Rent Orange County Homes with Swimming Pools

We selected the 6 homes worth renting in this location

Home spotlights in Orange County

Hudson Grandeur

Hudson Grandeur

  • 16 guests

  • 8 bedrooms

Cornwall, Orange County

This grand, old home in the Hudson Valley feels like a mix between a beautiful Midwest farmhouse and an English manor. A blue clapboard facade and white bannisters suggest country-chic while the pristine white columns at the entrance add the grandeur.

Monroe Mountain Retreat

Monroe Mountain Retreat

  • 16 guests

  • 5 bedrooms

Blooming Grove, New York

Nestled amongst Balsam Firs and Black Spruce trees is a home that invites you to indulge in rest and creativity. This impressive, upstate escape combines the charm of New York State architecture with a sumptuously modern interior that has been designed to exceed expectations.

The Autumn

The Autumn

  • 10 guests

  • 5 bedrooms

Chester, New York

Sitting peacefully at the end of a quiet road, this home makes for the perfect setting for friends and family to gather and celebrate life’s special moments. From fun-filled games of pool and ping pong to heart-warming gatherings around the table and cosy movie nights by the fire, this is the kind of setting that brings warmth and comfort to daily living.

Willow Tree View

Willow Tree View

  • 8 guests

  • 4 bedrooms

Blooming Grove, New York

Secluded away behind nearly 7 acres of shady willow trees and verdant stunning forest, this spacious compound makes for one scenic woodland retreat. With two kitchens, two reception areas, plus a multitude of dining tables split across two buildings, there’s plenty of space for everyone to roam.


We selected the top 3% holiday homes in Orange County Homes with Swimming Pools

Explore the 6 most perfect homes in our collection

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Most popular homes in Orange County

The Picket Fence

The Picket Fence

  • 16 guests

  • 8 bedrooms

Blooming Grove, New York

The Old and the Light

The Old and the Light

  • 22 guests

  • 8 bedrooms

Stony Point, Rockland County

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Frequently asked questions

You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Orange County, New York, United States. Our exclusive collection consists solely of homes that have passed our thorough 150-step vetting process with flying colours, so you can book with true peace of mind, knowing that everything from decibel levels in the bedroom to a room's intangible atmosphere has been tested and approved. We don't list a huge number of homes one our site, just the right ones. Each property in our collection comes fully furnished and ready to welcome you, with a fully-equipped kitchen, essential bathroom toiletries, and all linen included. Contact our dedicated team of experts to find the perfect luxury Orange County Home to Rent with a Swimming Pool today, and set up a holiday to remember.

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