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Shelter Island rentals with pool
We found 1,482 rentals with pool — enter your dates for availability
Explore Shelter Island rentals with pools

Work and Play Special! Extended Stay Discount
Sleeps 10 · 5 bedrooms · 2+ bathrooms
10 out of 10
exceptional
(48 reviews)
Top rated rentals with pools - Shelter Island

Highly recommend
10 out of 10
exceptional
(38 reviews)
Excellent experience with home, location, and property owner
Jeffrey M.
Stayed June 2024
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- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
- More for lessMore space, more privacy, more amenities — more value