Condo vacation rentals in South Side
Find and book unique condos on Airbnb
Top-rated condo rentals in South Side
Guests agree: these condos are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side condo rentals
Weekly condo rentals
Condo in Chicago
4.87 out of 5 average rating, 111 reviewsSpacious Duplex in Great Location
Condo in Chinatown
4.83 out of 5 average rating, 163 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
Condo in Chicago
4.9 out of 5 average rating, 139 reviewsEast Garfield Park 2 Bedroom
Condo in Chicago
4.9 out of 5 average rating, 159 reviewsThe Bright Retreat in Andersonville
Condo in Chicago
4.96 out of 5 average rating, 112 reviewsCHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Condo in Chicago
4.98 out of 5 average rating, 211 reviewsNear Lake Michigan & Wrigley Field
Condo in Oak Park
4.96 out of 5 average rating, 133 reviewsPicture Perfect 3Bed Steps from Train and FLW
Condo in Chicago
4.94 out of 5 average rating, 178 reviewsCharming Chinatown Home by McCormick★Downtown
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 573 reviewsSpacious Evanston Unit - Walk to Northwestern U
Condo in Chicago
4.99 out of 5 average rating, 222 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Condo in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Condo in Chicago
4.83 out of 5 average rating, 313 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Chicago
4.78 out of 5 average rating, 203 reviewsModern Luxury In Old Town - Sleeps 4
Condo in The Loop
4.8 out of 5 average rating, 172 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Condo in Chicago
4.82 out of 5 average rating, 119 reviewsCharming Condo near U.C./Loop/McCormick Place
Condo in Chicago
4.82 out of 5 average rating, 190 reviewsChicago River West 4 Bedroom / 3 Bathroom
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 152 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Evanston
4.91 out of 5 average rating, 105 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Lisle
4.92 out of 5 average rating, 49 reviewsPeaceful Condo in Lisle, Illinois
Condo in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
Condo in Lombard
4.84 out of 5 average rating, 45 reviewsSmoke & Pet Free, Washer Dryer, Fireplace, Balcony
Condo in Chicago
4.8 out of 5 average rating, 20 reviewsLovely condo studio
Condo in Chicago
4.68 out of 5 average rating, 28 reviews1 bedroom in the heart of downtown Chicago.
Room in Naperville
4.5 out of 5 average rating, 6 reviewsPrivate Bedroom with Private Bath - 2nd floor
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- New Buffalo Vacation rentals
- Schaumburg Vacation rentals
- Chicago Vacation rentals
- Condo rentals Chicago
- Condo rentals Chicago
- Condo rentals Downtown Chicago
- Rentals with a washer and dryer South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with a fireplace South Side
- Private suite rentals South Side
- Family-friendly rentals South Side
- Fitness-friendly rentals South Side
- Rentals with a patio South Side
- Apartment rentals South Side
- Monthly Rentals South Side
- Smoking-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with lake access South Side
- Rentals with a hot tub South Side
- Rentals with beach access South Side
- Rentals with a fire pit South Side
- Townhouse rentals South Side
- House rentals South Side
- Rentals with pools South Side
- Waterfront rentals South Side
- Pet-friendly rentals South Side
- Kid-friendly rentals South Side
- Condo rentals Milwaukee
- Condo rentals Illinois
- Condo rentals Cook County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes