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Shelter Island Vacation Rentals

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    $470 Average
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    All 29 Rentals in Shelter Island
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    Waterfront Estate-200 ft Harborfront, Dock1 / 14
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Sunshine Bungalow Shelter Island Retreat1 / 19
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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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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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    About this property
    Charming 4 Bed spacious Victorian home in the Heights - close to everything! Living area with fireplace and bay window lovely front porch, dining and kitchen. 4 beds, 1.5 baths and an outdoor shower. Enjoy all the island has to offer from this...
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    Shelter Island Heights, Shelter Island 11964
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Pet friendly
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    About this property
    Adorable renovated farmhouse close to Golf Club, Crescent Beach and the Heights. Formal living and dining rooms, kitchen with pantry and full bath. Second floor has three bedrooms and a bathroom. Lovely porch and...
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    Shelter Island, Hamptons 11968
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    ->HAMPTONS - Shelter Island 4+Bdrm Euro Beach Home1 / 30
    (10)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Hot Tub
    • Waterfront
    • Private Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed March 23, 2015
    My wife and I are very hard to please when it comes to travel and accommodation. However, Shelter Island Hideaway left us wanting more. The pergola, the décor, the pool, the...
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    About this property
    DURING THE PEAK MONTHS, THIS HOUSE IS ONLY AVAILABLE BY THE WEEK OR LONGER! Property was voted as Winner of Best of Citysearch!. Shelter Island Hideaway is amongst the best summer getaway Vacation destination. The most confusing part is deciding whether you treat yourself to a relaxing for a...
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    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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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
    (13)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Central Heating
    • Internet Access
    • Grill
    • Balcony
    • Parking
    • Patio
    • Washer
    • DVD Player
    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 / 24
    (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
    (2)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
    (4)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Balcony
    • Grill
    • Washer
    • Satellite TV
    • Air Conditioning
    • Patio
    • Terrace
    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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    Amenities & Details
    • 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
    (7)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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    Walk to Wades Beach!1 / 20
    (4)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
    (7)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
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    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
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    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
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    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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    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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    Sheltered And Secluded; Pet Friendly1 / 24
    (13)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Parking
    • Grill
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    NEWLY RENOVATED WITH POOL, HOT TUB, AND FIREPLACE!1 / 21
    (6)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
    (8)Excellent
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • 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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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Patio
    • Air Conditioning
    • Internet Access
    • Washer
    • Grill
    • Satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Newly renovated, family friendly spacious home w/ pool and room for entertaining1 / 19
    (9)Excellent
    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
    • Satellite TV
    • Internet Access
    • Air Conditioning
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    • Grill
    • Patio
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    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    Shelter Island, Hamptons 11965
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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