Condo holiday 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.
Holiday 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
4.82 out of 5 average rating, 126 reviews-CHICAGO STUDIO IN JEFFERSON PARK O'HARE ROSEMONT-
Condo in Chinatown
4.83 out of 5 average rating, 160 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
Condo in Oak Park
4.88 out of 5 average rating, 164 reviewsAttractive Flat - Historic Oak Park
Condo in Chicago
4.93 out of 5 average rating, 190 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Condo in Chicago
4.81 out of 5 average rating, 446 reviewsCozy Apartment with Free On-Site Parking
Condo in Chicago
4.98 out of 5 average rating, 209 reviewsNear Lake Michigan & Wrigley Field
Condo in Chicago
5.0 out of 5 average rating, 106 reviewsSpacious 4 Bedroom Condo
Condo in Chicago
4.88 out of 5 average rating, 236 reviews2 King Bed Condo Easy Downtown Free Street Parking
Pet-friendly condo rentals
Condo in Evanston
4.77 out of 5 average rating, 570 reviewsSpacious Evanston Unit - Walk to Northwestern U
Condo in Chicago
4.99 out of 5 average rating, 193 reviewsPets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Condo in Chicago
4.83 out of 5 average rating, 311 reviewsChic and Charming Vintage Condominium in Lincoln Park
Condo in Chicago
4.78 out of 5 average rating, 202 reviewsModern Luxury In Old Town - Sleeps 4
Condo in Chicago
4.82 out of 5 average rating, 118 reviewsCharming Condo near U.C./Loop/McCormick Place
Condo in The Loop
4.8 out of 5 average rating, 171 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Condo in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Condo in Chicago
4.91 out of 5 average rating, 303 reviewsSusie's Space. 2BR easy parking & pet friendly
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 150 reviewsCentral Downtown Location-Modern 2BR Condo
Condo in Evanston
4.91 out of 5 average rating, 104 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Condo in Portage
4.93 out of 5 average rating, 81 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Condo in Lisle
4.96 out of 5 average rating, 45 reviewsPeaceful Condo in Lisle, Illinois
Condo in Portage
5.0 out of 5 average rating, 55 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Condo in Portage
4.93 out of 5 average rating, 69 reviewsUnsalted Stay - Waterfront Condo
Condo in Elk Grove Village
4.95 out of 5 average rating, 57 reviewsJust remodeled apartment close to airport and mall
Condo in Portage
4.92 out of 5 average rating, 24 reviewsSerenity on the Shores
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Schaumburg Holiday rentals
- Chicago Holiday rentals
- Condo rentals Chicago
- Condo rentals Chicago
- Condo rentals Downtown Chicago
- Rentals with a fireplace South Side
- Rentals with lake access South Side
- Apartment rentals South Side
- Family-friendly rentals South Side
- Rentals with outdoor seating South Side
- Private suite rentals South Side
- Rentals with breakfast South Side
- Rentals with a washing machine and dryer South Side
- Kid-friendly rentals South Side
- Smoking-friendly rentals South Side
- Monthly Rentals South Side
- Rentals with a patio South Side
- Fitness-friendly rentals South Side
- Rentals with a hot tub South Side
- Waterfront rentals South Side
- House rentals South Side
- Pet-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with beach access South Side
- Townhouse rentals South Side
- Rentals with a fire pit South Side
- Rentals with pools South Side
- Condo rentals Milwaukee
- Condo rentals Illinois
- Condo rentals Cook County
- 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