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Southold Luxury Rentals

We selected the best homes worth renting in this location

Home spotlights in Southold

Well & Happy

Well & Happy

  • 10 guests

  • 5 bedrooms

Southold, The Hamptons

Just steps from the beach with views across Peconic Bay, this home brings ease and comfort to coastal living. Bikes are provided for exploring and it’s just a short drive to the restaurants and shops of Southold.

Like a Whisper

Like a Whisper

  • 11 guests

  • 7 bedrooms

Peconic, North Fork

This home has everything a group of friends or family need for a comfortable stay in Long Island's North Fork. The space is spread across three floors and although the decor is a little dated, there's lots to like.

We selected the top 3% holiday homes in Southold Luxury Rentals

Explore the 2 most perfect homes in our collection

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Check upcoming rates & availability for Southold Luxury Rentals

This weekend

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03 May - 05 May

Next weekend

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10 May - 12 May

One week next month

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12 May - 19 May

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A handpicked selection of the best luxury homes in Southold, The Hamptons, Suffolk County, New York, United States, as chosen by the experts who've visited and vetted thousands of the city's homes. Luxurious interiors, sumptuous bedrooms and prime city centre locations. Available for short and extended stays.

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