Shelter Island Vacation Rentals - HolidayHomes base64Hash Shelter Island Vacation Rentals - HolidayHomes

Shelter Island Vacation Rentals

Browse 655 available vacation homes and compared across 2 trusted partners

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Guests
Anytime
Guests

Top-Rated Vacation rentals on Shelter Island

Book the highest-rated Shelter Island vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

Apartment Shelter Island
Holiday apartment with yard & patio
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House Shelter Island
Vacation home with terrace, barbeque & private pool
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House Shelter Island
Perfect Summer Retreat in Sag Harbor - Walk to Beach
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House Shelter Island
Vacation home with grill & garden | Nature view
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House Shelter Island
Renovated and Spacious Summer Home with Water View on Picturesque Island.
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House Shelter Island
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
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Cabin Shelter Island
Cottage with garden, BBQ & terrace
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House Shelter Island
Fully equipped vacation home with private pool, patio & barbeque
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House Shelter Island
House with terrace & grill
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House Shelter Island
Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
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House Shelter Island
House with garden, patio & private pool
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House Shelter Island
House with private pool, garden & barbeque
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House Shelter Island
Family-oriented house with yard, barbeque & patio | Nature view | Close to the beach | Pets are welcome
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House Shelter Island
House with terrace, barbeque & garden
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House Shelter Island
Steps from Cedar Beach ! Tranquil Retreat in the Heart of Wine Country
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Top 15 most Recommended Vacation Rentals on Shelter Island

Discover your ideal Shelter Island vacation rental with real-time comparisons of 655 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

House Shelter Island
10 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
This house rental in Sag Harbor accommodates 10 guests and features a cozy fireplace.
from $218
per night
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House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

265 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island Heights accommodates 8 guests and features a private pool for a perfect getaway.
from $843
per night
(40)
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House Shelter Island
House ∙ 4 guests ∙ 2 bedrooms

102 m² House

Shelter Island, Suffolk County, New York, United States
Cozy house rental in North Fork accommodating 4 guests with a family-friendly kitchen and a spacious yard for outdoor fun.
from $269
per night
(54)
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Condo Shelter Island
6 guests ∙ 2 bedrooms

Condo

Shelter Island, Suffolk County, New York, United States
This North Fork condo accommodates 6 guests and features a spacious balcony perfect for relaxing and enjoying the views.
from $307
per night
(19)
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House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

204 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in North Fork accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $444
per night
(20)
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House Shelter Island
6 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
This house rental in North Haven accommodates 6 guests and features a family-friendly kitchen and a spacious yard.
from $490
per night
(1)
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Apartment Shelter Island
Apartment ∙ 5 guests ∙ 2 bedrooms

125 m² Apartment

Shelter Island, Suffolk County, New York, United States
This spacious apartment rental in Sag Harbor accommodates 5 and features a modern kitchen for convenient living.
from $355
per night
(69)
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House Shelter Island
House ∙ 6 guests ∙ 2 bedrooms

73 m² House

Shelter Island, Suffolk County, New York, United States
Charming house rental in North Fork for 6 guests featuring a spacious yard perfect for outdoor activities.
from $123
per night
(45)
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House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

195 m² House

Shelter Island, Suffolk County, New York, United States
This House rental in Shelter Island accommodates 6 guests and features a private pool for a relaxing getaway.
from $723
per night
(64)
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