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Shelter Island Vacation Rentals

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    Don't let other travelers get your favorite Shelter Island vacation rental. You're so close to securing your perfect getaway. Book today.
    All 27 Rentals in Shelter Island
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    >>> ROMANTIC Beach Getaway! Seclusion, Waterfalls1 / 20
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Sunshine Bungalow Shelter Island Retreat1 / 26
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Exquisite Waterfront Estate on Shelter Island NY; 100 Foot Dock; Beaches, Town1 / 14
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Outdoor Pool (Heated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a great summer retreat? Restaurants, antiquing, wineries, biking, canoeing, tennis, golf and of course the beach are all yours to be had at this charming east end gem on laid back Shelter Island. This renovated Country Cape is nestled on a spacious and lush ¾ acre wooded lot....
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    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is a water lover’s paradise on sheltered water with easy access to surrounding east end towns. “2 East” features over 1500 square feet of decks & porch on three levels overlooking West Neck Harbor, with an opportunity to be in sun or shade and still enjoy spectacular water views. There...
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    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Relax in this Spacious, Light-Filled Vacation Home in Coveted Silver Beach1 / 21
    (5)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Balcony
    • Parking
    • Terrace
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 6
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    Newly renovated! Quiet, private, short walk to the beach.1 / 23
    (19)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Patio
    • Air Conditioning
    • Internet Access
    • Washer
    • Grill
    • DVD Player
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Shelter Island Tree House -5 minute walk to Private Beach and Nature Preserve1 / 22
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Patio
    • Satellite TV
    • Parking
    • Air Conditioning
    • Washer
    • Internet Access
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Beachfront Home with Dock1 / 21
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Patio
    • Balcony
    • Satellite TV
    • Internet Access
    • Grill
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Waterfront 5 BR home With Stunning Water Views with 240 Foot Private Beach1 / 19
    (5)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Satellite TV
    • Grill
    • DVD Player
    • Washer
    • Patio
    • Parking
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Lovely Historic Restored Heights Victorian1 / 17
    (6)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • Washer
    • Grill
    • Housekeeping Included
    • Central Heating
    • Parking
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Art Loving Sailors'  Zen Retreat--Waterfront 5 Bedroom House1 / 24
    (5)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • DVD Player
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • Air Conditioning
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Modern Shelter Island CA Ranch with pool1 / 23
    (3)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Grill
    • Private Outdoor Pool (Unheated)
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Shelter Island Summer Home Rental1 / 20
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Grill
    • Balcony
    • Internet Access
    • Washer
    • DVD Player
    • Patio
    • Air Conditioning
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    Beautiful Contemporary Spacious Home on Shelter Island1 / 19
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Internet Access
    • DVD Player
    • Grill
    • Balcony
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Beautiful Secluded Family Home on Shelter Island.1 / 23
    (6)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Patio
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Air Conditioning
    • Grill
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Fabulous Shelter Island home w huge pool, steps to private Beach1 / 20
    (5)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Washer
    • Air Conditioning
    • Grill
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Beautiful, Waterfront Home With Dock And Heated Gunite Pool!1 / 24
    (13)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Washer
    • Air Conditioning
    • Satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Internet Access
    • Grill
    • Patio
    • Washer
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Parking
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!1 / 21
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Grill
    • Internet Access
    • Satellite TV
    • Private Outdoor Pool (Unheated)
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Newly Renovated Stylish and Charming  A-frame Home On Private Quiet Road1 / 24
    (12)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Air Conditioning
    • Parking
    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Satellite TV
    • Grill
    • DVD Player
    • Patio
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Grill
    • Washer
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 7
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Satellite TV
    • Internet Access
    • Housekeeping Included
    • Air Conditioning
    • Washer
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Lovely 3 Bedroom Home on Ice Pond1 / 6
    (4)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
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    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island Heights, Shelter Island 11965
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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