Holiday rentals near Shelter Island
We found 3,276 holiday rentals — enter your dates for availability
Scroll through and discover holiday rentals within easy reach of Shelter Island that provide the perfect home base for your trip. Whether you're travelling with a group or just with your pet, holiday homes have the amenities that you need and want for your stay, which might include a hot tub and a washer and dryer. At the end of the day, you'll find a property to rent that has what everyone needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Shelter Island
Showing deals for:27 Feb - 6 Mar
Image gallery for Luxury 5 star resort like dream home new 2024 AC private pool spa close to beach
9.6 out of 10, Exceptional, (63 reviews)
Exceptional
(63 reviews)
Luxury 5 star resort like dream home new 2024 AC private pool spa close to beach
San Diego, CA
8% off
Price is AU$22,174
for 7 nights, 1 home
AU$3,168 per night
includes taxes & fees
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Find the best place to stay - Shelter Island
Location! Location! Location!
Sleeps 5 · 2 bedrooms · 2 bathrooms
9.8 out of 10
exceptional
(328 reviews)
Top rated rentals - Shelter Island
Great getaway spot
10 out of 10
exceptional
(280 reviews)
Cozy place to stay in a great location with everything you need. Having your own private gated parking is a big plus!
Isabelle R.
Stayed Sept 2024
Peace of mindOur Book with Confidence Guarantee gives you 24/7 support
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