Dappled Sunlight
8 guests
4 bedrooms
Northwest Harbor, East Hampton
Make like a New Yorker and escape to the famous Hamptons. This home has everything you could need for an effortless, laidback break from the city.
Shelter Island Luxury Rentals
We selected the 108 homes worth renting in this location
Home spotlights in Shelter Island
The Old Life-Saving Station
13 guests
6 bedrooms
East Marion, Southold
Anyone with a subscription to HBO might recognise The Old Life-Saving Station. The home has featured in both Lena Dunham’s Girls, and more recently, The Undoing, starring Hugh Grant and Nicole Kidman.
Light of Romance
14 guests
6 bedrooms
Springs, East Hampton
Find your own slice of heaven in East Hampton with a stay in this impressive glasshouse. Surrounded by lush trees with beautiful views, this is the perfect setting for a restorative retreat or special family gathering.
Marble Muse
8 guests
4 bedrooms
Water Mill, Southampton
It may look Old World from the outside, but behind this home's traditional shingle exterior is a luxurious and playful home to call your own in The Hamptons. Packed with designer touches, we love the bright, double-height living space, with its character fireplace and huge windows.
We selected the top 3% holiday homes in Shelter Island Luxury Rentals
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A handpicked selection of the best luxury homes in Shelter Island, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.
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