Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Barn
Cottage
Estate
Hotel
House
Apartment
Boat
Bungalow
Cabin
Castle
Chalet
Condo
Farmhouse
Lodge
Studio
Townhome
Villa
Yacht

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Shelter Island Beach Vacation Rentals Vacation Rentals(38)

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

                                                              Recent Shelter Island Reviews

                                                              Fantastic, Family Friendly, Well-Equipped Dream

                                                              5 of 5
                                                              This house was wonderful. The kitchen was fully equipped with spices, paper goods, sunscreen, bug spray -- everything you need but don't necessarily want to pack. The pool and hot tub were the focal attraction for our clan, but the screened in porch and ample supply of board games were very much appreciated. My girls loved the family of deer who visited twice daily, and the close proximity to town and beaches was also a hit. The owners are incredibly responsive and helpful. I cannot say enough good things about this place! I would only add: the Clam Chowder at SALT is the best on the island!
                                                              • Submitted: Aug 18, 2014
                                                              • Stayed: Aug 2014

                                                              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

                                                              Shelter Island perfection

                                                              5 of 5
                                                              This is the most beautiful and meticulously built home I've ever rented in Shelter Island. Was a complete joy to vacation there.
                                                              • Submitted: Mar 31, 2014
                                                              • Stayed: Jul 2013