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
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Popular amenities for South Side apartment rentals
Weekly apartment rentals
Flat in Chicago
4.84 out of 5 average rating, 132 reviewsPerfect Private Getaway in Perfect Pilsen
Flat in Chicago
4.82 out of 5 average rating, 146 reviewsThe Posh Apt. Mins to Downtown & Hyde Park
Flat in Chicago
4.98 out of 5 average rating, 134 reviewsModern Apt with style & comfort in Pilsen Chicago
Flat in West Town
4.96 out of 5 average rating, 265 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Flat in Chicago
4.84 out of 5 average rating, 261 reviewsCharming loft style suite
Flat in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Flat in Chicago
4.89 out of 5 average rating, 107 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Flat in Chicago
4.91 out of 5 average rating, 170 reviewsHandicap accessible apartment w/Level-2 EV Charger
Private apartment rentals
Flat in Blue Island
4.93 out of 5 average rating, 266 reviewsCharming Unique 2 Bdrm Apartment in Victorian Home
Flat in Chicago
4.99 out of 5 average rating, 145 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Flat in Avondale
4.97 out of 5 average rating, 120 reviewsDesigner Avondale Attic
Flat in Chicago
4.96 out of 5 average rating, 268 reviewsCozy loft in Chicago's Uptown
Flat in Chicago
5.0 out of 5 average rating, 29 reviewsTravel To Chicago New City
Flat in Chicago
4.97 out of 5 average rating, 64 reviewsLocation! Location! Location!
Flat in Chicago
4.9 out of 5 average rating, 69 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Flat in Chicago
5.0 out of 5 average rating, 24 reviewsUrban Cottage
Apartment rentals with a hot tub
Flat in Berwyn
4.91 out of 5 average rating, 205 reviews“Dream slice of urban homesteading.”
Flat in Chicago
4.88 out of 5 average rating, 398 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Flat in West Loop
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Flat in Chicago
4.92 out of 5 average rating, 36 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Flat in The Loop
5.0 out of 5 average rating, 4 reviewsThe Playwright's Palace
Flat in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Flat in Chicago
5.0 out of 5 average rating, 11 reviewsLake, City, & River View Condo
Flat in Chicago
5.0 out of 5 average rating, 29 reviewsBelmont Pleasures - hot tub / arcade gaming room
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
- Waterfront rentals South Side
- Rentals with outdoor seating South Side
- Rentals with lake access South Side
- Rentals with a washing machine and dryer South Side
- Pet-friendly rentals South Side
- Apartment rentals South Side
- Townhouse rentals South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
- Rentals with breakfast South Side
- Rentals with a patio South Side
- Rentals with beach access South Side
- Family-friendly rentals South Side
- Rentals with a firepit South Side
- House rentals South Side
- Rentals with a hot tub South Side
- Private suite rentals South Side
- Monthly Rentals South Side
- Smoking-friendly rentals 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