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We selected the 912 luxury monthly villas and homes worth renting in this location

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Home spotlights in Shelter Island

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Set within an acre of lush green grounds, this seriously charming home is just a twenty-minute drive from the centre of Sag Harbour - undoubtedly one of New York State's best-kept secrets. This centuries-old seaside village may be known as one of the most family-friendly places in the Hamptons, but its strictly adults-only activities include a visit to the nearby Wölffer Estate vineyards to sample their famed rosé cider.

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.

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.

Sunflowers & Wisteria

Sunflowers & Wisteria

  • 11 guests

  • 5 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, Nora Ephron and John Steinbeck.


We selected the top 3% holiday homes in Shelter Island Long Stay Rentals

Explore the 912 most perfect homes in our collection

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Most popular homes in Shelter Island

Mystic Countryside Farm

Mystic Countryside Farm

  • 4 guests

  • 2 bedrooms

North Stonington, New London County

Hampton Set

Hampton Set

  • 6 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Wander Inn

Wander Inn

  • 6 guests

  • 2 bedrooms

Southold, The Hamptons

Villa Menantic

Villa Menantic

  • 8 guests

  • 4 bedrooms

Shelter Island Heights, Shelter Island

Dappled Sunlight

Dappled Sunlight

  • 8 guests

  • 4 bedrooms

Northwest Harbor, East Hampton

Seascape

Seascape

  • 8 guests

  • 5 bedrooms

Noyack, 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

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Check upcoming rates & availability for Shelter Island Long Stay Rentals


Frequently asked questions

Explore our collection of luxury Extended Stay Rentals available for you to rent in Shelter Island. Each and every home you'll find has been through a meticulous, multi-stage vetting process to ensure quality our guests can always count on. The Long Stay Rentals in our Shelter Island collection come fully furnished with well-equipped kitchens, all linens, and essential bathroom toiletries included. And if you need any assistance, our friendly team of experts is always on hand to help plan your perfect stay.

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