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
4.98 out of 5 average rating, 227 reviewsUkrainian Village Garden Retreat
Apartment in South Lawndale
4.93 out of 5 average rating, 115 reviewsLuxurious - 10 Minutes to Downtown Chicago - Cozy
Apartment in Chicago
4.86 out of 5 average rating, 242 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Bridgeport
4.83 out of 5 average rating, 163 reviewsChicago Vintage Home
Apartment in Oak Park
4.89 out of 5 average rating, 347 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.87 out of 5 average rating, 193 reviews2 bedroom apartment near train line and bus lines!
Apartment in Chicago
4.9 out of 5 average rating, 175 reviewsHandicap accessible apartment w/Level-2 EV Charger
Private apartment rentals
Apartment in Portage Park
4.95 out of 5 average rating, 116 reviewsComfortable, modern apartment 20 Min from Downtown
Apartment in Chicago
4.99 out of 5 average rating, 107 reviewsNewly Renovated, Spacious 2BR in Andersonville
Apartment in Kenwood
5.0 out of 5 average rating, 17 reviewsHistoric Charm Near Shops &Parks and UChicago
Apartment in Chicago
4.95 out of 5 average rating, 22 reviewsNEW Garden Unit Close to Downtown
Apartment in Chicago
4.94 out of 5 average rating, 32 reviewsTravel To Chicago New City
Apartment in Chicago
4.97 out of 5 average rating, 67 reviewsLocation! Location! Location!
Apartment in Chicago
4.91 out of 5 average rating, 74 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Apartment in Bridgeport
4.89 out of 5 average rating, 37 reviewsYour Perfect Spot :)-With Memory Foam Mattress!
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 165 reviewsSkyline Serenity: Sauna, Hot Tub, Peloton, Views
Apartment in West Town
4.88 out of 5 average rating, 402 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Apartment in Berwyn
4.91 out of 5 average rating, 209 reviews“Dream slice of urban homesteading.”
Apartment in Chicago
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Apartment in Chicago
5.0 out of 5 average rating, 10 reviewsThe Downtown Oasis (2BD / 2BA)
Apartment in Streeterville
5.0 out of 5 average rating, 12 reviewsLake, City, & River View Condo
Apartment in West Loop
New place to stayCloud9 | Co-Working+Golf|@Fulton Market |The Boho
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 United States
- Serviced apartment rentals United States
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Waterfront rentals South Side
- Condo rentals South Side
- Pet-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with a patio South Side
- Rentals with a washing machine and dryer South Side
- Fitness-friendly rentals South Side
- Rentals with outdoor seating South Side
- Townhouse rentals South Side
- Rentals with breakfast South Side
- Kid-friendly rentals South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Rentals with a fire pit South Side
- Private suite rentals South Side
- Rentals with beach access South Side
- Rentals with a fireplace South Side
- Rentals with a hot tub South Side
- Rentals with lake access South Side
- Smoking-friendly rentals South Side
- House rentals South Side
- Rentals with an EV charger 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