Holiday rentals near Shelter Island
We found 3,293 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:21 Nov - 28 Nov
Image gallery for Panoramic Ocean Views, Private Heated Pool, Spa, and Waterslide!
9.8 out of 10 rating
Exceptional
(127 reviews)
Panoramic Ocean Views, Private Heated Pool, Spa, and Waterslide!
San Diego, CA
8% off
Price is NZ$17,375
NZ$2,482 per night
includes taxes & fees
Find spaces that suit your style
House
Condo/Apartment
Find properties near top attractions in Shelter Island
Map Attractions
Find the best place to stay - Shelter Island
Oceanfront WhiteWater Views-Private Pool & Hot Tub--Best Sunset Cliffs Views
Sleeps 22 · 6 bedrooms · 6 bathrooms
9.6 out of 10
exceptional
(83 reviews)
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