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
4.86 out of 5 average rating, 123 reviews3D Tour! Designer Condo near Logan Square
Nov 24 – Dec 1
Condo in Little Italy
4.96 out of 5 average rating, 118 reviewsPrivate hot tub - King bed suite - Free parking
Sep 12 – 19
Condo in Chinatown
4.82 out of 5 average rating, 159 reviewsSecluded 2BR APT in Chinatown by McCormick/DWTN
Apr 10 – 17
Condo in Chicago
4.99 out of 5 average rating, 561 reviewsUrban Comfort in the Heart of Chicago
Jul 24 – 31
Condo in Chicago
4.95 out of 5 average rating, 130 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Condo in Chicago
4.81 out of 5 average rating, 444 reviewsCozy Apartment with Free On-Site Parking
Oct 1 – 8
Condo in Chicago
4.91 out of 5 average rating, 120 reviewsSpacious & Modern Family Friendly North Center Apt
Mar 8 – 15
Condo in Chicago
4.91 out of 5 average rating, 246 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Dec 20 – 27
Pet-friendly condo rentals
Condo in Evanston
4.76 out of 5 average rating, 565 reviewsSpacious Evanston Unit - Walk to Northwestern U
Oct 27 – Nov 3
Condo in Chicago
4.78 out of 5 average rating, 199 reviewsModern Luxury In Old Town - Sleeps 4
Jan 29 – Feb 5
Condo in Chicago
4.99 out of 5 average rating, 211 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
Nov 1 – 8
Condo in Portage
4.8 out of 5 average rating, 158 reviewsMarina Condo near Lake Michigan
Mar 29 – Apr 5
Condo in The Loop
4.77 out of 5 average rating, 160 reviewsSafe Dtown Park VIEWS| Mich Ave, Museums 2bd/2ba
Jun 8 – 15
Condo in Chicago
4.95 out of 5 average rating, 128 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Jan 11 – 18
Condo in Chicago
4.91 out of 5 average rating, 296 reviewsSusie's Space. 2BR easy parking & pet friendly
Jul 11 – 18
Condo rentals with a pool
Condo in Chicago
4.75 out of 5 average rating, 144 reviewsCentral Downtown Location-Modern 2BR Condo
Jun 30 – Jul 7
Condo in Evanston
4.91 out of 5 average rating, 102 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Jan 25 – Feb 1
Condo in Lisle
4.95 out of 5 average rating, 41 reviewsPeaceful Condo in Lisle, Illinois
Oct 15 – 22
Condo in Portage
4.96 out of 5 average rating, 78 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Apr 8 – 15
Condo in Portage
4.94 out of 5 average rating, 67 reviewsUnsalted Stay - Waterfront Condo
Aug 24 – 31
Condo in Portage
5.0 out of 5 average rating, 53 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Sep 15 – 22
Condo in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Nov 21 – 28
Condo in Portage
4.91 out of 5 average rating, 23 reviewsSerenity on the Shores
Sep 20 – 27
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 lake access South Side
- Smoking-friendly rentals South Side
- Rentals with a hot tub South Side
- Rentals with a fire pit South Side
- Private suite rentals South Side
- Pet-friendly rentals South Side
- Rentals with a washer and dryer South Side
- Waterfront rentals South Side
- Rentals with beach access South Side
- Monthly Rentals South Side
- Apartment rentals South Side
- Rentals with outdoor seating South Side
- Rentals with a fireplace South Side
- Kid-friendly rentals South Side
- Rentals with an EV charger South Side
- House rentals South Side
- Family-friendly rentals South Side
- Rentals with breakfast South Side
- Fitness-friendly rentals South Side
- Rentals with a patio South Side
- Townhouse 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