Holiday houses 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
Cottage in Shelter Island
4.96 out of 5 average rating, 90 reviews3 Bedroom Cottage Gem
15 – 22 July
$8,145 AUD total
Guest favourite
Cottage in Shelter Island
4.88 out of 5 average rating, 16 reviewsWaterfront Getaway on Shelter Island
24 Nov – 1 Dec
$8,054 AUD total
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 10 reviewsSpacious house with pool.
19 – 26 Sept
$9,696 AUD total
Guest favourite
Home in Shelter Island
5.0 out of 5 average rating, 16 reviewsFamily Friendly Oasis Steps to Water - Heated Pool
8 – 15 May
$12,954 AUD total
Guest favourite
Home in Shelter Island
4.97 out of 5 average rating, 76 reviewsModern, spacious SI home with pool
6 – 13 Feb
$10,260 AUD total
Guest favourite
Cottage in Sag Harbor
5.0 out of 5 average rating, 29 reviewsLuxury Gem At The Heart of Sag Harbor Village
24 June – 1 July
$9,763 AUD total
Superhost
Home in Shelter Island
4.88 out of 5 average rating, 69 reviewsCharming 4BR Cottage on Shelter Island
4 – 11 Sept
$5,924 AUD total
Guest favourite
Cottage in East Hampton
5.0 out of 5 average rating, 30 reviewsStorybook Cottage Seconds to East Hampton Village
23 – 30 Oct
$6,104 AUD total
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
$185 AUD before taxes and fees
Destinations to explore
- New City Accommodation & holiday rentals
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- Beachfront rentals Shelter Island
- Rentals with pools Shelter Island
- Rentals with outdoor seating Shelter Island
- Rentals with a fire pit Shelter Island
- Rentals with a patio Shelter Island
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- Pet-friendly rentals Shelter Island
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- House rentals Shelter Island
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- Rentals with a washing machine and dryer Shelter Island
- Fitness-friendly rentals Shelter Island
- Rentals with beach access Shelter Island
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