Vacation rentals in Shelter Island
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Top-rated vacation rentals in Shelter Island
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Shelter Island vacation rentals
Other great vacation rentals in Shelter Island
Guest favourite
Home in Shelter Island
4.92 out of 5 average rating, 73 reviewsFamily Friendly Island Home
Oct. 7 – 14
$999 CAD per night
Guest favourite
Home in Shelter Island
4.92 out of 5 average rating, 52 reviewsBeautiful beach home with pool & water views!
May 9 – 16
$1,057 CAD per night
Guest favourite
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
Jun. 28 – Jul. 5
$1,041 CAD per night
Guest favourite
Cottage in Shelter Island
4.88 out of 5 average rating, 16 reviewsWaterfront Getaway on Shelter Island
Nov. 18 – 25
$1,029 CAD per night
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
Sep. 13 – 20
$1,239 CAD per night
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
Nov. 8 – 15
$1,656 CAD per night
Superhost
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
Sep. 24 – Oct. 1
$716 CAD per night
Guest favourite
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
Mar. 27 – Apr. 3
$1,312 CAD per night
Quick stats about vacation 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
$165 CAD before taxes and fees
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- Kid-friendly rentals Shelter Island
- Rentals with a fireplace Shelter Island
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- Monthly Rentals Shelter Island
- Rentals with beach access Shelter Island
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- Pet-friendly rentals Shelter Island
- Rentals with a firepit Shelter Island
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- House rentals Shelter Island
- Family-friendly rentals Shelter Island
- Beachfront rentals Shelter Island
- Rentals with pools Shelter Island
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