Shelter Island Coastal Homes

We selected the 116 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

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, Southampton

A luxurious harbour-front villa overlooking the serene Noyack Bay, this home's stylish interior boasts elegance and sophistication. Huge, panoramic windows display the beautiful surroundings while flooding the space with light.

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.

Technicolour Dreamland

Technicolour Dreamland

  • 6 guests

  • 3 bedrooms

Northwest Harbor, East Hampton

This colourful Hamptons home has a laid back, friendly feel that would be perfect for a group of friends or family. In a quiet part of the Northwest Woods area of East Hampton, the house is surrounded by trees which guarantees peace, quiet and privacy to enjoy your trip.

Tudoresque

Tudoresque

  • 10 guests

  • 5 bedrooms

Ossining, Westchester County

In the town of Ossining on the banks of the Hudson River, this home is reminiscent of an English Tudor mansion on the outside. Inside, there’s plenty of social space for the group to spread out – playing a game of pool in the main living room, settling in to watch Netflix by the fire, in the dedicated media room upstairs or perhaps sipping an old fashioned at the wet bar in the “sky lounge” at the top of the house.


We selected the top 3% holiday homes in Shelter Island Coastal Homes

Explore the 116 most perfect homes in our collection

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Most popular homes in Shelter Island

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Just A Minute

Just A Minute

  • 6 guests

  • 3 bedrooms

Water Mill, Southampton

The Old Life-Saving Station

The Old Life-Saving Station

  • 13 guests

  • 6 bedrooms

East Marion, Southold

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

A Country Call

A Country Call

  • 4 guests

  • 2 bedrooms

Bellport, Brookhaven

Light of Romance

Light of Romance

  • 14 guests

  • 6 bedrooms

Springs, East Hampton

Blissful Thinking

Blissful Thinking

  • 10 guests

  • 5 bedrooms

Springs, East Hampton

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Frequently asked questions

Discover a selection of the best coastal homes in Shelter Island. Plum Guide’s homes come fully furnished with the best-equipped kitchens, essential bathroom toiletries and all linen included. Book your next getaway today and enjoy a short or extended stay in the best coastal homes in Shelter Island. Our friendly team of Plum Experts are on-hand 24/7 should you need anything.

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