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Shelter Island Houses for Rent

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  • /31

    $90,000 per month

    • 3 Beds
    • 3 Baths
    • House for Rent

    23 Tuthill Dr, Shelter Island, NY 11964

    This newly updated ranch house on Tuthill Drive (a private road on Big Ram Island) has been reimagined with the greatest attention to detail and quality. The open plan connects a spacious sun and (high fidelity) TV room with living room (and wet bar),cook's kitchen, and full dining room Three bedrooms include a private guest suite (with steam shower)primary and secondary bedrooms both

    23 Tuthill Dr, Shelter Island, NY 11964
  • /11

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,512 Sq Ft
    • House for Rent

    3 Saint Johns St, Shelter Island Heights, NY 11965

    Set on a peaceful street in Shelter Island’s historic Heights neighborhood, this mid-century modern home has everything you need for an easy, laid-back summer. There’s plenty of room to spread out, a spacious deck for lounging or dining outside, and a gas grill ready for summer cookouts. You’re just a few blocks from shops, restaurants, and all the local action. As a bonus, you’ll have access to

    Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty

    3 Saint Johns St, Shelter Island Heights, NY 11965
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    $25,000 per month

    • 3 Beds
    • 2 Baths
    • House for Rent

    21 Peconic Ave, Shelter Island, NY 11964

    Discover summer on Shelter Island in this newly renovated and beautifully furnished 3 bedroom two bath cottage, with wrap around decks overlooking Peconic Bay and evening Sunsets. Located in this quiet community with Beaches directly across from your house this is Summer as you remember it. The open floor plan of the house provides great spaces for family and friends to enjoy meals and gather

    21 Peconic Ave, Shelter Island, NY 11964
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    $30,000 per month

    • 4 Beds
    • 4 Baths
    • 3,100 Sq Ft
    • House for Rent

    15 S Cartwright Rd, Shelter Island, NY 11964

    Located on the southern side of Shelter Island within close proximity to beaches and boating, this house has been completely renovated with all modern amenities in place. The entry porch leads you into the great room, which includes the kitchen, dining, living and lounge area. The kitchen and dining area are open plan and lead out to the pool, garden and expansive fenced garden. The bedrooms are

    Michael Brennan Douglas Elliman Real Estate

    15 S Cartwright Rd, Shelter Island, NY 11964
  • /20

    $45,000 per month

    • 4 Beds
    • 5 Baths
    • House for Rent

    20 Sunshine Rd, Shelter Island, NY 11964

    What a great place for a summer vacation! This stunning home is located on a beautifully landscaped, very private, .92 fenced and gated acre within easy distance of Wades Beach, Fresh Pond, library, and restaurants. That is if you can tear yourself away from the comforts of home. A covered front porch opens to a great room with living and dining areas, fireplace and glass doors to the back deck

    20 Sunshine Rd, Shelter Island, NY 11964
  • /27

    $50,000 per month

    • 3 Beds
    • 3 Baths
    • 3,000 Sq Ft
    • House for Rent

    28 Gardiners Bay Dr, Shelter Island Heights, NY 11965

    Experience the ultimate in tranquility and luxury at this secluded oasis, where every moment is a picturesque escape. Discover breathtaking panoramic water views and soak in the mesmerizing sunrise & sunsets over Gardiner's Bay from just about every room in the house. Boasting an impressive layout featuring an open plan den/media room, dining room, and chef's kitchen-all thoughtfully designed to

    Michael Brennan Douglas Elliman Real Estate

    28 Gardiners Bay Dr, Shelter Island Heights, NY 11965
  • /25

    $25,000 per month

    • 3 Beds
    • 3 Baths
    • 1,675 Sq Ft
    • House for Rent

    5 Bay Ave, Shelter Island, NY 11964

    Open plan beach house with superb water views located in the highly sought after Montclair Colony. Centrally located near markets and many conveniences, there is much to adore in this home. Open plan living room with sunroom, dining and eat in kitchen. This home offers two bedrooms with two full baths and another bedroom with a full bath over the two car garage. In addition the master bedroom has

    Michael Brennan Douglas Elliman Real Estate

    5 Bay Ave, Shelter Island, NY 11964
  • /35

    $75,000 per month

    • 6 Beds
    • 4.5 Baths
    • 4,600 Sq Ft
    • House for Rent

    15 Montclair Ave, Shelter Island, NY 11964

    Enjoy all The Hamptons have to offer in this newly recreated waterfront home in the heart of West Neck Harbor! Complete with a boat and complimentary captain at the end of your private dock. Every detail was masterfully thought through by a leading design team. The floor plan offers a first-floor primary suite, four additional private guest bedrooms with two gracious common living spaces, a

    Margot Reutter Corcoran

    15 Montclair Ave, Shelter Island, NY 11964
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