
Family-friendly holiday rentals in South Side
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in South Side
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for South Side family-friendly rentals
Family-friendly home rentals with a hot tub

Lux Urban 3BR/3BA Duplex + Parking!
This is our fourth time staying at this home and we love it. There is a Korean supermarket (huge) a five minute walk away from the home. There are three bedrooms and three full bathrooms which makes it easy and private for everyone. Kitchen has a lot of additional things you do not see in other homes. We love staying here.

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Great escape from hustle bustle. Hot tub was a great addition to our visit. Would recommend for small groups.

Urban Luxury 1BR/2BA Logan Square Condo w/Garage
We had an awesome and memorable experience for our christmas vacation in Chicago. Bryan was very responsive to any of our questions and was an overall great host with an awesome, super comfy place. During our stay we even had a minor appliance issue and Bryan replaced the whole thing and got it working again within the hour on a Sunday! If you stay here you definitely won't regret it!

Spacious 2bdm unit 15min to Dwtn
This place was extremely great! It was close to downtown and lots of restaurants and food near by the bnb! Only thing I’ll say is the shower head is kind of flimsy but besides that everything is nice clean and the rooms are huge! Very peaceful and quiet over there!

Dunes Nat 'l Park, HotTub, Sauna, Firepit, Foosball
Great house with lots amenities. Hilary was very responsive and accommodating.
Family- and pet-friendly home rentals

Bright Condo near the Lincoln Park Zoo
Heather was super helpful and gave great suggestions on things to do. Perfect location less than 2 miles from Wrigley Field and about 3-4 miles north of the city. Extremely walkable with local bars, restaurants, and cafes. Lincoln Park is right next door. Uber is easy and cheap. Street parking is free at this location if you can find it. We parked outside one day when a spot opened up, otherwise we parked about a block away, again super walkable! Thanks Heather for a great stay!

Sunny Logan Square Artists' home
Highly recommend booking here! Both hosts were very responsive and the space itself is beautiful. No problems whatsoever and would stay again in a heartbeat.

Insta Worthy Prime Spot *Patio *Parking *Fireplace
We had a wonderful stay with our family. The location was better than expected. Close to so many things & very walkable. Alexandria was really helpful & kept in constant contact with us. We had a wonderful stay!

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
Ms. Jamie was a great host who took us in and kicked out the Red carpet for us. My wife and I celebrated 8 years of marriage and Ms. Jamie was very welcoming and everything was in ars reach she has a great location and all the information you need for the area. This was our 1st air bnb stay and we loved it

Andersonville Living
We had a great stay! Quiet street, very easy check in and out, clean, and lots of space. Great for a family or small group of friends.

a SIMPLE place
Great stay! Steve was great and accommodating! Felt right at home!

2nd floor of 1908 brick two-flat in Logan Square
I stayed for about a week at Paul and Sarah's home and it was very pleasant. They provided very detailed instructions for check-in and I had no problems navigating to the building. The apartment itself is cozy and gets plenty of light in the daytime, though the floorboards were a bit creaky so I recommend treading lightly if you're someone with heavy footsteps. The TV also doesn't come with a streaming device so if you plan on watching Netflix/etc. be sure to bring your own device or an HDMI cable that can mirror a laptop. There was also an induction plate provided for light cooking which was helpful on the days I didn't want to do takeout. Overall this was a great home base for exploring Logan Square with very easy access to other neighborhoods/downtown via the Blue line and bus.

Stylish Chicago Apartment near Public Transit
This place was exactly what we were expecting. First and foremost, it was clean and homey. The parking space was the cherry on top and made coming and going super convenient. Afsha was a great host and did a fantastic job of communicating with us. We would absolutely recommend.
Family-friendly home rentals with a pool

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
I had an amazing stay at this place. Felt like home.The space was clean, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable visit. The host was incredibly welcoming and responsive, making sure every detail was perfect. The location was ideal, close to local attractions yet peaceful and quiet. It truly felt like a home away from home, and I can’t wait to book again for my next trip. Highly recommended!

Stylish Corner 2 Bedroom in the Heart of Chicago |
Great location great host will stay here again.

Music Hot Spot’s Main Level
Rose is a totally lovely and nice landlady. Very helpful. I felt super comfortable and taken care of during my stay with her and her family.

Luxury Corner 2 Bedroom in the Loop | Roof Deck
Loved everything about this place! The views were great! Close to so many restaurants, bars, museums, the bean and so much more. would definitly book this again. Thank you for sharing your place with our family!
Destinations to explore
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