Book Family Friendly Rentals in Orange County

We selected the 812 homes worth renting in this location

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Home spotlights in Orange County

Salty Kiss

Salty Kiss

  • 5 guests

  • 2 bedrooms

Riverhead, The Hamptons

The summer retreat for Manhattan’s wealthy elite, the vibe of the Hamptons couldn’t be further from New York’s chaotic urban sprawl. And if you’re looking for the ultimate in serenity and tranquility, this idyllic beach house is for you.

The Masterplan

The Masterplan

  • 10 guests

  • 4 bedrooms

Tunkhannock Township, Monroe County

Just a two-hour drive from New York City, this home in the Poconos is more like a private resort, with an impressive list of amenities and all kinds of entertainment options for a large group. Set less than ten minutes away from scenic Lake Harmony by car, and close to various ski resorts like Jack Frost and Big Boulder Mountain, there are shops and restaurants within a few minutes drive, along with nearby golf courses and a water park.

Burnt Sienna

Burnt Sienna

  • 4 guests

  • 2 bedrooms

Marbletown, New York

Nestled in the woodlands, this cabin provides cosy comfort and stylish charm. The outdoor area is the perfect place to keep toasty by the fire and eat delicious meals.

A Timeless Tale

A Timeless Tale

  • 6 guests

  • 3 bedrooms

Greenwood Lake, Warwick

Although a modern build, this home was designed with the craftsman style in mind. It has a twenty-first century edge that gives it just enough luxury to make it both homely and wonderfully opulent for that perfect vacation.


We selected the top 3% holiday homes in Orange County Family Friendly Rentals

Explore the 812 most perfect homes in our collection

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Most popular homes in Orange County

The Great Frontier

The Great Frontier

  • 4 guests

  • 1 bedrooms

Chatham, New York

Long Story Short

Long Story Short

  • 4 guests

  • 2 bedrooms

Montauk, East Hampton

Building Bridges

Building Bridges

  • 4 guests

  • 2 bedrooms

Astoria, Queens

The Mountain Glow

The Mountain Glow

  • 6 guests

  • 3 bedrooms

Callicoon, New York

The Creekside Cabin

The Creekside Cabin

  • 2 guests

  • 1 bedrooms

Jewett, New York

The Edge

The Edge

  • 6 guests

  • 3 bedrooms

Ulster County, Rochester

Long Point

Long Point

  • 8 guests

  • 4 bedrooms

Noyack, Southampton

Summer Fridays

Summer Fridays

  • 10 guests

  • 5 bedrooms

Northwest Harbor, East Hampton

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Frequently asked questions

Discover the ultimate collection of luxury Family Friendly Rentals in Orange County. Here at Plum Guide, we prioritise customer satisfaction over everything, which is why we are so meticulous in what we do. Every home in our collection has been put through a vigorous 150-step vetting process, so we promise consistent quality you can count on. Each rental also comes fully furnished will essential bathroom toiletries, an excellently-equipped kitchen, and all linen included. Rent Orange County Family Friendly Homes now and secure yourself a trip to remember for all the right reasons. And call on the help of our friendly team, on standby night and day to ensure that your decision process is made as straightforward as possible.

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