Rent Luxury Accommodation in Shelter Island

We selected the 920 homes worth renting in this location

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Age 1 to 12

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Home spotlights in Shelter Island

Long Island Iced Tea

Long Island Iced Tea

  • 8 guests

  • 3 bedrooms

Remsenburg, Remsenburg-Speonk

Not too far from the bright lights of New York City, this striking and stylish home sits near the beaches of Westhampton and among the protected marshlands of Long Island. The house itself is a modern twist on the traditional clapboard homes the area is famous for, with wraparound decks looking into the treetops to the rear and plenty of sliding doors allowing the indoors to seamlessly slip into the outdoor space.

Where the Wind Blows

Where the Wind Blows

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

At the bottom of the garden, you’ve got direct access to the serene waters of Noyack Bay, with kayaks, paddleboards and bicycles provided by your host. It’s a fifteen to twenty-minute walk (or five-minute cycle) to the restaurants and grocery store of Noyack, just along the coast from Sag Harbour.

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 Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

This NYT-featured Catskills home is not quite the cabin it seems to be. What looks like a single storey home from one angle is actually built over a creekside slope, and we think it's one of the most interesting places we've seen for a peaceful stay in the woods.


We selected the top 3% holiday homes in Shelter Island Accommodation

Explore the 920 most perfect homes in our collection

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Most popular homes in Shelter Island

Magic in The Hamptons

Magic in The Hamptons

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

A Summer's Eve

A Summer's Eve

  • 15 guests

  • 7 bedrooms

Greenburgh, Westchester County

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Art & Nature

Art & Nature

  • 6 guests

  • 4 bedrooms

Cragsmoor, Wawarsing

When In Bloom

When In Bloom

  • 6 guests

  • 3 bedrooms

Southampton, The Hamptons

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 bedrooms

Springs, East Hampton

Straight Down the Middle

Straight Down the Middle

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

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Frequently asked questions

Take a look at our exclusive collection of luxury Accommodation in Shelter Island, and find your dream home. Each and every listing on our site has passed a vigorous testing process with flying colours, which is why we can be so certain that our collection is the best of the best. Only 3% of homes will ever make it onto Plum Guide, emphasising our incredibly high standards and making your job as easy as possible. Every home comes fully furnished with a perfectly-equipped kitchen, essential bathroom toiletries, and all linen included, so you will find everything you need. Get in contact with our friendly team of experts, whose sole purpose is to find you your ideal home, and book your stay in the finest Shelter Island Accommodation for Rent.

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