$38,500 per month
91 Shore Rd, Shelter Island, NY 11964
A romantic and secluded summer getaway. Enjoy a front row seat to breathtaking and dramatic views of the Shelter Island Sound, Crescent (Sunset) Beach, Quinipet Sailing, North Ferry, Greenport, Southold and 4th of July fireworks. Conveniently just steps from Kissing Rock, Crescent Beach, The Pridwin Hotel (Spa and Restaurant), Sunset Beach (Restaurant and Nightlife), Shelter Island House
$195,000 per month
47L S Ferry Rd, Shelter Island, NY 11964
Rental is Available in 2026: MD-LD $195,000, June $50,000, July $85,000., Aug. $60,000. and Sept. $40,000. 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
Tina Marika Kaasik Daniel Gale Sothebys Intl Rlty
$115,000 per month
16 Little Ram Island Dr, Shelter Island, NY 11964
In one of the most sought after locations on Shelter Island, this original waterfront cottage has the most beautiful water views overlooking Coecles harbor to Gardiners Bay, with full sunlight from Sunrise to Sunset. This 4 bedroom 2 bath property sits at the end of a long winding driveway providing great privacy. There has been a new kitchen renovation now providing water views while cooking.
$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
$60,000 per month
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
$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
$30,000 per month
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
Copyright © 2025 CoStar Group
