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 NZ$25,439
for 7 nights, 1 home
NZ$3,634 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Find properties near top attractions in Shelter Island
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Find the best place to stay - Shelter Island
Showing deals for: 26 Feb - 1 Mar
Beach Suite at San Diego Shelter
Sleeps 6 · 1 bedroom · 1 bathroom
The current price is NZ$2,251
for 3 nights, 1 room
NZ$750 per night
includes taxes & fees
Top rated rentals - Shelter Island

our stay at La Jolla
10 out of 10
exceptional
(377 reviews)
We were very impressed with this place, it was perfect for us, a family of 4. We had everything we needed at the cottage and the bikes were perfect for us to cruise around.
Great hosts. We loved it.
The location was the best at walking distance from the beach.
We would love to go back and stay there.
Paulina W.
Stayed Jul 2022
- 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





























