Book Luxury Rental Apartments in Shelter Island

We selected the 608 homes worth renting in this location

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Home spotlights in Shelter Island

Antique Pine

Antique Pine

  • 6 guests

  • 2 bedrooms

Pine Bush, Crawford

In the quiet hamlet of Pine Bush on the outskirts of the Hudson Valley, this charming 1920s apartment is the perfect space to get away from it all. The interior is an eclectic blend of styles, expertly mixing antique furniture and period features with modern finishes.

The Art Enthusiast

The Art Enthusiast

  • 4 guests

  • 2 bedrooms

SoHo, Manhattan

This chic, light-filled loft boasts an envy-inducing location in the heart of Soho. Huge windows and 14-foot ceilings mean that it’s a bright and welcoming home, with an open-plan living and dining space that’s sure to impress even the most discerning travellers.

Chic Loft Retreat

Chic Loft Retreat

  • 6 guests

  • 3 bedrooms

NoHo, Manhattan

This striking loft sits in the heart of Noho, an in-demand neighbourhood. Just a five-minute walk from Soho and Greenwich Village, this loft is in a convenient location, whether you’re in town for business or leisure.

The Stuntman

The Stuntman

  • 6 guests

  • 4 bedrooms

Civic Center, Manhattan

Experience high-end Manhattan living at this spectacular apartment, boasting a rare 1500 sqft private deck complete with seating and lights. Indoors you'll find a dedicated study with a Steinway piano and guitar, a library of books and a desk for remote working.


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

Explore the 608 most perfect homes in our collection

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Most popular homes in Shelter Island

Hell's Kitchen Chic

Hell's Kitchen Chic

  • 2 guests

  • 1 bedrooms

Hell's Kitchen, Manhattan

New York Moment

New York Moment

  • 6 guests

  • 4 bedrooms

Financial District, Manhattan

Hawk & Falcon

Hawk & Falcon

  • 10 guests

  • 4 bedrooms

Ulster County, Rochester

Broadway and Beyond

Broadway and Beyond

  • 4 guests

  • 2 bedrooms

Hell's Kitchen, Manhattan

Greenwich Oasis

Greenwich Oasis

  • 4 guests

  • 2 bedrooms

South Village, Manhattan

East Side Chic

East Side Chic

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

Urban Sophistication

Urban Sophistication

  • 2 guests

  • 1 bedrooms

Lenox Hill, Manhattan

With a View

With a View

  • 4 guests

  • 2 bedrooms

Lenox Hill, Manhattan

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Frequently asked questions

There's no better place to book luxury Holiday Apartments in Shelter Island than our exclusive Plum Guide collection, which includes only the top 3% of homes. Every one of the homes on our site has been put through a painstaking vetting process with 150 checkpoints, culminating in a visit from a professional Home Critic. Every one of the remarkable homes on our books come fully furnished, with all linen and essential bathroom toiletries included, as well as a perfectly-equipped kitchen. Choose from one of the 608 Apartments for Rent in our Shelter Island range, and discover the true meaning of luxury. Call on the help of our dedicated team too, to help make your choice as straightforward as possible.

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