The Urban Villa
6 guests
2 bedrooms
Rush & Division, Chicago
A striking interplay between tradition and trend elevates this property nestled within the vibrant Streeterville neighbourhood. Combining nostalgic tales of Chicago's history with an undercurrent of worldwide allure, it resonates an Italian villa's flair and far-reaching design sensibilities.
The Heart of the Loop
16 guests
8 bedrooms
Chicago Loop, Chicago
Welcome to a holiday getaway nestled right in the heart of Chicago’s vibrant Financial District. Just steps from iconic attractions, revel in the rich history of the city through its grand architecture and marvel at the stunning skyline from this retreat.
Chicago Chill Pad
5 guests
2 bedrooms
Chicago Loop, Chicago
Here awaits The Cooke, where guest security and solace are paramount. Ensconced in the heart of Chicago's distinguished Financial District, this property is a gateway to an array of unforgettable Windy City attractions.
Charming Chicago Charm
5 guests
2 bedrooms
Chicago Loop, Chicago
Welcome to a gem nestled in the heart of Chicago's Financial District, offering guests a unique blend of historical architecture, city excitement and stunning views over the Chicago Riverwalk. The location is unmatched, mere steps away from Millennium Park and State Street, both alive with incredible cuisine and eclectic shopping experiences.
Explore the 18 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 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.
