Kid-friendly vacation rentals in South Side

Find and book unique kid-friendly rentals on Airbnb

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Popular amenities for South Side kid-friendly rentals

Kid-friendly house rentals

Superhost
Home in Roselle
4.77 out of 5 average rating, 26 reviews

Game Room | Fire Pit | Full Gym

AlexandraRating, 5 stars4 days ago
Great stay. Was perfect for our 4 adults and 2 kids
Guest favourite
Home in Lombard
4.89 out of 5 average rating, 132 reviews

Comfy Home w Access to Major Roads/Hwys, Huge Yard

DanielRating, 5 stars1 month ago
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.
Top guest favourite
Home in Chicago
4.93 out of 5 average rating, 153 reviews

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars6 months ago
Lovely place in a good location.
Guest favourite
Home in Brookfield
4.93 out of 5 average rating, 27 reviews

Bliss in Brookfield- 5BR, 3BA

DeanneRating, 5 stars3 weeks ago
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.
Superhost
Home in Gary
4.87 out of 5 average rating, 45 reviews

The Blue House: Family Retreat

AlexisRating, 5 stars1 week ago
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!!
Guest favourite
Home in Gary
4.9 out of 5 average rating, 29 reviews

Rivera House-fun and comfort steps from the beach

EmilyRating, 5 stars10 months ago
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!
Guest favourite
Home in Wood Dale
4.91 out of 5 average rating, 34 reviews

Cozy 2 bedroom home in a wonderful neighborhood.

LinhRating, 5 stars5 months ago
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.
Superhost
Home in Homer Glen
5 out of 5 average rating, 3 reviews

4 bedroom home rental in quiet neighborhood

LoriRating, 5 stars71 months ago
Quiet neighborhood, spacious and comfortable home. The yard is inviting and a great entertaining space! Very kind hosts.

Family-friendly apartment rentals

Guest favourite
Apartment in Chicago
4.72 out of 5 average rating, 117 reviews

The Biddle House (#1)

SitaRating, 5 stars3 months ago
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!
Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 187 reviews

Flexible Apt. for 8 by Oak Park-CHI

WeikunRating, 5 stars4 days ago
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!
Top guest favourite
Apartment in Chicago
4.79 out of 5 average rating, 295 reviews

Cozy Garden-Subterranean Apartment

NikkiRating, 5 stars4 days ago
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!
Superhost
Apartment in Chicago
4.85 out of 5 average rating, 267 reviews

Family Friendly 3BR Duplex in Roscoe Village

KellyRating, 5 stars3 weeks ago
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.
Superhost
Apartment in Chicago
4.83 out of 5 average rating, 295 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

CatherineRating, 5 stars4 days ago
Jessica’s place was great and perfect jumping off point for my family attending my brother’s wedding and other festivities.
Guest favourite
Apartment in Evanston
4.94 out of 5 average rating, 141 reviews

Vintage sunlit 2.5 BR apt. Perfect for families!

TomRating, 5 stars4 days ago
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.
Guest favourite
Apartment in Chicago
4.83 out of 5 average rating, 123 reviews

Garden Apartment in captivating Hyde Park

ThongLengRating, 5 stars2 weeks ago
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. 😁
Guest favourite
Apartment in Evanston
4.85 out of 5 average rating, 248 reviews

Adorable 1BR apartment near Northwestern

TaraRating, 5 stars1 week ago
Nice place to stay in a good neighborhood! Would stay here again, thank you!

Family-friendly condo rentals

Superhost
Condo in Evergreen Park
4.8 out of 5 average rating, 117 reviews

Evergreen Park Condo with balcony and Jacuzzi tub

DRating, 5 stars2 months ago
Nice. Clean. Responsive host.
Guest favourite
Condo in Chicago
4.95 out of 5 average rating, 128 reviews

Entire 3Bed/2Bath Condo Near McCormick & Metro

AudreyRating, 5 stars1 week ago
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.
Guest favourite
Condo in Chicago
4.89 out of 5 average rating, 112 reviews

Convenient & Spacious 3BR Condo w/Free Parking

RachelRating, 5 stars2 weeks ago
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
Guest favourite
Condo in Chicago
4.83 out of 5 average rating, 344 reviews

Dream Condo steps from Wrigley Field!

AnitaRating, 5 stars1 week ago
I would definitely stay here again! Walking distance from Wrigleyville bars, restaurants and stadium. Comfortable, clean and quiet.
Guest favourite
Condo in Chicago
4.99 out of 5 average rating, 134 reviews

Luxurious River North 3BR/2BA- Free Onsite Parking

JoelRating, 5 stars1 week ago
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!
Guest favourite
Condo in Chicago
4.92 out of 5 average rating, 120 reviews

1 #33 - 4 Bdrm Condo - McCormick Place, Chinatown

TehranRating, 5 stars1 month ago
Very great for a large group.
Superhost
Condo in Chicago
4.83 out of 5 average rating, 137 reviews

Gamers Getaway 20 minutes from downtown

KaylinRating, 5 stars1 month ago
Loved The Space! Everything Was Perfect! Any Problems Or Any Questions Daniel Was Very Helpful! THANK YOU DANIEL
Guest favourite
Condo in Mount Prospect
4.88 out of 5 average rating, 206 reviews

Lovely 3-bedroom condo, free parking, Unite 1

MelvinaRating, 5 stars1 week ago
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.

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