Monthly Rentals in Shelter Island Heights

Had a wonderful stay at Edward and Tracey’s place! Incredible lot and view of the water. Dock has a floating portion to ease access during low/high tide. Very private, nice quiet and secluded location. But also quite close to IGA (grocery), activities, and other local points of interest. House has lots of charm and had everything we needed for a multi-week stay. A great home base for your shelter island adventures! Thank you Edward and Tracey for your amazing hospitality! Would not hesitate to return to this special place.

We really needed the solitude and my daughter and I had a fantastic rest. What a great place to hibernate in the winter! Great comfortable beds, well stocked kitchen In a beautiful space. It is a bird sanctuary with nice walks and brilliant cycling.

Donna's apartment was extremely comfortable and in a perfect location to explore Sag Harbor and the rest of the Hamptons. This was exactly what my wife and I were looking for in order to accommodate us and our baby daughter. The apartment was as advertised, and Donna was extremely communicative throughout our week. Check in and check out were a breeze. I would absolutely recommend Donna's place.

It’s rare for an Airbnb to exceed expectations, but Jennifer’s place truly did. This was, without a doubt, the best Airbnb I’ve ever stayed in. The home features modern finishes, thoughtful furnishings, and more than enough space to comfortably accommodate a large group. It was spotless, well-organized, and free of unnecessary clutter. The location is ideal — just a short walk through quiet neighborhoods to reach anywhere in Greenport. Compared to local hotels, this property is an exceptional value at a fraction of the cost. For families traveling with children, the bunk room and a well-stocked closet full of toys were a wonderful bonus that helped keep the little ones entertained. 10/10 would recommend!