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.
Long Island Haven
12 guests
5 bedrooms
Brookhaven, The Hamptons
This home once served as a farmhouse in the Long Island countryside, but today it provides a rustic escape just an hour away from the city. Originally built in 1815, you’ll see vestiges of its original features – multiple wood-burning fireplaces, grand staircases and herringbone brick floors give the home its traditional charm.
Hawk & Falcon
10 guests
4 bedrooms
Ulster County, Rochester
Unplug, tune out and drop off the grid for a while. Nestled out of the way in the Rondout Valley in Upstate New York, this secluded barn house and cottage combo is perfect for anyone looking to get away from it all.
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.
Explore the 110 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 Montauk. 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 Montauk Home to Rent with a Swimming Pool today, and set up a holiday to remember.
