Downtown Chicago rentals with pool

We found 555 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • 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

How much does it cost to stay in a holiday rental with a pool in Downtown Chicago?
Plunge pool or rooftop pool, compact or sprawling, peak season or low season — how much you'll pay for your stay in Downtown Chicago is influenced by all sorts of factors. But the one consistent element? Our holiday rentals with a pool are where awesome family memories are made. To find a place that fits your budget, narrow your search results by price. You can also use our "Discounts" filter to find holiday rentals that offer weekly or monthly discounts.
When is the best time to book a holiday rental with a pool in Downtown Chicago?
The most popular month to book a holiday rental with a pool in Downtown Chicago is March. Do a little research to find the best time to kick back poolside in between adventures. Aside from the weather, consider the high, shoulder and low seasons of your destination, as this can impact prices, crowds and availability.
What holiday rentals with a pool in Downtown Chicago have nice views?
Relaxing comes easy at Stayz's holiday rentals with a pool in Downtown Chicago. Take a dip in the water or simply gaze at the outlooks. Tailor your search by "Recommended" or "Guest rating" to see exceptional stays where you can lose yourself in the stunning scenery as your cares drift away.
Are there holiday rentals with a private pool in Downtown Chicago?
From splashing around with the kids to midnight swims under the stars, a holiday rental with a private pool gives you plenty of possibilities for relaxation and fun. If you're on your way to Downtown Chicago, use our "Private pool" filter to search for accommodation that come with this exclusive amenity.
What are the top things to do in Downtown Chicago?
Venture out and immerse yourself in everything Downtown Chicago has to offer from the comfort of your holiday home rental. We recommend doing some research on what you'd like to see and do, so you can plan the perfect getaway.
Why should I book my holiday rental with a pool with Stayz?
When you stay in a Stayz holiday rental with a pool, the only people you have to share your space with are those you take with you. It'll just be you and your nearest and dearest with the entire place to yourselves enjoying a splashing good time. Our flexible cancellation policies also mean you can book your rental house with confidence if you have to change your plans.
Rentals with Pool in Downtown Chicago
Rentals with Pool near LINEA