Shelter Island Luxury Rentals

We selected the 108 homes worth renting in this location

Who's coming along?

Adults

Age 13+

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Children

Age 1 to 12

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Infants

Under 1

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Pets

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Home spotlights in Shelter Island

Dappled Sunlight

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.

The Old Life-Saving Station

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

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

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

Explore the 108 most perfect homes in our collection

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Most popular homes in Shelter Island

The Park View

The Park View

  • 6 guests

  • 3 bedrooms

Gramercy Park, Manhattan

The Quartet

The Quartet

  • 12 guests

  • 4 bedrooms

Lenox Hill, Manhattan

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Retreat to Nature

Retreat to Nature

  • 15 guests

  • 7 bedrooms

Jewett, New York

A Faithful Friend

A Faithful Friend

  • 10 guests

  • 6 bedrooms

Water Mill, Southampton

The Artful Eats

The Artful Eats

  • 9 guests

  • 4 bedrooms

Hell's Kitchen, Manhattan

Gramercy Garden

Gramercy Garden

  • 10 guests

  • 4 bedrooms

Gramercy Park, Manhattan

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Frequently asked questions

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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