
Kid-friendly vacation rentals in South Side
Find and book unique kid-friendly rentals on Airbnb
Top-rated kid-friendly rentals in South Side
Guests agree: these kid-friendly rentals 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 kid-friendly rentals
Kid-friendly house rentals

Game Room | Fire Pit | Full Gym
Great stay. Was perfect for our 4 adults and 2 kids

Comfy Home w Access to Major Roads/Hwys, Huge Yard
Great place to Spend the night or even a week. Our fight to Miami got canceled and his place was the perfect place for our family of 5 to spend the night. Friendly and responsive would definitely recommend to anyone looking for a place to stay in Chicago.

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
Lovely place in a good location.

Bliss in Brookfield- 5BR, 3BA
Nice to have a spacious place to stay with family. Our toddlers were in heaven in the basement toy/family room. Bedrooms and closets were spacious as well. Communication with host was easy with prompt responses. We would stay at this property again.

The Blue House: Family Retreat
Clean and kid friendly! Just as described. Perfect place to hang our Easter vacation with our group of 13!! Everyone felt comfortable and accommodated. Only thing I’d change if I could, more pillows! We’re a pillow loving family. Otherwise everything was great!!

Rivera House-fun and comfort steps from the beach
We had an absolutely lovely time! We took a family trip and the house was perfect for 6 adults and 5 kids. The beach was super close to walk to. The large house was perfect for everyone to have their own space. The spacious living room/kitchen was a great place to spend family time cooking, playing games, eating, etc where we could all be together but doing separate things. There were plenty of towels for everyone for that many days which surprised me! Inga had thought of everything! There was all the extras you might need too like cooking basics, sunscreen, flashlight, bug spray, beach chairs, toys, umbrellas! And the espresso machine was also a hit with our family! Thank you so much Inga for having us!! We made memories that will last a lifetime in your beautiful home!

Cozy 2 bedroom home in a wonderful neighborhood.
I think this was my fav Airbnb yet. Convenient, very clean and a great kitchen! My dog enjoyed the backyard and the neighborhood was nice. I misplaced the house keys and Joanna responded immediately and had a solution! Thank you so much for that!!!! Would love to stay again when we visit family next year.

4 bedroom home rental in quiet neighborhood
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.
Family-friendly apartment rentals

The Biddle House (#1)
We really enjoyed staying at this place - it was clean and comfortable, and the location is fantastic. Elizabeth was very responsive and a great host. We would stay here again!

Flexible Apt. for 8 by Oak Park-CHI
We had a wonderful stay! Lois was very responsive and made everything easy from start to finish. The house was cozy, clean, and well-equipped with everything we needed. Parking was super convenient, and the neighborhood felt safe and quiet. It was a perfect spot to relax after a day out. Highly recommend!

Cozy Garden-Subterranean Apartment
This is the perfect place for a cozy Chicago getaway, very clean, peaceful, great location, and probably the most well-stocked Airbnb I’ve ever stayed in. Jenny is very friendly and responsive. I would stay here again in a heartbeat!

Family Friendly 3BR Duplex in Roscoe Village
It was really good. It's an older building so it had old-building problems (creeky floors kinda thing). Other than that it was perfect for our family of four: enough room to do our own thing, enough room to be together.

Archways at the Lincoln Park Zoo 2bed/2ba
Jessica’s place was great and perfect jumping off point for my family attending my brother’s wedding and other festivities.

Vintage sunlit 2.5 BR apt. Perfect for families!
I enjoyed my stay at Letitia's place. I was traveling between the city and northern burbs, and Letitia's place provided a nice centralized location with easy access to both. Letitia's place is clean, charming, and comfortable. Letitia responded quickly to any questions. I recommend this as a comfortable place to explore the greater Chicagoland area.

Garden Apartment in captivating Hyde Park
Nice location with nearby supermarket, cafes and restaurants. The nearby busstop to go downtown is also very nice and near. Great apartment with all the necessary amenities for short stay. 😁

Adorable 1BR apartment near Northwestern
Nice place to stay in a good neighborhood! Would stay here again, thank you!
Family-friendly condo rentals

Evergreen Park Condo with balcony and Jacuzzi tub
Nice. Clean. Responsive host.

Entire 3Bed/2Bath Condo Near McCormick & Metro
We enjoyed our stay. John works hard to offer the best experience to his guests. The place was super clean and welcoming. Photos are matching. Close to everything with UBER. Some restaurants are located in the block. I recommend this appartement.

Convenient & Spacious 3BR Condo w/Free Parking
Convenient stay right outside of the heart of downtown Chicago! Easy to drive into town for the day. Very comfortable beds and very clean as well. Would recommend

Dream Condo steps from Wrigley Field!
I would definitely stay here again! Walking distance from Wrigleyville bars, restaurants and stadium. Comfortable, clean and quiet.

Luxurious River North 3BR/2BA- Free Onsite Parking
Neel went above and beyond for my family and I during our stay. The unit was quiet, fun to hang out in, extremely clean, great layout for a family, very convenient parking, and quiet. I would highly recommend staying here! Thank you Neel!

1 #33 - 4 Bdrm Condo - McCormick Place, Chinatown
Very great for a large group.

Gamers Getaway 20 minutes from downtown
Loved The Space! Everything Was Perfect! Any Problems Or Any Questions Daniel Was Very Helpful! THANK YOU DANIEL

Lovely 3-bedroom condo, free parking, Unite 1
This place was awesome. Felt very homie and comfortable. I love the decor and that there was a TV in each room. This place was beautiful and i wouldn’t mind staying again.
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- West Side Vacation rentals
- North Side Vacation rentals
- South Bend Vacation rentals
- Lake Michigan Beach Vacation rentals
- South Haven Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- Michigan City Vacation rentals
- Chicago Vacation rentals
- Rentals with beach access South Side
- Rentals with a washer and dryer South Side
- Private suite rentals South Side
- Rentals with breakfast South Side
- Smoking-friendly rentals South Side
- Bed and breakfasts South Side
- Apartment rentals South Side
- Family-friendly rentals South Side
- Rentals with outdoor seating South Side
- Condo rentals South Side
- Rentals with a firepit South Side
- House rentals South Side
- Rentals with pools South Side
- Waterfront rentals South Side
- Fitness-friendly rentals South Side
- Pet-friendly rentals South Side
- Rentals with a hot tub South Side
- Rentals with a patio South Side
- Rentals with lake access South Side
- Townhouse rentals South Side
- Rentals with a fireplace South Side
- Rentals with an EV charger South Side
- Kid-friendly rentals Chicago
- Kid-friendly rentals Cook County
- Kid-friendly rentals Illinois
- Kid-friendly rentals 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
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Six Flags Great America
- 875 North Michigan Avenue
- Lincoln Park Zoo
- Museum of Science and Industry
- The Field Museum
- Wicker Park
- Chicago History Museum
- Willis Tower
- Flossmoor Golf Club
- Brookfield Zoo
- Lincoln Park
- Illinois Beach State Park
- Skokie Country Club
- Garfield Park Conservatory
- Chicago Cultural Center
- Promontory Point