The Top 5

Top 5 Shelter Island Summer Rentals

Shelter Island is away from it all while still just a ferry ride from both the North and South forks. The island itself offers fun on the water, quaint shops and cafes, and the natural beauty of the Mashomack Preserve. Time is running out to secure a summer rental on Shelter Island. Here’s a quintet of vacation houses available from Memorial Day through Labor Day.

$110,000, Memorial Day to Labor Day Shelter Island
Heron Lane. $110,000 Memorial Day to Labor Day.

Sited on 1.1 waterfront acres, this 2,000-square-foot Modern has three bedrooms and four baths. It was recently renovated as a contemporary beach house, and it offers privacy while also being convenient to the South Ferry.


6 Club Drive. $110,000, Memorial Day to Labor Day
6 Club Drive. $110,000 Memorial Day to Labor Day

Located on Gardiners Bay with views of Mashomack Preserve, this 3,500-square-foot Contemporary with 4 bedrooms and 3.5 baths is sited on 1 acre. The ceiling is high, the fieldstone fireplace is massive, and there are windows all around the post-and-beam home.


Gardiners Bay Drive. Memorial Day to Labor Day, $125,000
Gardiners Bay Drive. $125,000 Memorial Day to Labor Day

This Beach House on 1 acre is 2,478 square feet with 3 bedrooms and 3 baths and 2 powder rooms. The property has mature trees, a large deck, a swimming pool and 125 feet of beachfront. Among the amenities are 2 fireplaces, central air conditioning and a seperate apartment above the garage. Views include the North Fork, Bug Light and Connecticut.


$150,000 Memorial Day to Labor Day
$150,000 Memorial Day to Labor Day

This 3.8-acre Compound includes a main house and a carriage house. The main residence has 3 bedrooms including a master ensuite with attached office, 2.5 baths, a living room, a dining room, a family room, a library, a sunrooms, a kitchen with 2 dishwashers, a Viking stove and central air conditioning. The carriage house has 3 bedrooms, 2,5 baths, a living/dining room, and a kitchen with dishwasher, The grounds include a pool.


Landing Lane. $175,000 Memorial Day to Labor Day
Landing Lane. $175,000 Memorial Day to Labor Day

This 6,500-square-foot Modern on 1.22 acres has 4 bedrooms and 6 baths. The residence was built in 2006 and includes all modern amenities. The fully finished basement includes a gym. The grounds have a kidney-shaped pool surrounded in brick plus a hot tub.

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