Near South Side vacation rentals
We found 1,331 vacation rentals — enter your dates for availability
Discover a selection of 7 homes and other vacation rentals in Near South Side that are perfect for your trip. Vacation rentals offer the amenities you expect for your family, friends, or furry companion, such as a hot tub and a washer and dryer. You'll be sure to find a rental that has what everyone needs, including places that are non-smoking or accessible.
Find spaces that suit your style
Cabin
Cottage
Find properties near top attractions in Near South Side
Map Attractions
Find the best place to stay - Near South Side
Luxéry Stay South Loop - McCormick/WinTrust Area
Sleeps 8 · 3 bedrooms · 2 bathrooms
10 out of 10
exceptional
(5 reviews)
Top rated rentals - Near South Side
Fabulous, fantastic, and fab!!
10 out of 10
exceptional
(17 reviews)
- Peace of mindOur Book with Confidence guarantee gives you 24/7 support
- More quality timeFrom booking to staying, the whole process is simple and enjoyable
- All the privacy of homeEnjoy full kitchens, laundry, pools, yards and more
- More for lessMore space, more privacy, more amenities — more value