Vacation rentals near Shelter Island

We found 1,268 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals near Shelter Island that provide the perfect home base for your trip. Whether you're traveling with a group or just with your pet, vacation homes have the best amenities for spending time at your vacation home, including parking and a TV. No matter what you're looking for, you'll be able to choose a rental for everyone's needs, including a place that is accessible or non-smoking.

Vacation rentals with weekly discounts - Shelter Island

Showing deals for:Nov 7 - Nov 14
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more
  • More for less

    More space, more privacy, more amenities — more value