Kid-friendly holiday rentals in Naperville

4.99 out of 5 average rating, 103 reviews

Lincoln Park Charm + On site Parking Included!

ForrestRating, 5 stars1 month ago

A great place for our family of 4 for a week-long stay. Location was great - very walkable, quiet street, easy onsite parking, close to lots of good restaurants and the L (but not too close). Condo was clean and as expected from the description. Would stay again!

4.98 out of 5 average rating, 235 reviews

Lincoln Pk-Kingbed-fast WIFI-Parking-crib-roofdeck

AnneRating, 5 stars2 days ago

We loved everything about that apartment. Great neighbourhood, easy to get around, shops and restaurants nearby - amazing. The place itself is beautiful - very clean and friendly. We liked the beds…very comfortable mattresses. If I ever come back to Chicago I would choose the same apartment..no question!

4.91 out of 5 average rating, 123 reviews

Home in Homewood

Peaceful & Private Hot Tub Vacation Home Getaway

YoshiRating, 5 stars1 month ago

This small quaint home packs a HUGE punch when it comes to amenities and that home away from home feel. We couldn't have asked for more in an airbnb during our stay in the Chicago area. From the kuerig, to the decor, to the hot tub to the amazing bathroom and shower, this Airbnb had everything we needed and everything we didn't even know we wanted. I would HIGHLY recommend this airbnb along with the amazing and attentive hosts to anyone traveling through the area.

4.96 out of 5 average rating, 110 reviews

Home in Elmhurst

Elmhurst NEW - Super Clean Modern Farmhouse!

AndrésRating, 5 stars2 weeks ago

Incredible place to stay. Cherrie was very helpful throughout our stay and cannot recommend this place enough. It’s super peaceful and private. It’s a 25 minute drive to Chicago and other surroundings. Beds are very comfortable. Kitchen is a dream to use. Will definitely come back another time.

Apartment in Logan Square

4.95 out of 5 average rating, 693 reviews

Best in Chicago, private, amazing garden space

NatalieRating, 5 stars1 month ago

Meighan's apartment is cute and thoughtfully, stylishly laid out. From the living room, bedrooms, bathroom, kitchen/dining area, and lovely shared garden area, this was a really lovely space that was walkable, very homey, and refreshing. I commuted to downtown each day, and the walk to take the blue line was easy and close by. Meighan's bulletin board recommendations for nearby restaurants was great. I was able to find and use the 606 jogging path nearby thanks to a bulletin board brochure. Meighan was kind and welcoming to my dogs and me and it was so great to be able to bring them with me. Meighan responded quickly to my texts. Meighan provides a filtered water pitcher in the refrigerator which I recommend using for you and your pets. My dog got the runs a few days into our stay and he has a sensitive stomach when it comes to water and old pipes. As soon as I started giving my dog filtered water his issues cleared up immediately, which also alerted me to drink the filtered water.

4.83 out of 5 average rating, 339 reviews

Condo in Wicker Park

Lively Wicker Park 2br, Steps to Damen Blue Line

AmberRating, 5 stars1 month ago

Great place with a great location, central to all things in Wicker Park and Bucktown. Easy to get downtown via the blue line and walkable to all bus stops. Matched the photos and description and Vanessa and Charlie were very communicative and helpful.

Apartment in Lincoln Square

4.96 out of 5 average rating, 369 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

TannerRating, 5 stars3 days ago

Marla & James were incredible hosts! We had an absolutely great time - the neighborhood and airbnb space were perfect for our family of a toddler and two dogs we brought with us. James and Marla had plenty of games and accommodations for our toddler that he really enjoyed the space as well! Thanks again you two!

Guest suite in Naperville

4.95 out of 5 average rating, 414 reviews

Cozy Lakeview Studio with Private Access

YuRating, 5 stars6 days ago

Thank you so much for the wonderful stay! I was so glad to have chosen your place! Also, it was wonderful meeting you all! I had a nice time chatting with you! I hope to be back with my husband next! Happy Spring! Thanks, again!

