We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Shelter Island Vacation Rentals

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Price
    per night
    $1,128 Average
    |||
    |||
    $0$1,000+
    Suitability
    More filters
    Don't let other travelers get your favorite Shelter Island vacation rental. You're so close to securing your perfect getaway. Book today.
    All 6 Rentals in Shelter Island
    Sort by:
    Default
    ***WINTER SPECIAL: Long weekend or week for $999 plus utils. Oct 15-April 15.1 / 30
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    other travelers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Sunshine Bungalow Shelter Island Retreat1 / 26
    (1)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    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....
    View all property information
    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Inquiry
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Yard
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Cable/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...
    View all property information
    Location Information
    Shelter Island, Hamptons 11964
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
    Make Inquiry
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Hot Tub
    • Wi-Fi
    • Patio
    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,...
    View all property information
    Location Information
    Shelter Island Heights, Shelter Island 11965
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Inquiry
    Save time - get the best Shelter Island rentals sent straight to your email!
    Get the List
    Shelter Island Flight and Weather Info
    Low airfares recently found by TripAdvisor travelers
    |
    Local Weather
    Powered by Weather Underground
    40° 22°
    December
    33° 17°
    January
    35° 18°
    February
    40° 24°
    March

    Additional Shelter Island Info

    Go to map view
    • Local time: 04:59 AM (EST)
    List your property
    Owner log in