Beaming Smiles
6 guests
4 bedrooms
Bridgehampton, Southampton
A renovated barn complete with a heated outdoor pool, all within walking distance of Bridgehampton. This charming home ticks all the boxes, and you can even drive to the beach in a matter of minutes.
Spirited Serenity
8 guests
4 bedrooms
Water Mill, Southampton
Nestled between Southhampton and Bridgehampton, the little hamlet of Water Mill is proof that the best things do, in fact, come in small packages. Here, a thriving arts community is woven into a patchwork quilt of rolling green pastures and, along the waterfront, an elegant string of mansions owned by star-studded locals.
Elderberry Estate
8 guests
8 bedrooms
Water Mill, Southampton
Summering in the Hamptons has long been the preserve of New York's elite, and this home is heavy on nostalgia. Just the shape of it is enough to illicit a sentimental smile about years gone by.
Dragonfly Creek
6 guests
3 bedrooms
Bridgehampton, Southampton
We love the rustic farmhouse feel of this home in the Hamptons, where whitewashed beams can be found in just about every room. The open-plan living area opens out onto a large wooden deck, where you can enjoy an alfresco meal with views over the surrounding wilderness.
Explore the 18 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 Bridgehampton, Southampton, 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 Bridgehampton Home to Rent with a Swimming Pool today, and set up a holiday to remember.
