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VRBO is part of the HomeAway family, the world leader in vacation rentals with over 950,000 listings. We offer the largest selection of properties for any travel occasion and every budget. We’re committed to helping families and friends find a perfect vacation rental to create unforgettable travel experiences together. Learn More

Shelter Island - 41 vacation rentals

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This property allows you to book online with a credit card. After submitting a reservation request, the owner or manager has 24 hours to accept, at which time your card will be charged and you will receive an email confirmation

Shelter Island Travel Tips

You Will Love Shelter Island Vacation Rentals

Shelter Island vacation rentals are so great, you will recommend them to friends for years after your visit to the area! From adorable shack-like cafes to charming mom n' pop restaurants, you will find unique establishments in Shelter Island that are unlike anything you have experienced before! Enjoy a day strolling along the waterfront, observing the native wildlife, or visit the Mashomack Preserve to see 2,100 acres of Nature Conservancy. Either way, you will be touched by the efforts of the locals to preserve the natural elegance and charm of their neighborhood.

Summer Homes in Shelter Island Couldn't Be More Lovely

Summer homes in Shelter Island are so lovely, they could not be improved upon. Enjoy great beaches like Sailors' Haven, for days of sunbathing and picnicking on the sand, or spend your days indoors. The great thing about Shelter Island summer homes is that you can relax, enjoy the privacy, and spend time working on your novel or catching up on letter writing. Take a day trip to Long Island for hip clubs, five star restaurants, and high-end shopping, or stroll through The Hamptons star watching for frequent visitors like Gwyneth Paltrow and Jerry Seinfeld.

House Rentals in The Hamptons Are Something You'll Never Forget

House rentals in The Hamptons are not just a place to live for a few weeks each summer, they're an experience that you will remember forever. Rub elbows with celebrities like Paul McCartney, or get away from the crowds and visit Dead Man's Hill on Corona Avenue. Go clamming on the beach, or pick raspberries inland. There are quaint activities to be done in Shelter Island, and all over The Hamptons, that will make you feel relaxed and happy. You will love your trip to The Hamptons, and always remember it as the place where you had the best peaches in the world!

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