$15,000 per month
24 Worthy Way, Shelter Island, NY 11964
Property Id: 2474336Perfect summer rental. A 3BR, 2BA Ranch that has been recently renovated. Large backyard deck for outside dining, close to beaches. EV Level 2 charging outlet. Available July $15,000; August $16,000.
$20,000 per month
9 Johnston Rd, Shelter Island, NY 11964
Shelter Island 4 Bedroom Cottage with Gunite Pool and Hot TubAn enchanting mid-century cedar-shake ranch with a new heated Gunite pool, separate outdoor hot tub, outdoor shower, cedar deck, pea-gravel driveway, hammock, and propane bbq grill. Four bedrooms and two full baths. The house has a breezy nautical theme and a large record collection with great four-speaker sound and an upright
Isaac Halpern Brown Harris Stevens Hamptons
$10,000 per month
6 Crab Creek Rd, Shelter Island, NY 11964
Property Id: 2474324Many updates with great rental rates. Open floor plan, beautiful sunlit enclosed porch, entertaining deck overlooking quiet grassy yard, and outdoor shower to rinse off from coming from the sandy beach close by. There are 3BR, master with brand new bathroom, and an additional full bathroom, and finished basement. June $7,000; July $10,000; June-July $15,000. Short term
$30,000 per month
4 Glynn Dr, Shelter Island, NY 11964
This Shelter Island home is the kind of summer rental people wait all year to find-turnkey, stylish, and effortlessly comfortable. Recently renovated and designer-furnished, the home is ready for immediate enjoyment. Bright, sun-filled interiors and multiple inviting living spaces create an easy flow for summer living, whether it's slow mornings with coffee, afternoons by the pool, or relaxed
Joseph Van Asco Douglas Elliman Real Estate
$62,500 per month
4 Pandion Rd, Shelter Island, NY 11964
A stunning architectural jewel in Pandion, this freshly built, never-before-lived-in residence is both design-forward and deeply inspiring. Clad in arctic pine tongue-and-groove and corten steel, its twisted gable form captivates from every angle, while exterior decking invites you to soak in the surrounding natural beauty. The design/build owner's home draws inspiration from exposure to Frank
$8,700 per month
59 Peconic Ave, Shelter Island, NY 11964
Classic Cape Cod Retreat Near Shell BeachEnjoy summer on Shelter Island in this charming Cape Cod–style home with tranquil water views just across the street and easy access to one of the island’s most popular beaches. Located less than half a mile from Shell Beach, this 4-bedroom, 3-bath home is set in a friendly, sought-after summer community.The bright, open living and dining area
Debra Von Brook Binder Daniel Gale Sothebys Intl Rlty
$35,000 per month
56 N Cartwright Rd, Shelter Island, NY 11964
Welcome to your ultimate summer escape. Tucked away on 2 lush, private acres along the shimmering waters of Coecles Harbor, this fully renovated 1800s farmhouse offers the perfect blend of historic charm and modern luxury. With sweeping harbor views and timeless style, the home features 3 bedrooms, 1.5 baths, a private dock, and a flexible studio/gym space in a separate building. Enjoy al fresco
$50,000 per month
47L S Ferry Rd, Shelter Island, NY 11964
Rental is Available in 2026: June $40,000 July $50,000., Aug. $60,000. Sept. $40,000. Located in our beloved 2,350 acres of Mashomack Nature Preserve, there are a handful of residences. At the end of this long private road through this preserve, one can find this breathtaking newly constructed modern home with no details left behind. This expertly crafted home is loaded with premium amenities,
Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
$14,400 per month
12 Dogwood Ln, Shelter Island, NY 11964
Discover the perfect island getaway in this spacious 4-bedroom, 2-bathroom home tucked away on a large, serene lot. Surrounded by mature landscaping, the property features a generous front porch overlooking a peaceful pond—an ideal spot for morning coffee or sunset relaxation. Inside, the home offers a bright and inviting layout with a well-appointed kitchen complete with a center island, perfect
Mackenzie Needham Daniel Gale Sothebys Intl Rlty
$7,500 per month
42 N Menantic Rd, Shelter Island, NY 11964
Escape to Tranquility Base, a light-filled modern retreat where timeless mid-century style meets today’s elevated comforts. Thoughtfully renovated and expanded, this 4-bedroom, 2.5-bath home is surrounded by lush, landscaped grounds and designed for seamless indoor–outdoor living—thanks to five sliding glass doors that open to a heated gunite pool and expansive entertaining deck.Enjoy the
Jeanmarie Bay William Raveis New York LLC
$63,000 per month
4 Ivy Place, Shelter Island, NY 11964
Located in Hay Beach, this year round furnished rental is available and fully furnished. 3 bedrooms and 2 full baths is located in the beautiful area of Hay Beach, just 2 minutes from Gardiners Bay Country Club. Large living room with fireplace and sliders out to the large awning covered deck. Large loft area off the living room could serve as an office area of for overflow guests.
Sheri Winter Parker Corcoran
$75,000 per month
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
Shelter Island, NY, is a secluded 20-square-mile island community accessible only by ferry, located two hours from Manhattan. Known for its rocky peninsulas and serene environment, the island offers a peaceful lifestyle with a low crime rate compared to the national average. The island's single grocery store fosters a close-knit community where residents quickly get to know each other. Seasonal changes impact the island's pace, with many residents leaving after summer but increasingly staying longer due to remote work. Attractions include Sunset Beach for swimming and water sports, and the Mashomack Preserve, a 2,000-acre nature reserve with hiking trails and diverse wildlife. Golfers can enjoy the Shelter Island Country Club and Gardiner’s Bay Country Club, while boaters often join the Shelter Island Yacht Club. The island hosts an annual Arts & Crafts Fair and a 10K race, along with school plays at the highly rated Shelter Island School, which serves around 175 students with a low student-teacher ratio. Dining options are vibrant, especially in summer, with popular spots like Stars Café, Vine Street Café, and SALT Waterfront Bar & Grill. Shopping includes essentials like the IGA Supermarket and seasonal farmers markets. However, the island lacks a hospital, mail delivery, and garbage pickup, requiring residents to use post offices and manage their waste. The South Ferry connects Shelter Island to Long Island, facilitating access to New York City via a two-hour drive or the Long Island Rail Road. Homes on the island range from Colonials to modern styles, often with spacious yards, and start at around $1.3 million.
There are currently 13 homes available for rent in Shelter Island, NY. The median rent is $35,000 per month, with single-family homes renting at $32,500.
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