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Family-friendly holiday rentals in South Side

Find and book unique family-friendly homes on Airbnb

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Popular amenities for South Side family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Chicago
4.85 out of 5 average rating, 311 reviews

Lux Urban 3BR/3BA Duplex + Parking!

RobertRating, 5 stars1 month ago
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.
Home in Miller Beach
4.53 out of 5 average rating, 159 reviews

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

PamelaRating, 5 stars3 weeks ago
Great escape from hustle bustle. Hot tub was a great addition to our visit. Would recommend for small groups.
Top Guest favourite
Condo in Chicago
4.98 out of 5 average rating, 264 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

ConorRating, 5 stars2 months ago
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!
Apartment in Chicago
4.45 out of 5 average rating, 20 reviews

Spacious 2bdm unit 15min to Dwtn

Helena ORating, 5 stars2 months ago
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!
Home in Miller Beach
4.67 out of 5 average rating, 93 reviews

Dunes Nat 'l Park, HotTub, Sauna, Firepit, Foosball

Nehad Rating, 5 stars2 months ago
Great house with lots amenities. Hilary was very responsive and accommodating.

Family- and pet-friendly home rentals

Superhost
Condo in Chicago
4.75 out of 5 average rating, 99 reviews

Bright Condo near the Lincoln Park Zoo

LaurenRating, 5 stars2 months ago
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!
Guest favourite
Apartment in Chicago
4.9 out of 5 average rating, 392 reviews

Sunny Logan Square Artists' home

HannahRating, 5 stars2 weeks ago
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.
Superhost
Townhouse in Chicago
4.74 out of 5 average rating, 210 reviews

Insta Worthy Prime Spot *Patio *Parking *Fireplace

AmyRating, 5 stars2 months ago
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!
Guest favourite
Guest suite in Chicago
4.94 out of 5 average rating, 155 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

MauriceRating, 5 starstoday
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
Top Guest favourite
Apartment in Chicago
4.93 out of 5 average rating, 425 reviews

Andersonville Living

MayaRating, 5 stars2 months ago
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.
Guest favourite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 331 reviews

a SIMPLE place

JenniferRating, 5 stars3 weeks ago
Great stay! Steve was great and accommodating! Felt right at home!
Top Guest favourite
Apartment in Chicago
4.95 out of 5 average rating, 504 reviews

2nd floor of 1908 brick two-flat in Logan Square

GinaRating, 5 stars2 weeks ago
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.
Guest favourite
Apartment in Chicago
4.94 out of 5 average rating, 217 reviews

Stylish Chicago Apartment near Public Transit

JaymeRating, 5 stars3 weeks ago
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.

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