Shelter Island, New York

Vacation Rentals in Shelter Island, New York

Discover 11 vacation rental properties in Shelter Island. From 2 to 5 bedrooms. Average $623/night. 100% have pools.

11 verified listings Book securely on VRBO Prices updated March 2026

11 properties available

Cozy family cottage on Shelter Island

Cozy family cottage on Shelter Island

2 beds 1 bath
PoolA/CWiFiBalcony
$427/night
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Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool

Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool

4 beds 2 baths
PoolA/CWiFiBalcony
$812/night
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Contemporary near Wade's Beach - 10 min drive to Sunset Beach/Shelter Island Hts

Contemporary near Wade's Beach - 10 min drive to Sunset Beach/Shelter Island Hts

3 beds 2 baths
PoolA/CWiFiBalcony
$445/night
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Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve

Cozy Shelter Island Cottage, walk to beaches and Mashomack Preserve

3 beds 2 baths
PoolA/CWiFiBalcony
$427/night
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Waterfront House With Dock And Private Beach

Waterfront House With Dock And Private Beach

3 beds 1 bath
PoolA/CWiFiBalcony
$853/night
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Perfect Family Summer Vacation Home Close to beach 18x42 pool

Perfect Family Summer Vacation Home Close to beach 18x42 pool

3 beds 2 baths
PoolA/CWiFiBalcony
$598/night
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Lovely Shelter Island cottage with panoramic bay views, secluded, screened...

Lovely Shelter Island cottage with panoramic bay views, secluded, screened...

4 beds 2 baths
PoolA/CWiFiBalcony
$540/night
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Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

Work and Play Special! Extended Stay Discount at a hideaway with Stellar Wifi!

5 beds 2 baths
PoolA/CWiFiBalcony
$958/night
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Lovely home by the sea with dock and heated Gunite pool!

Lovely home by the sea with dock and heated Gunite pool!

4 beds 3 baths
PoolA/CWiFiBalcony
$643/night
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Silver Beach Hideaway: newly updated quiet cozy cottage - 4 min walk to beaches!

Silver Beach Hideaway: newly updated quiet cozy cottage - 4 min walk to beaches!

4 beds 2 baths
PoolA/CWiFiBalcony
$453/night
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Shelter Island Hidden Waterfront Gem

Shelter Island Hidden Waterfront Gem

3 beds 2 baths
PoolA/CWiFiBalcony
$704/night
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