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Shelter Island Rentals

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Shelter Island Rentals

345 Houses

WATERFRONT Estate on Shelter Island. Fully Renovated. 100 Ft DOCK

Shelter Island house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$294

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Luxurious ‘Shelter Island Hideaway’ w/ Pool!

Shelter Island house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 38 minutes

Price per night from

$495

1 / 26

55 Shore

Shelter Island Heights villa

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 29 minutes

Price per night from

$4,000

1 / 49

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island Heights cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 38 minutes

Price per night from

$385

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★Available Labor Day Wknd★Low Rates Aug 17-18★Shelter Island Retreat★

Shelter Island Heights bungalow

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 1 hour 48 minutes

Price per night from

$593

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Waterfront Charmer on idyllic Shelter Island

Shelter Island house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$920

1 / 19

Fabulous Beach Getaway

Shelter Island house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$646

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