Book Luxury Summer Rentals in Shelter Island

We selected the 902 homes worth renting in this location

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Age 13+

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Age 1 to 12

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Home spotlights in Shelter Island

Hamptons Dreams

Hamptons Dreams

  • 9 guests

  • 3 bedrooms

East Hampton North, East Hampton

Exploring East Hampton is a breeze at this coastal cottage. Both downtown and the beach are easily accessible by bike, and a coffee shop and seafood restaurant are just down the street.

Coastal Rhapsody

Coastal Rhapsody

  • 12 guests

  • 7 bedrooms

Stonington, New London County

If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.

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?

Cruising The Coast

Cruising The Coast

  • 6 guests

  • 3 bedrooms

Sag Harbor, Southampton

This quintessential clapboard home in Sag Harbor is sure to pique the interest of travellers looking for a relaxing stay in the Hamptons. With its close proximity to the coast, including Haven's beach, the home is conveniently located for exploring the area.


We selected the top 3% holiday homes in Shelter Island Vacation Rentals for Summer

Explore the 902 most perfect homes in our collection

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Most popular homes in Shelter Island

The Whaler's Cottage

The Whaler's Cottage

  • 5 guests

  • 3 bedrooms

Sag Harbor, Southampton

Old Macdonald

Old Macdonald

  • 5 guests

  • 2 bedrooms

Stamford, 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

Gift of the Sea

Gift of the Sea

  • 6 guests

  • 2 bedrooms

Nantucket County, Massachusetts

Sunflower Summer

Sunflower Summer

  • 7 guests

  • 3 bedrooms

Springs, East Hampton

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

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Check upcoming rates & availability for Shelter Island Vacation Rentals for Summer


Frequently asked questions

Explore our remarkable range of luxury Summer Rentals in Shelter Island. There's no time for average stays, so treat yourself to a stay in one of the most impressive rentals around. Each and every home in our selection is put through numerous rounds of thorough testing, with everything from shower pressure to a home's design being closely checked for quality. Only the finest 3% of homes are awarded the prestigious Plum Award, so you can book with total confidence. Rentals in our range come fully furnished, with a well-equipped kitchen, essential bathroom toiletries, and all linen included to make you feel right at home. Book a memorable trip to an unforgettable Vacation Rental for Summer in Shelter Island today, and make the most of the year's warmest season. If you require any assistance, call on the help of our experts - they're on-hand to help you discover the perfect home.

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