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Shelter Island Vacation Rentals

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    $1,137 Average
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    All 7 Rentals in Shelter Island
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    WATERFRONT Estate on Shelter Island. Fully Renovated. 100 Ft DOCK1 / 30
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    3 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
    • Cable/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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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Hot Tub
    • Patio
    • Terrace
    • Wi-Fi
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    55 Shore is a spectacular waterfront villa on Shelter Island, just a short walk from Sunset Beach and its stylish hotel. Enjoying panoramic bay and sunset views and a private beach with two boat docks, the 7,500 square-foot villa features beautiful alfresco living areas, exquisite interior spaces,...
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    Location Information
    Shelter Island Heights, Shelter Island 11965
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Wi-Fi
    • Patio
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The perfect Hampton's retreat awaits at 'Shelter Island Hideaway,' a beautiful 4-bedroom, 4-bathroom vacation rental home. The private estate has 3,000 square feet of indoor space and luxurious accommodations for up to 9-10 guests. Enjoy the spacious pool, lounge around in the 1,500 square feet of...
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    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Patio
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Terrace
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    For those seeking a peaceful, quiet, zen-like place to spend their vacation or honeymoon, 'The Shelter Island Hideaway Beach Vacation Cottage' is the home for you. The luxurious, waterfront 2-bedroom, 1-bathroom vacation rental cottage offers 1,125 square feet of sheer Caribbean-style elegance....
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    Location Information
    Shelter Island Heights, Shelter Island 11964
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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