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Shelter Island rentals with pool

We found 1,482 rentals with pool — enter your dates for availability

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Shelter Island?
Browse our 1,482 holiday rentals with a pool and begin organising your Shelter Island trip. Whether you're going to stay in Menantic Creek, Coecles Harbour, The Heights or another well-known neighbourhood, you'll find the perfect poolside retreat on Stayz.
How much does it cost to stay in a holiday rental with a pool in Shelter Island?
If you're hoping to save on your holiday rental with a pool, Stayz's filters can help. Once you've done your initial search, tailor your results according to your preferences, including price, location and features and amenities. We've got holiday homes in Shelter Island for all types of budgets, so make the most of our filters to find your dream stay.
When is the best time to book a holiday rental with a pool in Shelter Island?
Look up the temperatures during different seasons, especially if you want a property with an outside pool. Also be mindful of any periods that have higher demand, as this will impact availability and prices. If you need help working out the right time to book your holiday rental with a pool in Shelter Island, join online travel communities to gain insights from fellow adventurers.
What holiday rentals with a pool in Shelter Island have nice views?
When searching for your holiday rental with a pool in Shelter Island, take advantage of our "Location" filter. This lets you choose the sorts of areas you'd like to stay in, whether that's around nature or somewhere central. Pick your favourite and be sure to bring your swimsuit.
Are there holiday rentals with a private pool in Shelter Island?
Day or night, you can go swimming whenever you want when you book a holiday rental with a private pool in Shelter Island. To look for Stayz properties that'll add an extra layer of fun to your escape, use our "Private pool" filter.
What are the top things to do in Shelter Island?
Fun times in Shelter Island are on the agenda for the fam when you book a holiday home rental with a pool. As well as visiting top attractions like East Hampton Main Beach, Orient Point County Park and 67 Steps Beach, you'll be able to spend your downtime poolside.
Why should I book my holiday rental with a pool with Stayz?
Whether you're travelling as a couple or with the family, staying at a holiday rental with a pool promises a new level of relaxation and fun to your break. And finding the right pad is a breeze with our handy filters. Simply narrow your search by amenities, location, budget and more, then lock in your favourite. Another great reason to book with us is our flexible cancellation policies. If you have to change plans, you'll get a 100% refund as long as you cancel within the time frame specified by the property owner.