Rent Luxury Self-Catering Apartments in Shelter Island

We selected the 914 homes worth renting in this location

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Age 13+

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Children

Age 1 to 12

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Home spotlights in Shelter Island

Divine Inspiration

Divine Inspiration

  • 10 guests

  • 4 bedrooms

Great Barrington, Lee

There are a lot of adjectives we could throw at this home in The Berkshires; cosy, darling, divine. But none of them really do it justice.

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?

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.

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, New York

Wander Inn is an architect-renovated ranch in a beautiful setting. Built in the sixties, this home is made for relaxation and indulgence.


We selected the top 3% holiday homes in Shelter Island Self-Catering Apartments

Explore the 914 most perfect homes in our collection

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Most popular homes in Shelter Island

Painted Shadows

Painted Shadows

  • 6 guests

  • 3 bedrooms

Loudonville, Colonie

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Harbor Hymn

Harbor Hymn

  • 4 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

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Frequently asked questions

Book luxury Self-Catering Apartments in Shelter Island, and enjoy a memorable stay for all the right reasons. We leave no stone unturned in our pursuit of the most remarkable homes, vetting everything from shower pressure to design aesthetic. Every home in our collection of luxury Shelter Island Self-Catering Rentals comes fully furnished with a well-equipped kitchen, all linens, and essential bathroom toiletries included. And should you need any help in finding the perfect home, our friendly experts are always on hand to help.

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