Book Luxury Short Stay Rentals in Shelter Island

We selected the 902 homes worth renting in this location

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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

The Mortar & Pestle

The Mortar & Pestle

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

The Mortar & Pestle takes its name quite literally from the mortar and pestle collection in the dining room, a detail that represents the character and charm of this home. The many indoor and outdoor social spaces cater to groups of friends and families who love home-cooked meals and value one another's company.

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

For the ultimate Montauk escape with style and character in abundance, this fisherman's cottage has you covered. Flamingo-pink shutters and the front door set the scene for a stay that's thoughtfully stylish, charming and quirky – a blend of boho and rustic that's sophisticated and easy to love.

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Look out for artists, poets and musicians in the area around this home – it’s located in Springs, arguably the coolest town in the Hamptons. In the past, it’s played host to visionaries like Jackson Pollock and Lee Krasner, Willem de Kooning, Kurt Vonnegut, and John Steinbeck.

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Escape the frenetic pace of daily life and revel in an unmissable opportunity to relax and recharge at this stunning Shelter Island getaway. Set on a quiet tree-lined street and just a ten-minute walk from the pebble-strewn seashore, the home is perfectly set up for family holidays and weekend retreats with friends.


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

Explore the 902 most perfect homes in our collection

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Most popular homes in Shelter Island

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Lake of Beauty

Lake of Beauty

  • 8 guests

  • 4 bedrooms

Columbia County, Livingston

Hitchbrook

Hitchbrook

  • 6 guests

  • 3 bedrooms

Sharon, Litchfield County

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Jewel on the Hudson

Jewel on the Hudson

  • 12 guests

  • 5 bedrooms

Coxsackie, New York

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Check upcoming rates & availability for Shelter Island Short Stay Rentals


Frequently asked questions

Browse our curated collection of Short Stay Rentals in Shelter Island. From impeccable interior design and chef-worthy kitchens, to fully furnished bathrooms and the inclusion of all linens, the homes in our collection come complete with everything you need. Each of the Shelter Island luxury short stay apartments in our collection has been expertly reviewed to ensure the quality standards you can trust, so book today to enjoy a getaway to remember. And should you need any assistance, our friendly team of experts are here to help you find the perfect home.

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