Apartment vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for South Side apartment rentals
Weekly apartment rentals
Rental unit in Chicago
2 bedroom apartment near train line and bus lines!
Rental unit in Chicago
Chicago Airbnb Newly Remodeled 2-Unit Apartment!
Rental unit in Chicago
Chicago Vintage Home
Rental unit in Chicago
*Entire City Apartment 1 block to Train Park Free
Rental unit in Chicago
Handicap accessible apartment w/Level-2 EV Charger
Rental unit in Forest Park
Train ride to Chicago, welcome home
Rental unit in Chicago
Chic & Fully Furnished Studio Apt with Laundry
Rental unit in Chicago
Spacious 2BR on Quiet St - Free Park/Late Checkout
Private apartment rentals
Rental unit in Chicago
Travel To Chicago New City
Rental unit in Chicago
McCormick 2B/2Ba for up to 6 guests w Opt Parking
Rental unit in Chicago
Ground-Level Speakeasy: 1BR-1.5BA Near Everything!
Rental unit in Chicago
Stunning Basement Apartment w/free street parking!
Rental unit in Chicago
Urban Cottage
Rental unit in Chicago
Your Perfect Spot :)-With Memory Foam Mattress!
Rental unit in Chicago
Beverly Cottage Loft
Rental unit in Chicago
Location! Location! Location!
Apartment rentals with a hot tub
Rental unit in Chicago
Skyline Serenity: Sauna, Hot Tub, Peloton, Views
Rental unit in Chicago
Checkerboard Studio with Private Outdoor Hot Tub and Yard
Rental unit in Berwyn
“Dream slice of urban homesteading.”
Rental unit in Chicago
Cloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Rental unit in Chicago
Luxe Suite + Spa House Retreat! Pets Welcome
Rental unit in Chicago
Lake, City, & River View Condo
Rental unit in Chicago
Spectacular Rooftop Getaway in Heart of City
Rental unit in Chicago
The Areal Oasis
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
- Serviced apartment rentals United States
- Apartment rentals United States
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Family-friendly rentals South Side
- Rentals with a washer and dryer South Side
- Private suite rentals South Side
- Rentals with lake access South Side
- Condo rentals South Side
- Waterfront rentals South Side
- Rentals with a patio South Side
- Rentals with outdoor seating South Side
- Rentals with breakfast South Side
- Rentals with a fire pit South Side
- Rentals with beach access South Side
- Smoking-friendly rentals South Side
- Pet-friendly rentals South Side
- Rentals with a fireplace South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Kid-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a hot tub South Side
- Townhouse rentals South Side
- Fitness-friendly rentals South Side
- House rentals South Side
- Apartment rentals Milwaukee
- Apartment rentals Illinois
- Apartment 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