Compare Vacation Rentals & Rent By Owner Homes in Near South Side, Chicago, Illinois, USA
About Near South Side Vacation Rentals
With more than 489 Near South Side vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Near South Side.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Near South Side, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Near South Side. Places to stay near Near South Side are 947.09 ft² on average, with prices averaging US $415 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Near South Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Near South Side, IL
Near South Side Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Near South Side?
- MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba
- Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area
- Luxéry Stay South Loop - McCormick/Wintrust Area
- Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
- 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
- 420 friendly 3BR/2BA heaven with optional parking
- McCormick Place 2b/2b family unit with optional parking for up to 8 guests
- Family and Group Friendly 5BR Spacious Unit with Pool Table and Optional Parking Near McCormick Place and Soldier Field
How many Rentbyowner vacation rentals are available in Near South Side?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 489 in the Near South Side area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Near South Side.
Nearby Neighborhood (7)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Vacation Rentals in Chicago, Illinois | 2261 |
| South Loop Vacation Rentals in Chicago, Illinois | 390 |
| Prairie District Vacation Rentals in Chicago, Illinois | 278 |
| Bronzeville Vacation Rentals in Chicago, Illinois | 112 |
| Printers Row Vacation Rentals in Chicago, Illinois | 4021 |
| Ickes Praire Homes Vacation Rentals in Chicago, Illinois | 2027 |
| Chicago Museum Campus Vacation Rentals in Chicago, Illinois | 3407 |
