Shelter Island Homes for Five People

We selected the 376 homes worth renting in this location

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

0

Pets

An extra fee may apply

0

Home spotlights in Shelter Island

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.

Swan's Nest

Swan's Nest

  • 7 guests

  • 4 bedrooms

Bridgehampton, Southampton

You don't even need to step out of this home to take in the view of Sam’s Creek and Mecox Bay, with the sea stretching out in the distance. At this cottage by the water, built up on stilts, you’ll be able to watch it all from the comfort of home.

Venus In Furs

Venus In Furs

  • 6 guests

  • 3 bedrooms

Hudson, Columbia County

A grand townhouse in the middle of Hudson, Venus In Furs is not only a great place for exploring the Catskills and the Hudson Valley, but it’s also a destination in its own right. Whether sinking into the plush Chesterfield, or spending long evenings around the fire pit, you have plenty of options when it comes to relaxation.

The Pond House

The Pond House

  • 5 guests

  • 3 bedrooms

Woodstock, Ulster County

This Woodstock residence is one for the design-savvy folk. Once a studio belonging to acclaimed realist painter Reginald Marsh, the space has been transformed into a stunning family home.


We selected the top 3% holiday homes in Shelter Island Homes for Five People

Explore the 376 most perfect homes in our collection

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Most popular homes in Shelter Island

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Sea Urchin Escape

Sea Urchin Escape

  • 6 guests

  • 3 bedrooms

Provincetown, Barnstable County

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Autumnal Colours

Autumnal Colours

  • 6 guests

  • 3 bedrooms

Greene County, Durham

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, New York

Tucked In The Trees

Tucked In The Trees

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

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Frequently asked questions

Explore our collection of homes for 5 people in Shelter Island. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book today and enjoy a short or extended stay in the best 5 person homes that Shelter Island has to offer. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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