Shelter Island: Vacation Rental By Owner

Wake up smiling every morning in this sun-filled house. Spend days lounging and evenings grilling and dining around the 40 long pool. Relax inside on the... Read More

This home is available for the first time! You can walk to the beach from this attractive home that comfortably sleeps 7. Enjoy cocktails and outdoor dining on... Read More

This Shelter Island beach house has all the necessary ingredients for a fabulous year-round getaway. Located on a shy acre just outside the Village of Dering... Read More

This stunning waterfront Estate House is a quiet paradise nestled in 7 private acres of nature on the pristine Menantic Peninsula. Enjoy strolls along the water’s... Read More

Enjoy the best that Shelter Island can offer at this renovated 2 bedroom waterfront gem. Nestled on West Neck Bay, this one-of-a-kind home is just 20ft from the... Read More

The perfect Hampton's retreat awaits at 'Shelter Island Hideaway,' a beautiful 4-bedroom, 4-bathroom vacation rental home. The private estate has 3,000 square... Read More

For those seeking a peaceful, quiet, zen-like place to spend their vacation or honeymoon, 'The Shelter Island Hideaway Beach Vacation Cottage' is the home for... Read More

This property is extremely quiet and peaceful sitting on almost an acre of beautifully landscaped gardens and backing onto a serene nature preserve. It was... Read More

Located on Shelter Island, NY down a quiet lane within walking distance of Wades Beach and the Nature Conservancy's Mashomack preserve. This impeccably... Read More

Vacation house rental w/stunning views, private dock and beach. Located minutes from South Ferry on pristine Smith's Cove, bordering Mashomack Preserve and... Read More

Perfectly situated just past the Island Boatyard and Salt in a peaceful neighborhood surrounded by water on 3 sides. 4 town landings and beach access across the... Read More

Beautiful Shelter Island Heights property - convenient to all. Includes Heights Beach Club on Shelter Island Sound (gorgeous private beach, covered porch,... Read More

This mid-century modern home sits on over an acre of land overlooking a tranquil pond. Located in the Shorewood section of Shelter Island just steps from a... Read More

Walk to Beach from this Bright and Comfortable 3 Bedroom / 2 Bath Cottage. The open floor plan of the New Kitchen, Dining Room and Living Room is enjoyed by all... Read More

Located in a very exclusive, quaint village of Dering Harbor. The house is located directly on the water with incredible views and fantastic sunsets. The... Read More

This home is a water lover’s paradise on sheltered water with easy access to surrounding east end towns. “2 East” features over 1500 square feet of decks & porch... Read More

This is a magical house. It is surrounded by woods and a pond. The only sounds you hear are the birds and other animals, the wind in the trees. It is a one minute... Read More

Architecturally designed 1,800 sq. ft. contemporary home. Three bedrooms, two bathrooms. Situated on a quiet country road, one-half mile to Wade’s Beach.... Read More

Completely renovated and updated 1929 Sear's kit home with beautiful views to Peconic Bay. Swim, fish for dinner, windsurf, Kayak or just take in amazing view... Read More

Located right on beautiful West Neck Harbor with plenty of private beach and wonderful swimming, fishing, clamming and boating. Perfect for one or two families,... Read More