Houses For Rent in Westmoreland, Town of Shelter Island

3 bed, 2 bath home on 1.5 acres with a pool and wisteria-covered pergola. Perfect for those seeking a relaxing retreat with outdoor space.

Beautiful home with many updates, open floor plan, enclosed porch, deck, outdoor shower, 3BR, 2 full bathrooms, and finished basement. Great for families or groups seeking a summer rental near the beach.

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

Bright contemporary home, 3 bedrooms, 2.5 baths, central AC. Open layout, entertainment deck, lower-level walkout deck. Two-week minimum rental. Perfect for a summer getaway!

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.

Elegant waterfront home on West Neck Bay, perfect for summer vacations. Features a spacious foyer, custom kitchen, multiple bedrooms with en-suite bathrooms, a large veranda, and a deep-water dock. Enjoy sunsets, breezes, and easy access to dining, beaches, and golf.

Freshly renovated Shelter Island Cape Cod with rocking chair veranda, expansive living spaces, open kitchen, multiple bedrooms and baths, outdoor entertainment deck, and deeded easement on Menantic Creek. Perfect for summer getaways!

Remodeled waterfront home in Hilo Shores with 4 bedrooms, 3.5 baths, and a pool. Features a deep water dock, perfect for summer rentals.

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.

Charming renovated Victorian home on 1.44 acres in Dering Harbor. Features a screened porch, updated kitchen, 5 bedrooms, a pool, and a deep-water dock. Ideal for families or those seeking a tranquil retreat.

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.

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.

Spacious 5-bedroom home with bonus room, gunite pool, near kayak landing and sandy beach. Available for summer rental with additional September rental possible.

Modernist home built in 2017, offering stunning views of a 9-acre preserve. Features an open layout, high-end kitchen appliances, primary en-suite bedroom, and convenient mini sleeping bunks. Located near a marina and two beaches. Ideal for summer rentals.

Recently renovated sun-filled farmhouse with open floor plan, gourmet kitchen, and outdoor deck. Close to Coecles Harbor Marina. Ideal for boaters and families.

6-bedroom 3.5-bathroom home available for summer rental. Features an open floor plan, floor-to-ceiling windows, and a spacious pool. Perfect for a summer getaway!

Sleek modernist home near the marina, featuring a pool, high-end architecture, and harbor access. Perfect for those seeking a luxurious, stylish escape. Two-week minimum rental.

Contemporary home in Conservancy Estates, Shelter Island. Open floor plan, fireplace, media room, primary en-suite bedroom, 2 guest bedrooms, pool, deck, close to ferry and beach. Perfect summer getaway!

Charming 2-bedroom, 2-bath cottage in Shelter Island's Montclair Colony. Enjoy a living room with convertible sofa, separate dining area, kitchen, and enclosed porch. Conveniently located near beaches, restaurants, and the marina. Perfect for couples or small families seeking a relaxing getaway.

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.