Hudson Grandeur
16 guests
8 bedrooms
Cornwall, Orange County
This grand, old home in the Hudson Valley feels like a mix between a beautiful Midwest farmhouse and an English manor. A blue clapboard facade and white bannisters suggest country-chic while the pristine white columns at the entrance add the grandeur.
Racquet & Relax
12 guests
5 bedrooms
Remsenburg, Remsenburg-Speonk
If you’re in search of the ultimate Hamptons escape, this home delivers a refreshing solution. From the saltwater heated pool and hot tub to the private tennis court, every detail has been considered to bring you a magical getaway.
Zephyr Residence
10 guests
5 bedrooms
Water Mill, Southampton
Stay in the heart of the heavenly Hamptons when you check in to this comfy home. It’s a short drive from the ocean (or ten minutes on the bikes provided by your host), and close to popular spots like Sag Harbor with its independent boutiques and quaint harbour.
Explore the 108 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.
