BA,
          • 1 HF BA,
          • Sleeps 4
          #407940vb
            2 Reviews
            Book it Now!
            14 - 30 night minimum stay
            • 3 BR,
            • 2 BA,
            • Sleeps 8
            #3783208
              3 - 14 night minimum stay
              • 4 BR,
              • 4 BA,
              • 1 HF BA,
              • Sleeps 10
              #3757374
                7 - 31 night minimum stay
                • 5 BR,
                • 3 BA,
                • Sleeps 12
                #115762
                  1 Review
                  Book it Now!
                  7 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 8
                  #3762430
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                    30 night minimum stay
                    • 4 BR,
                    • 3 BA,
                    • Sleeps 10
                    #591815vb
                      2 - 9 night minimum stay
                      • 4 BR,
                      • 3 BA,
                      • 2 HF BA,
                      • Sleeps 12
                      #189852
                        (5)
                        2 night minimum stay
                        • 3 BR,
                        • 3 BA,
                        • Sleeps 7
                        #944956
                          (4)
                          4 - 14 night minimum stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 7
                          #376553
                            (3)
                            Book it Now!
                            7 night minimum stay
                            • 4 BR,
                            • 4 BA,
                            • 1 HF BA,
                            • Sleeps 10
                            #573696vb
                              Book it Now!
                              3 - 30 night minimum stay
                              • 3 BR,
                              • 2 BA,
                              • Sleeps 6
                              #3554393
                                (3)
                                3 - 14 night minimum stay
                                • 3 BR,
                                • 2 BA,
                                • 1 HF BA,
                                • Sleeps 6
                                #370389
                                  (7)
                                  Book it Now!
                                  3 night minimum stay
                                  • 3 BR,
                                  • 2 BA,
                                  • 1 HF BA,
                                  • Sleeps 8
                                  #3621885
                                    1 Review
                                    Book it Now!
                                    3 night minimum stay
                                    • 2 BR,
                                    • 2 BA,
                                    • Sleeps 4
                                    #3596889
                                      Book it Now!
                                      7 night minimum stay
                                      • 6 BR,
                                      • 4 BA,
                                      • Sleeps 14
                                      #592030vb
                                        1 Review
                                        Book it Now!
                                        2 night minimum stay
                                        • 4 BR,
                                        • 2 BA,
                                        • 1 HF BA,
                                        • Sleeps 8
                                        #602844vb
                                          7 - 30 night minimum stay
                                          • 3 BR,
                                          • 2 BA,
                                          • Sleeps 6
                                          #250830
                                            1 Review
                                            27 - 30 night minimum stay
                                            • 4 BR,
                                            • 3 BA,
                                            • Sleeps 8
                                            #3531549
                                              3 night minimum stay
                                              • 3 BR,
                                              • 3 BA,
                                              • Sleeps 6
                                              #385658
                                                7 night minimum stay
                                                • 3 BR,
                                                • 3 BA,
                                                • Sleeps 6
                                                #3594708
                                                  3 night minimum stay
                                                  • 6 BR,
                                                  • 5 BA,
                                                  • Sleeps 18
                                                  #3801641
                                                    7 night minimum stay
                                                    • 3 BR,
                                                    • 2 BA,
                                                    • Sleeps 6
                                                    #248802
                                                      (3)
                                                      7 - 31 night minimum stay
                                                      • 5 BR,
                                                      • 4 BA,
                                                      • 1 HF BA,
                                                      • Sleeps 6
                                                      #159174
                                                        1 Review
                                                        3 - 31 night minimum stay
                                                        • 4 BR,
                                                        • 3 BA,
                                                        • Sleeps 9
                                                        #452492vb
                                                          1 Review
                                                          14 night minimum stay
                                                          • 3 BR,
                                                          • 3 BA,
                                                          • Sleeps 8
                                                          #364166
                                                            7 - 30 night minimum stay
                                                            • 5 BR,
                                                            • 3 BA,
                                                            • 1 HF BA,
                                                            • Sleeps 10
                                                            #3022336
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                                                              Recent Shelter Island Reviews

                                                              FANTASTIC HOLIDAY IN THIS HOUSE!

                                                              5 of 5
                                                              John the owner was wonderfully helpful from start to finish with our holiday to Shelter Island. He was unfazed that we were going to be five mommies and babies for the week and was on hand to answer questions all the time. The garden is beautiful, the rooms all airy and clean (excepting a great room in the basement without light which was great for babies to sleep in!) and from here we were able to do long strolls to Sunset Beach and to the spit on the south of the island. All round fabulous- highly recommended.
                                                              • Submitted: Jun 30, 2014
                                                              • Stayed: May 2014

                                                              ABSOLUTELY STUNNING!!

                                                              5 of 5
                                                              Beautiful light filled house, wonderfully decorated, all the comforts of home, close to the water and yet minutes to the shops and harbor cafes! We couldn't have wished for more, and can't reccomend it highly enough. Jane and Benjamin
                                                              • Submitted: Apr 25, 2014
                                                              • Stayed: Apr 2014

                                                              ONE OF THE BEST VACATIONS I HAVE HAD!!!

                                                              5 of 5
                                                              The place is incredible!!! I did not expect it to look 10 times better than the pictures on the website! It is well-taken care of, has everything you need to enjoy your vacation and more (kitchen has all appliances, bedrooms and bathrooms clean and fresh linens and towels, entertainment center, etc). It is close to the beach, not far from Montauk and LI wine country, and other great places for adults and children to enjoy. Although we explored all the places nearby and enjoyed being outside, I could see myself spending my whole vacation in the house. It is so peaceful and beautiful inside and outside! The owner was really accommodating, polite and attentive. Would go back to the place any time!
                                                              • Submitted: Sep 27, 2013
                                                              • Stayed: Sep 2013