Penthouses in Shelter Island

Curated Penthouses rentals in Shelter Island

Who's coming along?

Adults

Age 13+

0

Children

Age 1 to 12

0

Infants

Under 1

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Pets

An extra fee may apply

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Home spotlights in Shelter Island

Bright City Lights

Bright City Lights

  • 8 guests

  • 4 bedrooms

Midtown South, Manhattan

Where to start with this apartment? The interiors or the location?

Manhattan Lights

Manhattan Lights

  • 10 guests

  • 5 bedrooms

Midtown South, Manhattan

When it comes to location, this apartment in Midtown Manhattan is hard to beat. It's just a short walk away from Times Square, Broadway, MoMA and Central Park.

Times Square Splendour

Times Square Splendour

  • 8 guests

  • 4 bedrooms

Midtown South, Manhattan

A Times Square location and a city skyline view is our idea of a perfect New York stay, and this penthouse apartment ticks both boxes. We love the unique two-way mirror here, and the 41-foot ceilings make the living space feel super light – perfect for breakfasts around the dining table.

Times Square Suite

Times Square Suite

  • 4 guests

  • 2 bedrooms

Theater District, Manhattan

The Times Square Suite is really something. Carefully designed by Nicholas Cardone, this apartment is adorned with premium amenities, and unique architectural features, like the exposed cast iron structures that pay homage to this historical building.


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

Explore the 30 most perfect homes in our collection

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Most popular homes in Shelter Island

Brooklyn Reign

Brooklyn Reign

  • 4 guests

  • 2 bedrooms

Greenpoint, Brooklyn

Loki's Den

Loki's Den

  • 7 guests

  • 4 bedrooms

Nolita, Manhattan

A Fairytale of New York

A Fairytale of New York

  • 4 guests

  • 2 bedrooms

Rose Hill, Manhattan

Skyline Fairytale

Skyline Fairytale

  • 3 guests

  • 2 bedrooms

Williamsburg, Brooklyn

The Thomas Edison

The Thomas Edison

  • 2 guests

  • 1 bedrooms

Williamsburg, Brooklyn

Tinted Whispers

Tinted Whispers

  • 4 guests

  • 2 bedrooms

Chelsea, Manhattan

Soho Playground

Soho Playground

  • 4 guests

  • 2 bedrooms

SoHo, Manhattan

The Secret of Manhattan

The Secret of Manhattan

  • 4 guests

  • 2 bedrooms

SoHo, Manhattan

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Check upcoming rates & availability for Shelter Island Penthouses


Frequently asked questions

Look forward to a memorable stay in one of the finest Penthouse Rentals that Shelter Island has to offer. Our exclusive collection contains only the very best homes, with just the top 3% earning the prestigious Plum Award. Our meticulous Home Critics test everything from shower pressure to a home's design, so you can book your holiday with complete confidence. Each home in our range comes fully furnished too, with the best-equipped kitchens, essential bathroom toiletries, and all linen included. Rent one of Plum Guide's luxury Shelter Island Penthouses today, with the help of our friendly team of experts, and see what all the fuss is about.

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