Houses For Rent in Gardiners Bay Drive, Town of Shelter Island

5 bedroom, 3 bath contemporary home with water views, perfect for summer rentals. Two-week minimum stay. Additional weeks may be available.

Tranquil waterfront oasis with breathtaking panoramic water views. Features an open plan den/media room, chef's kitchen, expansive decks, infinity pool, multiple porches, and a meticulously landscaped garden. Ideal for those seeking luxury and serenity.

Beachfront home with pool, offering breathtaking views of the lighthouse. Features include a spacious layout, multiple fireplaces, gourmet kitchen, and expansive lower level. Ideal for families seeking a luxurious coastal escape.

Luxurious 4-bedroom, 4-bath modern home near the beach. Chef's kitchen, spa-like master suite, heated pool, and golf course access. Perfect for a summer vacation rental.

Cheerful waterfront home with open plan living, dining, and updated kitchen. Features a waterside deck, great room, master suite with screened porch, and three additional bedrooms. Amazing beach access and dock. Two-week minimum rental.

Sleek, sun-filled modern home on ~1 acre bordering golf course with bay views. New kitchen, baths, pool. Open layout, media room, 1st floor bedroom with jack-and-jill bath, primary bedroom with spa bath. Close to 5 beaches. Perfect for families seeking a luxurious coastal escape.