Properties For Rent in Westmoreland, Town of Shelter Island

Beautiful 3BR, 2BA home perfect for families. Enjoy a fireplace, dining room, back deck, and swing set. Great for outdoor enthusiasts!

Summer rental home on Wades Beach. Features a pool, 2 master suites, 2 guest bedrooms, open kitchen, great room, and 2-car garage. Perfect for a getaway.

Grand 5-bedroom, 5.5-bathroom compound bordering parkland. Features include a gourmet kitchen, theater room, game room, heated pool with spa, putting green, guest house, and 4-car garage. Perfect for large families or those seeking luxurious amenities.

Charming 1885 Victorian home in Shelter Island Heights, offering 4 bedrooms, harbor views, multiple decks, outdoor dining area, boathouse, and proximity to amenities. Freshly updated and lovingly maintained.

Victorian home rental with high-end restoration. Features 4 bedrooms, an office, a finished lower level, and beautiful gardens. Close to beach club, tennis courts, and golf course. Perfect for those seeking a luxurious and private island getaway.

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.

Recently renovated ranch with sunny living room, new kitchen appliances, 3 bedrooms, and West Neck Bay views. Day dock access across the road. Sofa converts to queen-size bed. Ideal for a family or those seeking waterfront access.

Classic restored farmhouse on the harbor with updated kitchen and baths. Features a veranda, water views, brick fireplace, modern furnishings, and a shared pool. Three guest bedrooms and two full baths. Suitable for those seeking a tranquil waterfront retreat.

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.

Victorian Traditional home rental. Four bedrooms, two and a half baths, kitchen, breakfast room, dining room, and master suite. Two-week minimum rental.

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

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.