Walcott
8 guests
3 bedrooms
Bridgehampton, Southampton
With a swimming pool outside and a huge playroom inside, there's no chance of boredom at this Hamptons retreat. Set in luscious forest near Bridgehampton and Sag Harbor, you're a short drive from shops, restaurants, and activities, while being secluded in your own peaceful bubble.
Sweet Cicely
6 guests
3 bedrooms
Ulster County, Woodstock
Set in 15 acres of private grounds, this modern mountain chalet in New York’s Catskills is the ultimate Upstate getaway. Inside, the place is rustic yet refined with timber vaulted ceilings, mid-century modern furnishings and a creamy colour palette.
Coastal Rhapsody
12 guests
7 bedrooms
Stonington, New London County
If you’re in search of a coastal adventure or a relaxing beachfront escape, this home delivers the perfect solution. Nestled in Stonington village, you’ll be spoiled by beautiful views, an expansive two acres of lush grounds, a private pool and a tennis court.
Life As A Dream
8 guests
4 bedrooms
Montauk, East Hampton
Whether it's alfresco dining, sun lounging or sitting around the fire pit at sunset, this beautiful house has seating for almost every occasion. And found only five minutes from the beach, it's calling on sun worshippers everywhere to come and enjoy the drop-your-bags-and-go proximity.
Explore the 68 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 The Hamptons, Suffolk 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 The Hamptons Home to Rent with a Swimming Pool today, and set up a holiday to remember.
