
House holiday rentals in South Side
Find and book unique houses on Airbnb
Top-rated house rentals in South Side
Guests agree: These houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side house rentals
House rentals with a pool

Comfy 3BR 2BA, Liv+Fam Rm, Prime, 3-Car Parking

2BR w/ Stunning Views and Resort-Style Amenities

Munster hide away

Spacious 3 Floor Townhome

Now Open: Heated Pool with Entire House

Unique 3BR Escape/ Pool, Vintage Decor & Big Yard

Luxury Loft with Private Pool and Movie Theater

Little Pink House Downtown
Weekly house rentals

Chicago Home (1st floor) by Midway near Downtown

The Modern Muse of Chicago! Close to everything!

Amazing historic campus mansion!

CasaNova Modern City Living

Animal House near Sox stadium

Cozy Haven

Charming 3 bed home with private backyard

Spacius unit in historic gem
Private house rentals

Modern Family Townhouse

Family Friendly Duplex/9 min from MDW/Free Parking

Bronzeville 42: Art & Hospitality Mins to Downtown

Experience Chicago from Our 3-Story Retreat

Floresitas Oasis, your home in Chicago

A Comfortable Stay While You are Away in Oak Park

Villa Noir Chicago Victorian 7 min to downtown

Entire Luxury Home: Private Gym
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
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- Rentals with a hot tub South Side
- Rentals with a patio South Side
- Townhouse rentals South Side
- Rentals with a washing machine and dryer South Side
- Rentals with breakfast South Side
- Waterfront rentals South Side
- Bed and breakfasts South Side
- Smoking-friendly rentals South Side
- Rentals with beach access South Side
- Apartment rentals South Side
- Pet-friendly rentals South Side
- Rentals with outdoor seating South Side
- Rentals with a fire pit South Side
- Condo rentals South Side
- Fitness-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with pools South Side
- Rentals with lake access South Side
- Family-friendly rentals South Side
- Rentals with a fireplace South Side
- Private suite rentals South Side
- House rentals Chicago
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- House rentals United States
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Illinois Beach State Park
- Washington Park Zoo
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Raging Waves Waterpark
- The Beverly Country Club
- The 606