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

Shelter Island Vacation Rentals

Browse 758 available vacation homes and compared across 2 trusted partners

Anytime
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

House Shelter Island
Shelter Island Waterfront Home!
Book now
House Shelter Island
Waterfront Property on Shelter Island
Book now
House Shelter Island
Private heated pool and spacious yard. 5 minute walk to the beach.
Book now
House Shelter Island
House with patio, grill & private pool
Book now
House Shelter Island
House with barbeque & pool
Book now
House Shelter Island
Beautiful Sag Harbor Home with Pool and easy walk to private beach or downtown
Book now
Cabin Shelter Island
'The Gate House'on Beach front Estate with Dockage. Walk to Village.
Book now
Cabin Shelter Island
Cottage on Beach front Estate with Dockage .Walk to Village
Book now
House Shelter Island
Vacation home with private pool, grill & garden
Book now
Apartment Shelter Island
Holiday apartment with yard & patio
Book now
House Shelter Island
House with grill, garden & patio
Book now
House Shelter Island
Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI
Book now
House Shelter Island
Child-friendly beautiful house with patio, yard & BBQ | Pets are welcome
Book now
House Shelter Island
Fully equipped ample house with barbecue & patio
Book now
House Shelter Island
NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!
Book now

Top 15 most Recommended Vacation Rentals on Shelter Island

Discover your ideal Shelter Island vacation rental with real-time comparisons of 758 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

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 $350
per night
(70)
View deal
House Shelter Island
House ∙ 5 guests ∙ 3 bedrooms

167 m² House

Shelter Island, Suffolk County, New York, United States
Cozy house rental in North Fork accommodates 5 guests and features a charming fireplace for a warm and inviting atmosphere.
from $340
per night
(10)
View deal
House Shelter Island
House ∙ 8 guests ∙ 3 bedrooms

186 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in Sag Harbor accommodates 8 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $1,196
per night
(23)
View deal
House Shelter Island
House ∙ 12 guests ∙ 5 bedrooms

353 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in Sag Harbor accommodates 12 guests and features a private pool for a relaxing getaway.
from $2,376
per night
(65)
View deal
House Shelter Island
House ∙ 8 guests ∙ 5 bedrooms

465 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 relaxing getaway.
from $1,171
per night
(10)
View deal
House Shelter Island
House ∙ 6 guests ∙ 3 bedrooms

279 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island accommodates 6 guests and features a cozy fireplace for a comfortable stay.
from $335
per night
(22)
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

228 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island accommodates 8 guests and features a private pool for relaxation and fun.
from $831
per night
(43)
View deal
House Shelter Island
House ∙ 8 guests ∙ 4 bedrooms

260 m² House

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island Heights accommodates 8 guests and features a cozy fireplace for warm gatherings.
from $534
per night
(32)
View deal
House Shelter Island
8 guests ∙ 4 bedrooms

House

Shelter Island, Suffolk County, New York, United States
This house rental in Shelter Island Heights accommodates 8 guests and features a spacious yard for outdoor enjoyment.
from $794
per night
(8)
View deal

More travel options

image-tag