Search Vacation Homes in Shelter Island

"We have been coming back to the same house ... truly nice for a family/friend gatherings."

"Ok, if you are considering staying here, place is big and nice open concept. Two big refridgerators and kitchen dining room are lovely. Pool tables felt is very dirty and cues are down to wood. Outside pool is cracked and leaking so hose water needs to be constantly running making water cold. Deck has many soft spots and a couple of holes. Not like picture...no plants and outdoor furniture moldy....would not sit on love seat area. No one did. Needs a good bleaching. Great to have a washer and...

"Amazing house on the beach with tons of space for fun!!! We loved being right on the water. The kids found crabs and fished with some of the locals. Would definitely rent this place again!!"

"What a great vacation! This is an incredible, updated, very clean house with an amazing location within walking distance (or short drive) to a private beach. We appreciated all the amenities that came with the house: beach chairs, beach towels, outdoor furniture, hammock, smart TV, very comfortable beds, I could go on and on! The house is spacious and there is plenty of space to spread out. Howard the owner was extremely responsive to any questions, and also reached out before the trip and...

"Yard well maintained. Kitchen is beautiful. Very spacious. Nice size outdoor pool. Close to many activities like the wineries and shopping. Very nice neighborhood. The host reached out to me over our time there making sure everything was going well and if we needed anything."

"We booked late in summer and spent 2 nights on beach road when we should have stayed longer. Fantastic location, great neighborhood, clean and comfortable beach house, my wife and I very much enjoyed the house and the shore. Can’t wait to book again!"

"This cottage was so lovely and so close to parks and beaches! The neighborhood is quiet and everyone was so welcoming and friendly. Thank you so much to the owners! We had a great time!😊"

"Beautiful home in great location. Worked perfectly for our family. House was in amazing shape, outdoor patio was awesome! As prior reviews have said, make sure you have water shoes, the water for the first 5-10 ft is very rocky. But overall everything was amazing"