With it's Caribbean flair, 3 waterfalls, 2 pools and 75' Koi pond, our Vacation home is possibly the most Romantic Hamptons Hideaway Vacation Cottage Home Rental...

Adorable waterfront cottage is located on Menantic Creek. Enjoy kayaking up Menantic or a short bike ride to Wade Beach. Perfect for families.

You will enjoy this family-friendly, spacious, and light-filled home featuring a mix of contemporary and traditional interior design, located in coveted Silver...

Exterior features include wrap-around porch, two additional decks, open landscaping, partial water views and two-car garage. The interior boasts an open floor plan...

This Shelter Island hideaway feels like a romantic French country house complete with fragrant lavender. It’s a newly renovated barn which has been converted with...

This house is located in the quiet and safe community of Hay Beach. Set back at the end of a 300 ft driveway, this country home is on 1 + acres of land in a scenic,...

Lovely three bedroom cottage centrally located. Cook's kitchen, cozy living room with fireplace, two bathrooms, southern light, and large, private yard.

At the end of a long driveway you’ll find this centrally located, tranquil and secluded country home. Surrounded only by trees, you’ll marvel at the how big the sky...

Stroll down a private road and just a stone's throw from a beach you will find this enchanted refuge tucked away among lush green moss and towering trees.

Private luxury Island Compound. Ultra clean and bright! Tastefully modern decor! Very quiet, private, peaceful location!!

2 bedrooms with queen sized beds, 1 bedroom with 2 twin beds, 3 outside porches with patio furniture, large country kitchen with double ovens, eat in dining room,...

Your summer getaway can be for a Week or longer! Enjoy one week or more, luxuriate for a Month or the entire Summer. Your stay will be comfortable and enjoyable in...

Bright and Comfortable 3 bedroom / 2 bath Summer Cottage. The open floor plan of the Kitchen, Dining Room and Living Room creates a great place from morning to...

This quaint island community is in the center of it all. Quiet setting with all the best amenities. Close to the Sag Harbor, Montauk and the North Fork's Wine...

Situated on one half acre of protected waterfront, this house has an open floor plan to entertain with ease and style. The gourmet kitchen includes a Viking stove...

Centrally located, with hot tub, walk to beaches, restaurants and golf courses, newly renovated 3 bedroom, 3 bath house. Situated on a full acre of land with...

Entertain your family and guest in this 6 bedroom home in quiet cul-de-sac area. Lounge by the pool or walk to beach. This house is immaculate.

10A Serpentine Drive is a newly built, very private residence in a wooded area on the highest point of Shelter Island Heights.

Spacious, contemporary and light-filled home, located in a quiet, safe, beach community, bordering the 2000+ acre Mashomack Wildlife Preserve.

Shelter Island is a hidden gem on the East End of Long Island, with calm waters protected by the North and South forks, making it a boaters paradise, with top...