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

Shelter Island Vacation Rentals

Browse 745 available vacation homes from 1 partner

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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

We use AI to generate the short summary in each offer below, check full description before booking.
Cabin Shelter Island

'The Gate House'on Beach front Estate with Dockage. Walk to Village.

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Cabin Shelter Island

Cottage on Beach front Estate Walk to Village

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Apartment Shelter Island

Holiday apartment with yard & patio

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House Shelter Island

House with grill, garden & patio

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House Shelter Island

Vacation home with patio, grill & yard

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House Shelter Island

Pleasant house | Pet-friendly

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House Shelter Island

Perfect Summer Retreat in Sag Harbor - Walk to Beach

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House Shelter Island

NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!

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House Shelter Island

Bright and Spacious Summer Home Steps from the Beach

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House Shelter Island

House with terrace & grill

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House Shelter Island

House with yard, private pool & terrace

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House Shelter Island

House with garden, patio & private pool

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House Shelter Island

House with grill, yard & private pool

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House Shelter Island

Vacation home with private pool, barbeque & patio | Perfect for remote work

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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 745 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

Family-friendly vacation home with private pool, yard & patio

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island accommodates 8 guests and features a private pool for a relaxing getaway.
from $837
per night
(50)
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

Vacation home with yard, hot tub & patio | City view | Perfect for remote work

Shelter Island, Suffolk County, New York, United States
This charming house rental in Sag Harbor accommodates 6 guests and features a cozy fireplace for a relaxing stay.
from $689
per night
(48)
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House Shelter Island
House ∙ 7 guests ∙ 4 bedrooms

Child-friendly lovely vacation home with garden, private pool & grill | Nature view | Perfect for remote work

Shelter Island, Suffolk County, New York, United States
Spacious house rental in Shelter Island Heights accommodates 7 guests and features a private pool for relaxation and fun.
from $1,068
per night
(21)
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House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

House with private pool & terrace

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 $357
per night
(1)
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with barbeque, terrace & garden | Perfect for remote work

Shelter Island, Suffolk County, New York, United States
This house rental in North Fork accommodates 8 guests and features a spacious yard for outdoor activities.
from $412
per night
(15)
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House Shelter Island
House ∙ 5 guests ∙ 3 bedrooms

Vacation home with barbecue, garden & patio | City view

Shelter Island, Suffolk County, New York, United States
This house rental in North Fork accommodates 5 guests and features a family-friendly kitchen perfect for gatherings.
from $562
per night
(72)
View deal
House Shelter Island
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with private pool & BBQ | Good for workation

Shelter Island, Suffolk County, New York, United States
This spacious house rental in Shelter Island Heights accommodates 10 guests and features a private pool for a relaxing getaway.
from $519
per night
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with private pool, terrace & barbeque | Nature view | Perfect for remote work

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island Heights accommodates 8 guests and features a private pool for relaxation and enjoyment.
from $1,094
per night
(8)
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

Vacation home with terrace, hot tub & grill | Perfect for remote work

Shelter Island, Suffolk County, New York, United States
This house rental in North Fork accommodates 8 guests and features a private pool for a relaxing getaway.
from $867
per night
(16)
View deal

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