Apartment holiday rentals in South Side
Find and book unique apartments on Airbnb
Top-rated apartment rentals in South Side
Guests agree: these apartments 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 apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.99 out of 5 average rating, 567 reviewsUrban Comfort in the Heart of Chicago
Apartment in Chicago
4.91 out of 5 average rating, 233 reviewsModern/Spacious 2BR/2BA West Town
Apartment in Chicago
4.98 out of 5 average rating, 205 reviewsNear Lake Michigan & Wrigley Field
Apartment in Chicago
4.9 out of 5 average rating, 137 reviewsEast Garfield Park 2 Bedroom
Apartment in Chicago
4.81 out of 5 average rating, 445 reviewsCozy Apartment with Free On-Site Parking
Apartment in Chicago
5.0 out of 5 average rating, 102 reviewsSpacious 4 Bedroom Condo
Apartment in Chicago
4.96 out of 5 average rating, 127 reviewsEast Lakeview Designer Condo with 2 Bd, 2 Bath
Apartment in Chicago
4.93 out of 5 average rating, 218 reviewsThe Upscale Getaway Near Downtown
Pet-friendly apartment rentals
Apartment in Evanston
4.77 out of 5 average rating, 569 reviewsSpacious Evanston Unit - Walk to Northwestern U
Apartment in Chicago
4.99 out of 5 average rating, 186 reviewsPets OK | Walk Score 95 | Desk | 1,750ft² |W/D
Apartment in Chicago
4.93 out of 5 average rating, 188 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Apartment in Chicago
4.94 out of 5 average rating, 111 reviewsClifton Garden Oasis 1 Min Walk to Wrigley
Apartment in Chicago
4.82 out of 5 average rating, 118 reviewsCharming Condo near U.C./Loop/McCormick Place
Apartment in Chicago
4.83 out of 5 average rating, 310 reviewsChic and Charming Vintage Condominium in Lincoln Park
Apartment in Chicago
4.78 out of 5 average rating, 202 reviewsModern Luxury In Old Town - Sleeps 4
Apartment in The Loop
4.8 out of 5 average rating, 170 reviewsMICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba
Apartment rentals with a pool
Apartment in Chicago
4.74 out of 5 average rating, 148 reviewsCentral Downtown Location-Modern 2BR Condo
Apartment in Evanston
4.91 out of 5 average rating, 103 reviewsChicago's Treasure "Heart of Evanston" 2bdr +1 Ba
Apartment in Portage
4.93 out of 5 average rating, 81 reviewsCozy 1 bedroom condo on Marina near Lake Michigan
Apartment in Lisle
4.96 out of 5 average rating, 45 reviewsPeaceful Condo in Lisle, Illinois
Apartment in Portage
4.93 out of 5 average rating, 69 reviewsUnsalted Stay - Waterfront Condo
Apartment in Portage
5.0 out of 5 average rating, 55 reviewsLuxury Waterfront 2 Bedroom Condo by Lake Michigan
Apartment in Elk Grove Village
4.95 out of 5 average rating, 56 reviewsJust remodeled apartment close to airport and mall
Apartment 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
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Townhouse rentals South Side
- Rentals with breakfast South Side
- Pet-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with lake access South Side
- Family-friendly rentals South Side
- House rentals South Side
- Rentals with a washing machine and dryer South Side
- Flat rentals South Side
- Private suite rentals South Side
- Rentals with a hot tub South Side
- Rentals with a firepit South Side
- Rentals with a patio South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
- Rentals with beach access South Side
- Monthly Rentals South Side
- Family-friendly rentals South Side
- Waterfront rentals South Side
- Rentals with outdoor seating South Side
- Smoking-friendly rentals South Side
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Apartment 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