South Side Villa Rentals
About South Side Vacation Rentals
There are more than 556 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 796.09 ft² on average, with prices averaging US $457 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.
Top Private Villas, Resorts, and Rentals in South Side
| Type | Count |
|---|---|
| Holiday Apartments | 441 |
| Vacation Homes | 22 |
Use these Quick Filters to Find a Vacation Rental in South Side
★ Pro Tip: BedroomVillas is a luxury vacation rental website, pulling some of the top private villas and exclusive holiday stays from sources across the web. We supply you with a huge list of incredible beach houses and holiday rentals from trusted, reliable suppliers, helping you to compare prices and locations to find the best fit for your getaway. Create lifelong memories in South Side with BedroomVillas.
Weather in South Side, IL
View the weather forecast for South Side before booking your South Side Vacation Rentals to confirm your best time to go.
Stay Near South Side's Top Attractions
A Large Selection of Villas and Vacation Rentals from Around the World South Side's Research Top Attractions For Your Vacation
Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods
Complexes around South Side, IL
Frequently Asked Questions About South Side?
What are the top hotels or resorts in South Side?
We provide an array of great vacation destinations in South Side. If you are looking to stay in or around the South Side area, make sure to browse our options to find a premium rental location in a top vacation destination. Whether it is a few nights, a week, or more, we've got the luxury stays that rank among the Top Vacation Rentals in South Side:
- Chic 2-Bedroom Townhouse with Rooftop, Free Parking, in Downtown Chicago!
- Spacious 3BR Corner Family Oasis Near McCormick Place & Soldier Field
- McCormick Apt 3BR Corner Oasis Near Soldier Field & Museum Campus
- Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront
- Spacious 3BR · Bronzeville/South Loop · Sleeps 8
- Cozy 2BR South Loop Condo with Optional Parking and Gym Near McCormick Place, Public Transit & City Hotspots
- McCormick Place Patio skyline 2b/2b with optional Parking for up to 6 people
- Spacious 2BR South Loop Suite with Skyline View, Optional Parking and Gym Access Close to McCormick Place, Grant Park, Museum Campus & CTA Lines
- South Loop · 3 Kings · Steps from McCormick Place
- South Loop Chicago 3BR Corner Suite Near Museum Campus & Millennium Park
Which hotel or resort in South Side is best for families?
Searching for a family-friendly getaway in South Side? We've got you covered. Check out one of these luxurious getaways that are highly-rated and perfect fits for families of all sizes.
- McCormick Place 2b/2b family unit with optional parking for up to 8 guests
- Cozy 3BR City Living in South Loop Near McCormick Place, Soldier Field & Lakefront
- Marriott Marquis Chicago
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 556 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 | 838 |
| The Loop Rental Villas and Private Getaways in Chicago, Illinois | 387 |
| Near West Side Rental Villas and Private Getaways in Chicago, Illinois | 185 |
| South Loop Rental Villas and Private Getaways in Chicago, Illinois | 137 |
| Near South Side Rental Villas and Private Getaways in Chicago, Illinois | 131 |
| West Loop Rental Villas and Private Getaways in Chicago, Illinois | 120 |
| Prairie District Rental Villas and Private Getaways in Chicago, Illinois | 99 |
| Lower West Side Rental Villas and Private Getaways in Chicago, Illinois | 2284 |
| Chinatown Rental Villas and Private Getaways in Chicago, Illinois | 3211 |
| Printers Row Rental Villas and Private Getaways in Chicago, Illinois | 4131 |
| Chicago Museum Campus Rental Villas and Private Getaways in Chicago, Illinois | 3309 |
