Holiday rentals in Shelter Island
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Top-rated holiday rentals in Shelter Island
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Shelter Island holiday rentals
Other great holiday rentals in Shelter Island
Guest favourite
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
22–29 Sep
$1,310 SGD per night
Guest favourite
Cottage in Shelter Island
4.88 out of 5 average rating, 16 reviewsWaterfront Getaway on Shelter Island
25 Nov – 2 Dec
$1,004 SGD per night
Guest favourite
Cottage in East Hampton
5.0 out of 5 average rating, 20 reviewsChic cottage on lush, secluded acre by the beach.
8–15 Dec
$458 SGD per night
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
20–27 Sep
$1,192 SGD per night
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
18–25 Mar
$1,597 SGD per night
Guest favourite
Cottage in East Hampton
5.0 out of 5 average rating, 30 reviewsStorybook Cottage Seconds to East Hampton Village
23–30 Oct
$758 SGD per night
Guest favourite
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
10–17 Jan
$1,293 SGD per night
Guest favourite
Cottage in Sag Harbor
5.0 out of 5 average rating, 29 reviewsLuxury Gem At The Heart of Sag Harbor Village
24 Jun – 1 Jul
$1,221 SGD per night
Quick stats about holiday rentals in Shelter Island
Total rentals
140 properties
Rentals with a pool
50 properties have a pool
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
100 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$163 SGD before taxes and fees
Destinations to explore
- New City Holiday rentals
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- Rentals with pools Shelter Island
- Rentals with a firepit Shelter Island
- Family-friendly rentals Shelter Island
- Family-friendly rentals Shelter Island
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- Rentals with a washing machine and dryer Shelter Island
- Rentals with a fireplace Shelter Island
- Rentals with a patio Shelter Island
- Beachfront rentals Shelter Island
- Rentals with beach access Shelter Island
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- House rentals Shelter Island
- Pet-friendly rentals Shelter Island
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