Compare Villas, Resorts, & Rentals in South Side, Illinois, USA
About South Side Vacation Rentals
There are more than 525 incredible getaway rentals that are available in South Side. These choices include villas, hotels, and other rental options. Browse from a massive selection of luxury amenities at great prices, providing you with the dream spot to base your next vacation. Relax with BedroomVillas and uncover great stays in South Side.
BedroomVillas features numerous last-minute deals on villas, hotels, and rentals, in locations near you or across the globe. If you need a place for a group or event, be it a hotel or vacation rental (as well as cabins and private luxury villas), let us help. With BedroomVillas in South Side, you can compare options from multiple suppliers with a single click to find the price point, amenities, and style of stay that works for you. Group deals, private pools, hot tubs, allows pets, or even huge master suite bedrooms with open-air showers? You can find it all with the BedroomVillas vacation rentals, resorts, and Airbnb-style properties in South Side. Places to stay near South Side are 891.91 ft² on average, with prices averaging AU $545 a night.
BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in South Side. Prices listed are often found to be discounted versus the rack rates. Just search for your destination and secure your perfect place to stay today.
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods South Side, IL
Frequently Asked Questions About South Side?
What are the top hotels or resorts in South Side?
- MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
- 1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown
- 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
- Stylish 2BR South Loop Family Unit Near McCormick Place & Soldier Field
- Luxéry Stay "Chicago" Downtown/McCormick/Wintrust Area
- 2BR South Loop Apt—Walk to Lake, Museums, Aquarium + Pool, Gym, WiFi, & Conv Ct
- Comfy 3BR Chicago Retreat 420 Friendly Unit Near McCormick Place & Soldier Field
- Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field
How many hotels, resorts, or rentals are available in South Side?
BedroomVillas offers a consistent supply of new options, combined with established great stays in top areas. Currently, the number of properties listed by BedroomVillas in 2026 is over 525 in the South Side area, and that number rises every day. By combining listings from multiple websites and travel providers, BedroomVillas can provide you with a diverse amount of choices of the best luxury stays in South Side.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Downtown Chicago Rental Villas and Private Getaways in Chicago, Illinois | 1541 |
| The Loop Rental Villas and Private Getaways in Chicago, Illinois | 711 |
| Near West Side Rental Villas and Private Getaways in Chicago, Illinois | 375 |
| South Loop Rental Villas and Private Getaways in Chicago, Illinois | 367 |
| Near South Side Rental Villas and Private Getaways in Chicago, Illinois | 352 |
| Prairie District Rental Villas and Private Getaways in Chicago, Illinois | 251 |
| West Loop Rental Villas and Private Getaways in Chicago, Illinois | 217 |
| Lower West Side Rental Villas and Private Getaways in Chicago, Illinois | 55 |
| Printers Row Rental Villas and Private Getaways in Chicago, Illinois | 3802 |
| Chinatown Rental Villas and Private Getaways in Chicago, Illinois | 2948 |
| Chicago Museum Campus Rental Villas and Private Getaways in Chicago, Illinois | 3119 |
