Urban Vistas
4 guests
2 bedrooms
Rush & Division, Chicago
This Illinois apartment won us over the moment we clapped eyes on the sweeping views of Chicago’s skyline and that private balcony. But the perks don’t end there.
Rent Cook County Homes with Swimming Pools
We selected the 18 homes worth renting in this location
Home spotlights in Cook County
The High Way
4 guests
2 bedrooms
Rush & Division, Chicago
This smart city sanctuary boasts incredible views across the Chicago skyline. The rooms have been thoughtfully designed to inspire ease and relaxation.
Chicago Charisma
5 guests
2 bedrooms
Chicago Loop, Chicago
Immerse yourself in the heart of downtown at this retreat tucked away in Chicago's vibrant Financial District. Each experience here invites a journey into iconic city attractions, folds back layers of historic architectural treasures, and strolls along river cruises or the fabled Riverwalk.
We selected the top 3% holiday homes in Cook County Homes with Swimming Pools
Explore the 18 most perfect homes in our collection
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Frequently asked questions
You've certainly come to the right place if you are hoping to find one of the finest Holiday Homes with Swimming Pools in Cook County, Illinois, United States. 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 Cook County Home to Rent with a Swimming Pool today, and set up a holiday to remember.
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