Shelter Island Luxury Rentals

We selected the 104 homes worth renting in this location

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Home spotlights in Shelter Island

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, North Fork

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.

Far Away Coast

Far Away Coast

  • 8 guests

  • 5 bedrooms

North Sea, Southampton

Traditional on the outside, smart and modern inside, this home is a serene coastal haven. Every element here has been carefully considered to ensure you feel as welcome and relaxed as possible.

A Faithful Friend

A Faithful Friend

  • 10 guests

  • 6 bedrooms

Water Mill, Southampton

This home is nearly a hundred years old, but in terms of its luxury and comfort, it might as well be brand new. Once you’ve had a flick through the photos, you won’t be surprised to find out that it’s been featured in many design magazines.


We selected the top 3% holiday homes in Shelter Island Luxury Rentals

Explore the 104 most perfect homes in our collection

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Most popular homes in Shelter Island

The NY Loft

The NY Loft

  • 6 guests

  • 3 bedrooms

Greenwich Village, Manhattan

Bowie & Friends

Bowie & Friends

  • 2 guests

  • 1 bedrooms

Williamsburg, Brooklyn

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Crop And Saddle

Crop And Saddle

  • 6 guests

  • 4 bedrooms

Washington, Litchfield

Light of Romance

Light of Romance

  • 14 guests

  • 6 bedrooms

Springs, East Hampton

The Gold Rush

The Gold Rush

  • 4 guests

  • 2 bedrooms

Tribeca, Manhattan

The Park View

The Park View

  • 6 guests

  • 3 bedrooms

Gramercy Park, Manhattan

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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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