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Shelter Island Beach Vacation Rentals Vacation Rentals(38)

38 Results
7 - 31 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 12
    1 Review
    Book it Now!
    • 5 BR,
    • 3 BA,
    • Sleeps 10
      Book it Now!
      2 - 3 night minimum stay
      • 6 BR,
      • 7 BA,
      • Sleeps 14
        (7)
        30 night minimum stay
        • 2 BR,
        • 2 BA,
        • Sleeps 6
          (3)
          4 night minimum stay
          • 4 BR,
          • 3 BA,
          • 2 HF BA,
          • Sleeps 12
            (5)
            • 4 BR,
            • 3 BA,
            • Sleeps 7
              (4)
              14 night minimum stay
              • 3 BR,
              • 3 BA,
              • Sleeps 7
                (4)
                7 night minimum stay
                • 3 BR,
                • 2 BA,
                • Sleeps 6
                  (3)
                  $2,275 - $3,500
                  per week
                  Book it Now!
                  7 night minimum stay
                  • 3 BR,
                  • 2 BA,
                  • Sleeps 6
                    (3)
                    Book it Now!
                    2 night minimum stay
                    • 4 BR,
                    • 2 BA,
                    • 1 HF BA,
                    • Sleeps 8
                      2 Reviews
                      3 - 14 night minimum stay
                      • 3 BR,
                      • 2 BA,
                      • 1 HF BA,
                      • Sleeps 6
                        (7)
                        7 - 30 night minimum stay
                        • 3 BR,
                        • 2 BA,
                        • Sleeps 6
                          (3)
                          27 - 30 night minimum stay
                          • 4 BR,
                          • 3 BA,
                          • Sleeps 8
                            3 - 7 night minimum stay
                            • 5 BR,
                            • 4 BA,
                            • Sleeps 10
                              (4)
                              3 - 31 night minimum stay
                              • 4 BR,
                              • 3 BA,
                              • Sleeps 9
                                1 Review
                                30 - 31 night minimum stay
                                • 5 BR,
                                • 4 BA,
                                • 1 HF BA,
                                • Sleeps 6
                                  1 Review
                                  30 night minimum stay
                                  • 3 BR,
                                  • 3 BA,
                                  • Sleeps 8
                                    7 - 30 night minimum stay
                                    • 5 BR,
                                    • 3 BA,
                                    • 1 HF BA,
                                    • Sleeps 10
                                      2 - 7 night minimum stay
                                      • 2 BR,
                                      • 1 BA,
                                      • 1 HF BA,
                                      • Sleeps 6
                                        7 night minimum stay
                                        • 3 BR,
                                        • 3 BA,
                                        • Sleeps 8
                                          • 3 BR,
                                          • 1 BA,
                                          • 1 HF BA,
                                          • Sleeps 6
                                            1 Review
                                            17 more choices from the HomeAway Network
                                            Book it Now!
                                            • 4 BR,
                                            • 4 BA,
                                            • 1 HF BA,
                                            • Sleeps 10
                                              3 - 7 night minimum stay
                                              • 3 BR,
                                              • Sleeps 8
                                                2 Reviews
                                                $500
                                                per night
                                                3 - 31 night minimum stay
                                                • 5 BR,
                                                • 2 BA,
                                                • Sleeps 9
                                                  1 Review
                                                  $4,250 - $4,950
                                                  per week
                                                  7 night minimum stay
                                                  • 3 BR,
                                                  • 2 BA,
                                                  • Sleeps 6
                                                    (3)
                                                    2 - 3 night minimum stay
                                                    • 1 BR,
                                                    • 1 BA,
                                                    • Sleeps 15
                                                      2 Reviews
                                                      3 - 7 night minimum stay
                                                      • 4 BR,
                                                      • 3 BA,
                                                      • Sleeps 10
                                                        7 night minimum stay
                                                        • 5 BR,
                                                        • 4 BA,
                                                        • Sleeps 12
                                                          (4)
                                                          7 night minimum stay
                                                          • 5 BR,
                                                          • 2 BA,
                                                          • Sleeps 9
                                                            (3)
                                                            2 - 7 night minimum stay
                                                            • 3 BR,
                                                            • 2 BA,
                                                            • Sleeps 7
                                                              (3)
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                                                              Recent Shelter Island Reviews

                                                              Beautiful home, perfect vacation

                                                              5 of 5
                                                              My wife and I were lucky enough to find this home and spend our July out there. Could not have been a more perfect stay. Home is meticulously designed and decorated, an open sunny home during the day and a warm retreat at night. The garden and pool is a perfect oasis and a great place to forget about day to day life and relax. Shelter Island itself is serene and has everything you could want from a summer vacation. Beaches and boating and barbecues or a short trip to the hamptons and the ocean. Hoping to make it back again next summer!
                                                              • Submitted: Sep 9, 2014
                                                              • Stayed: Jul 2014

                                                              Heavenly!

                                                              5 of 5
                                                              This place is a true treasure. Incredibly comfortable home with everything we could need on hand. Ceiling fans in every room make the place so cool and breezy that we barely needed the a/c despite the heat. I've never rented a house before and went with very low expectations- brought my own towels, sheets, utensils, plates, and needed none of it as everything was clean and comfortable and lovely. The screened-in porch was a delight. My kids had a blast watching the deer in the early morning and early evening, and the tire swing was a HUGE bonus and total surprise! My daughter lost her mind with joy to discover that. and us grownups relished the hammock and the plentiful and very comfy chairs and sofas. The pool was perfect- my crew has little tolerance for cold water so the heater was fantastic and the hot tub another treat. The views of the massive and gorgeous property were spectacular and there were wonderful views from every room. I can't stop raving about this house and the property and the location was fantastic as well. Nothing was more than 5 minutes away. We fell in love with Whale's Tale for mini golf and I am still dreaming about Commander Cody's fried scallops. I grew up going to the Hamptons and had never been to Shelter Island and was thrilled to experience this treasure- beautiful and even on Labor Day weekend not a crowd or single incident of traffic to be found. Celina was extremely helpful, very responsive to questions and returned my security deposit within one day! Only thing to note is that the laundry and second bathroom are in the basement, and that was a bit tricky to find- it's the door in the screened in porch! I can't recommend this property enough and am already plotting my next stay here. Thank you so much, Celina and Tom for making our stay just glorious!
                                                              • Submitted: Sep 3, 2014
                                                              • Stayed: Aug 2014

                                                              Charming Cottage and Terrific Owners

                                                              5 of 5
                                                              We had a wonderful multi-week stay here. The house is as charming as advertised. We swam off the dock every day. Also kept my 20' sailboat at the dock and had great fun sailing in Gardner's bay. Topping it all off, the owners were a delight to deal with as we settled in and got our bearings. If you're considering this property give it a go, you'll be glad you did!
                                                              • Submitted: Aug 24, 2014
                                                              • Stayed: Jun 2014