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
Flat in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Flat in Chicago
4.87 out of 5 average rating, 190 reviews2 bedroom apartment near train line and bus lines!
Flat in Portage Park
4.96 out of 5 average rating, 114 reviewsComfortable, modern apartment 20 Min from Downtown
Flat in Bridgeport
4.83 out of 5 average rating, 163 reviewsChicago Vintage Home
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Flat in Chicago
4.9 out of 5 average rating, 173 reviewsHandicap accessible apartment w/Level-2 EV Charger
Flat in Chicago
4.99 out of 5 average rating, 147 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Flat in McKinley Park
4.84 out of 5 average rating, 262 reviewsCharming loft style suite
Private apartment rentals
Flat in Chicago
4.97 out of 5 average rating, 67 reviewsLocation! Location! Location!
Flat in Chicago
4.97 out of 5 average rating, 30 reviewsTravel To Chicago New City
Flat in Bridgeport
4.89 out of 5 average rating, 36 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
Flat in Bridgeport
5.0 out of 5 average rating, 27 reviewsUrban Cottage
Flat in Chicago
4.9 out of 5 average rating, 73 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Flat in Chicago
4.93 out of 5 average rating, 54 reviewsStunning Basement Apartment w/free street parking!
Flat in Chicago
4.83 out of 5 average rating, 6 reviewsChic & Cozy, New Build 2beds, 15mins from The Bean
Flat in East Side
4.85 out of 5 average rating, 67 reviewsLovely 1-BR Apt with full kitchen & living room
Apartment rentals with a hot tub
Flat in Chicago
4.87 out of 5 average rating, 163 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Flat in West Town
4.88 out of 5 average rating, 399 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in Berwyn
4.91 out of 5 average rating, 208 reviews“Dream slice of urban homesteading.”
Flat in Chicago
4.87 out of 5 average rating, 107 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Logan Square
4.92 out of 5 average rating, 37 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Flat in The Loop
4.8 out of 5 average rating, 10 reviewsThe Areal Oasis
Flat in Chicago
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
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
- Serviced apartment rentals United States
- Flat rentals United States
- Flat rentals Chicago
- Flat rentals Chicago
- Flat rentals Downtown Chicago
- Rentals with a washing machine and dryer South Side
- Rentals with lake access South Side
- Apartment rentals South Side
- Rentals with outdoor seating South Side
- Smoking-friendly rentals South Side
- Private suite rentals South Side
- Rentals with a patio South Side
- Rentals with breakfast South Side
- Rentals with a hot tub South Side
- Fitness-friendly rentals South Side
- Rentals with a firepit South Side
- Waterfront rentals South Side
- House rentals South Side
- Rentals with beach access South Side
- Pet-friendly rentals South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Townhouse rentals South Side
- Rentals with a fireplace South Side
- Family-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Flat rentals Milwaukee
- Flat rentals Illinois
- Flat 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