625+ Rental Villas and Private Getaways in Near South Side |
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Near South Side Villa Rentals

About Near South Side Vacation Rentals

There are more than 625 incredible getaway rentals that are available in Near 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 Near 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 Near 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 Near South Side. Places to stay near Near South Side are 989.99 ft² on average, with prices averaging $410 a night.

BedroomVillas helps you find the ideal holiday rental to create lifetime travel memories in Near 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.

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Top Private Villas, Resorts, and Rentals in Near South Side

Type Count
Holiday Apartments 553
Vacation Homes 10
B&B 1

Use these Quick Filters to Find a Vacation Rental in Near 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 Near South Side with BedroomVillas.

Weather in Near South Side, IL

View the weather forecast for Near South Side before booking your Near South Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Find Hotels, Resorts, and Rentals Nearby in these Cities & Neighborhoods


Dearborn Park 3,938 Properties
Field Museum of Natural History 3,763 Properties
John G. Shedd Aquarium 3,734 Properties
Olmec Head No 8 3,727 Properties
National Vietnam Veterans Art Museum 3,553 Properties
Soldier Field 3,548 Properties
Glessner House Museum 3,533 Properties
Copernicus Statue 3,532 Properties
William K Kimball House 3,490 Properties
South Side 544 Properties
South Loop 533 Properties
Prairie District 404 Properties

Complexes around Near South Side, IL


Wells Apartments St Chicago 31 Properties
South Loop Grant Park 29 Properties
Sonder South Wabash 11 Properties
Mccormick Place 5 Properties
Grant Park Hotel 3 Properties
Michigan Avenue 3 Properties

Frequently Asked Questions About Near South Side?

What are the top hotels or resorts in Near South Side?

We provide an array of great vacation destinations in Near South Side. If you are looking to stay in or around the Near 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 Near South Side:

How many vacation rentals have private pools in Near South Side?

We have 6 luxury villas and vacation rentals featuriung a private pool in and near Near South Side. Some of the best destinations to stay that feature or have access to a swimming pool are:

Which hotel or resort in Near South Side is best for families?

Searching for a family-friendly getaway in Near 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.

How many hotels, resorts, or rentals are available in Near 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 2025 is over 625 in the Near 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 Near South Side. 

Nearby Neighborhood (7) 
Neighborhood Property Count
Downtown Chicago Rental Villas and Private Getaways in Chicago, Illinois 2238
South Loop Rental Villas and Private Getaways in Chicago, Illinois 533
Prairie District Rental Villas and Private Getaways in Chicago, Illinois 404
Bronzeville Rental Villas and Private Getaways in Chicago, Illinois 124
Printers Row Rental Villas and Private Getaways in Chicago, Illinois 4021
Ickes Praire Homes Rental Villas and Private Getaways in Chicago, Illinois 2027
Chicago Museum Campus Rental Villas and Private Getaways in Chicago, Illinois 3407

People Also Ask

There are 21 hotels in Near South Side 23 resorts, and 563 rentals

Recently Booked Hotels, Resorts, or Rentals in Near South Side