Shelter Island Vacation Rental Homes By Owner

Ram Island Drive Beautiful Waterview 4-Bedroom Home, Newly Renovated with Huge Rooftop Deck 4BR/3BA w/ stunning water views and a newly renovated rooftop deck,... Read More

Spacious ocean front, two story home located in peaceful neighborhood on West Neck Harbor. Home is perfect for large families. Both first and second floor have... Read More

Spacious entertainment, relax by the fireplace or relax in the closed porch , Private Beach on the corner of property. Enjoy the 18x36 saltwater heated pool …. 3... Read More

Beautifully Renovated 4Br/3b, Pool, Waterview, Beach, Vaulted Ceilings, A/C. Exterior features include wrap-around porch, two additional decks, open... Read More

You can walk to the beach from this attractive home that comfortably sleeps 7. Enjoy cocktails and outdoor dining on the second floor wrap around deck. The... Read More

Newly renovated, spacious, 4 bedroom, 3.5 bath house on 1.25 acres in the Hay Beach neighborhood of Shelter Island overlooking the private golf course. You’ll... Read More

This charming and newly renovated 3 bedroom, 2 bath ranch style home is located on a quiet street close to both Sunset and Shell beaches and within walking... Read More

This lovely 2 bedroom, 1 bath (plus an outside shower) renovated cottage located on a large lot in the center of Shelter Island is the perfect home base for your... Read More

Available by month as of Nov 1, 2021 Newly renovated house with a mix of antique furniture, modern appliances, grand piano, marble floors and working fireplace.... Read More

Brand new renovation of interior designer harbor-front home with dock. This very special property features amazing light and views of Dering Harbor. Sun all day... 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

This secluded three-bedroom, two bathroom Silver Beach ranch house is perfect for any season. Enjoy the pool, covered porch and walking distance beaches in the... Read More

Congdon's Point is a five bedroom, six and one-half bathroom private home that is surrounded by water, beach and nature preserve. Each bedroom features en suite... Read More

Work from home at this picturesque 1700’s farmhouse sits on 5 private acres with gorgeous specimen trees. It has heated salt water gunite pool and a pond with... 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

Shelter Island is a unique place with incredible natural landscapes and gorgeous sunsets! Once you get off the ferry, drive to the end of a private road to find... Read More

Large, centrally located, fully and recently renovated two-story home with super-fast wifi, extra-large 82” flat-screen TV and sound system in the living room,... Read More

Moonlit Manor Mid-Century Modern Retreat with expansive outdoor areas, life-sized chess in front yard, firepit, five-minute bike ride to Hay Beach 3BR/2BA -... 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

Huge 4 bedroom, 2 1/2 bathroom home on heavenly Shelter Island. Minutes to beach and town. Overlooks a tranquil pond. Large grounds and deck, Kawai grand piano.... Read More