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.
Hampton Set
6 guests
4 bedrooms
Northwest Harbor, East Hampton
Live your best East Hampton life at this light-filled, mid-century architectural gem, just a seven-minute drive from the beach. With its private pool and hot tub, grassy lawns backed by juniper trees for post-pool games (table tennis, anyone?
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.
Summer Fridays
10 guests
5 bedrooms
Northwest Harbor, East Hampton
A haven of tranquillity, this serene home is perfect for recharging your batteries. Step inside and be soothed by the classic Hamptons style – think ample-sized living spaces designed for entertaining, calm colours inspired by the coast and oodles of windows flooding each room with natural light.
Explore the 102 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 Brookhaven. 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 Brookhaven Home to Rent with a Swimming Pool today, and set up a holiday to remember.
