Jewel on the Hudson
12 guests
5 bedrooms
Coxsackie, New York
This riverfront home is the kind of getaway we dream of every day. The infinity pool and views of the Hudson River are magnificent – just imagine how calming it is to wake up to views of this calibre every day.
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.
A Faithful Friend
10 guests
6 bedrooms
Water Mill, Southampton
This home is nearly a hundred years old, but in terms of its luxury and comfort, it might as well be brand new. Once you’ve had a flick through the photos, you won’t be surprised to find out that it’s been featured in many design magazines.
The Striped Sea Bass
6 guests
3 bedrooms
Bay Point, Noyack
If you’re looking for all the charm of a country cottage with the space and grandeur of a manor house, this is the spot for you. It’s a four-minute stroll to the vast stretch of sand at Long Beach and a six-minute drive sees you in the heart of the pretty village of Sag Harbor.
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 Shelter Island. 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 Shelter Island Home to Rent with a Swimming Pool today, and set up a holiday to remember.
