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
Apartment in Humboldt Park
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
Apartment in Pilsen Historic District
4.86 out of 5 average rating, 242 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
Apartment in Chicago
4.99 out of 5 average rating, 149 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Apartment in Chicago
4.84 out of 5 average rating, 264 reviewsCharming loft style suite
Apartment in Chicago
4.87 out of 5 average rating, 193 reviews2 bedroom apartment near train line and bus lines!
Apartment in Chicago
4.83 out of 5 average rating, 163 reviewsChicago Vintage Home
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Apartment in Chicago
4.9 out of 5 average rating, 175 reviewsHandicap accessible apartment w/Level-2 EV Charger
Private apartment rentals
Apartment in Forest Park
4.98 out of 5 average rating, 292 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
Apartment in Chicago
4.95 out of 5 average rating, 116 reviewsComfortable, modern apartment 20 Min from Downtown
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
4.97 out of 5 average rating, 68 reviewsLocation! Location! Location!
Apartment in Chicago
4.94 out of 5 average rating, 32 reviewsTravel To Chicago New City
Apartment in Chicago
4.91 out of 5 average rating, 74 reviewsGround-Level Speakeasy: 1BR-1.5BA Near Everything!
Apartment in Chicago
5.0 out of 5 average rating, 8 reviewsMcCormick 2B/2Ba for up to 6 guests w Opt Parking
Apartment rentals with a hot tub
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
4.87 out of 5 average rating, 108 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Apartment in Logan Square
4.92 out of 5 average rating, 38 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Apartment in The Loop
5.0 out of 5 average rating, 10 reviewsThe Downtown Oasis (2BD / 2BA)
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, 12 reviewsLake, City, & River View Condo
Apartment in Chicago
5.0 out of 5 average rating, 35 reviewsBelmont Pleasures - hot tub / arcade gaming room
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
- Schaumburg Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Apartment rentals United States
- Serviced apartment rentals United States
- Apartment rentals Chicago
- Apartment rentals Chicago
- Apartment rentals Downtown Chicago
- Condo rentals South Side
- Rentals with a washer and dryer South Side
- Private suite rentals South Side
- Rentals with breakfast South Side
- Waterfront rentals South Side
- Rentals with lake access South Side
- Rentals with outdoor seating South Side
- Fitness-friendly rentals South Side
- Rentals with a fireplace South Side
- Townhouse rentals South Side
- Rentals with a hot tub South Side
- Pet-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with an EV charger South Side
- Rentals with a fire pit South Side
- House rentals South Side
- Kid-friendly rentals South Side
- Rentals with beach access South Side
- Monthly Rentals South Side
- Rentals with pools South Side
- Rentals with a patio South Side
- Smoking-friendly 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