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Shelter Island Rentals

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Shelter Island Rentals

353 Houses

Romantic Shelter Island Cottage w/2 Pools & a Pond

Shelter Island Heights cottage

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 28 minutes

Price per night from

$385

1 / 24

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

Shelter Island house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$296

1 / 30

Luxurious ‘Shelter Island Hideaway’ w/ Pool!

Shelter Island house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 28 minutes

Price per night from

$495

1 / 26

Waterfront Charmer on idyllic Shelter Island

Shelter Island house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$929

1 / 19

★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. 2 hours 45 minutes

Price per night from

$600

1 / 35

55 Shore

Shelter Island Heights villa

6 bedrooms / 5 bathrooms / sleeps 12

Responds fast! avg. 16 minutes

Price per night from

$4,000

1 / 49

Fabulous Beach Getaway

Shelter Island house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$651

1 / 24
Viewing 38 of 353
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