The Little Sparrow
6 guests
3 bedrooms
Shinnecock Hills, Southampton
Radiating coastal luxury, this towering home with its streamlined kitchen, natural lighting and picture-perfect minimalist rooms stands on an acre of land in the affluent Hamptons. Location-wise, you're surrounded by art museums and trendy mom-and-pop shops, with the historic Shinnecock Hills Golf Club under five minutes away by car and Meschutt Beach not much further.
Lost In The Mountains
10 guests
3 bedrooms
Pocono Pines, Tobyhanna Township
A waterfront home in the Pocono Pines – yes please. Huge windows make it feel like you’re in the middle of the forest, though you’ll be able to pay for access to a premium club nearby, where you can golf, swim and play tennis – you get the peace of the wilderness with the amenities of a resort.
Whale Watching
8 guests
4 bedrooms
Sag Harbor, Southampton
Arriving at this effortlessly chic seaside home from the city is a shockingly swift affair – you can be in Manhattan for breakfast and Sag Harbour for lunch. With its white-washed interiors and beachy accents, the home is ideal for a family of weekenders or those looking for a long-term change of scenery.
Tudoresque
10 guests
5 bedrooms
Ossining, Westchester County
In the town of Ossining on the banks of the Hudson River, this home is reminiscent of an English Tudor mansion on the outside. Inside, there’s plenty of social space for the group to spread out – playing a game of pool in the main living room, settling in to watch Netflix by the fire, in the dedicated media room upstairs or perhaps sipping an old fashioned at the wet bar in the “sky lounge” at the top of the house.
Explore the 112 most perfect homes in our collection
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. 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.
