Houses for Rent in Shelter Island, NY

This beautifully renovated 4-bedroom, 2.5-bath home offers a stunning blend of mid-century style and modern comfort, spanning 2,800 sq ft. Enjoy seamless indoor-outdoor living with five sliding glass doors leading to a heated gunite pool and expansive deck. The gourmet kitchen features a granite island and Electrolux appliances, while the lower level includes a kitchenette and recreational space. Ideal for relaxation or entertaining, this retreat is just moments from beaches and local dining on Shelter Island.

This delightful 3-bedroom, 2-bath home in Hay Beach offers a perfect blend of comfort and style. A large living room with a cozy fireplace opens to an awning-covered deck, ideal for relaxation. The spacious loft provides a versatile space for an office or guest overflow, while the fully furnished interior ensures ease and convenience. Enjoy the tranquil surroundings just minutes from Gardiners Bay Country Club in this charming contemporary sanctuary, spanning 1,487 square feet.

Nestled in West Neck Harbor, this 4,600 sq ft waterfront home features a private dock with a boat and captain, a designer interior, and breathtaking harbor views. Enjoy a first-floor primary suite, an adjacent guest cottage, and luxurious outdoor living with a heated saltwater pool, spa, sauna, and sunset-facing deck. This masterfully designed retreat offers six bedrooms, three living spaces, and a seamless blend of elegance and leisure.

This stunning 4-bedroom, 4-bath home spans 3,100 sq ft and features a modern open-plan great room that seamlessly connects to the pool and expansive fenced garden. Enjoy the beautifully landscaped grounds from the rock garden patio and relax in the 20x40 heated pool. Conveniently located within walking distance to beaches and local cafe, it perfectly combines comfort with the allure of Shelter Island living.

This immaculate 4-bedroom, 3.5-bathroom home boasts over 2,700 sq ft of exquisite living space, perfect for tranquil getaways. Recently renovated and beautifully furnished, the property features a brand new heated gunite pool, set in one of the quietest neighborhoods. Enjoy the stunning design and tasteful decor that make this rental a magnificent choice for relaxation and entertainment. A true escape not to be missed!

Enjoy breathtaking panoramic water views and mesmerizing sunrises over Gardiner's Bay from every room in this luxurious 3,000 sq ft contemporary retreat. Featuring open-plan living spaces, a chef's kitchen, and an oversized primary suite with private deck. The outdoors delights with a waterside infinity pool, dining pavilion, and professionally landscaped gardens, making this an unforgettable waterfront sanctuary.