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 Chinatown
4.82 out of 5 average rating, 159 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
Mar 29 – Apr 5
Condo in Chicago
4.92 out of 5 average rating, 248 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Dec 6 – 13
Condo in Chicago
4.99 out of 5 average rating, 564 reviewsUrban Comfort in the Heart of Chicago
Jul 24 – 31
Condo in Chicago
4.91 out of 5 average rating, 233 reviewsModern/Spacious 2BR/2BA West Town
Apr 7 – 14
Condo in Chicago
4.86 out of 5 average rating, 437 reviewsHumboldt Park Traveler's Lodge
Jun 20 – 27
Condo in Chicago
4.9 out of 5 average rating, 168 reviews2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
Jul 11 – 18
Condo in Chicago
4.88 out of 5 average rating, 235 reviews2 King Bed Condo Easy Downtown Free Street Parking
Jan 29 – Feb 5
Condo in Chicago
4.96 out of 5 average rating, 126 reviewsEast Lakeview Designer Condo with 2 Bd, 2 Bath
Apr 26 – May 3
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 568 reviewsSpacious Evanston Unit - Walk to Northwestern U
Dec 2 – 9
Condo in Chicago
4.99 out of 5 average rating, 214 reviews❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
Mar 16 – 23
Condo in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Sep 17 – 24
Condo in Portage
4.8 out of 5 average rating, 158 reviewsMarina Condo near Lake Michigan
Feb 28 – Mar 7
Condo in Chicago
4.83 out of 5 average rating, 178 reviewsCan't Beat This 2min Walk to Wrigley!
Nov 26 – Dec 3
Condo in Chicago
4.78 out of 5 average rating, 201 reviewsModern Luxury In Old Town - Sleeps 4
Dec 11 – 18
Condo in Chicago
4.82 out of 5 average rating, 117 reviewsCharming Condo near U.C./Loop/McCormick Place
Sep 13 – 20
Condo in The Loop
4.8 out of 5 average rating, 168 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Jul 10 – 17
Condo rentals with a pool
Condo in Chicago
4.74 out of 5 average rating, 147 reviewsCentral Downtown Location-Modern 2BR Condo
Jul 4 – 11
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Dec 2 – 9
Condo in Lisle
4.95 out of 5 average rating, 43 reviewsPeaceful Condo in Lisle, Illinois
Mar 25 – Apr 1
Condo in Portage
4.96 out of 5 average rating, 78 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Mar 27 – Apr 3
Condo in Portage
4.94 out of 5 average rating, 68 reviewsUnsalted Stay - Waterfront Condo
Oct 14 – 21
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Sep 4 – 11
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Nov 23 – 30
Condo in Portage
4.91 out of 5 average rating, 23 reviewsSerenity on the Shores
Mar 18 – 25
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 breakfast South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a washer and dryer South Side
- Rentals with a fireplace South Side
- Smoking-friendly rentals South Side
- Private suite rentals South Side
- Rentals with a patio South Side
- Rentals with a hot tub South Side
- Rentals with a fire pit South Side
- Rentals with outdoor seating South Side
- Kid-friendly rentals South Side
- Rentals with beach access South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Apartment rentals South Side
- Waterfront rentals South Side
- Monthly Rentals South Side
- Rentals with lake access South Side
- Pet-friendly rentals 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