4.83 out of 5 average rating, 178 reviews

Apartment in Evanston

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

SkylarRating, 5 stars3 weeks ago

Craig was extremely nice and accommodating when it came to my birthday weekend. He responds quickly to all questions asked and makes sure we’re comfortable at all times. This home was clean, accurately described, and had the perfect “home feeling”. Overall, when visiting the area I will be booking here again !

Holiday rentals for every style

Get the amount of space that is right for you

Houses

A space that's all yours, with room for everyone

Apartments

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Popular amenities for Naperville kid-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Child-friendly house rentals

4.77 out of 5 average rating, 26 reviews

Home in Roselle

Game Room | Fire Pit | Full Gym

AlexandraRating, 5 stars3 days ago

Great stay. Was perfect for our 4 adults and 2 kids

4.89 out of 5 average rating, 132 reviews

Home in Lombard

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.

4.93 out of 5 average rating, 153 reviews

Home in Lake View

Superhost Wrigley/Lakeview Duplex 3BR/2.5BA

JulietRating, 5 stars6 months ago

Lovely place in a good location.

4.83 out of 5 average rating, 65 reviews

Home in Aurora

Family home on fescue

Dee DeeRating, 5 stars1 month ago

We loved it and we come to Aurora a few times a year. We will definitely be staying again.

5 out of 5 average rating, 22 reviews

Home in Elgin

Little Blue House

BriannaRating, 5 stars4 months ago

Alex is a great host! Dog friendly places are hard to find and his place made my dog feel super comfortable. Love this place and definitely will be back.

4.87 out of 5 average rating, 45 reviews

Home in Gary

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!!

5 out of 5 average rating, 22 reviews

Home in Aurora

Evergreen Retreat

LoreineRating, 5 stars1 week ago

This is a very beautiful house with TONS of space, big and perfect for my healing retreat, I hosted 9 ladies, the backyard is huge plus there was an outdoor event area. The place looked exactly like pictures, clean, host was responsive and polite. The house is very relaxing and peaceful. I would definitely recommend!

5 out of 5 average rating, 3 reviews

Home in Homer Glen

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.

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Kid-Friendly apartment rentals

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!

4.95 out of 5 average rating, 187 reviews

Apartment in Austin

Flexible Apt. for 8 by Oak Park-CHI

WeikunRating, 5 stars3 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!

Apartment in Lincoln Square

4.79 out of 5 average rating, 295 reviews

Cozy Garden-Subterranean Apartment

NikkiRating, 5 stars3 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!

4.83 out of 5 average rating, 295 reviews

Archways at the Lincoln Park Zoo 2bed/2ba

CatherineRating, 5 stars3 days ago

Jessica’s place was great and perfect jumping off point for my family attending my brother’s wedding and other festivities.

4.95 out of 5 average rating, 203 reviews

Apartment in Joliet

*The Belltower Haven*Large*Family Friendly*Wi-Fi

RockyRating, 5 stars3 days ago

Great spot to stay and James was awesome, would highly recommend this place to any of my friends, thanks again!

4.83 out of 5 average rating, 123 reviews

Apartment in Hyde Park

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. 😁

4.85 out of 5 average rating, 248 reviews

Apartment in Evanston

Adorable 1BR apartment near Northwestern

TaraRating, 5 stars1 week ago

Nice place to stay in a good neighborhood! Would stay here again, thank you!

Apartment in Logan Square

4.95 out of 5 average rating, 509 reviews

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

KathlynRating, 5 stars1 week ago

Thank you for sharing your wonderful space. It was perfect to spend time as a family while moving our daughter in Logan Square. The park nearby was so easy to manage for our dog who joined us. Paul was responsive and helpful. Got to meet his pup who was adorable. Will definitely stay here again

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Child-Friendly Holiday Condos

4.95 out of 5 average rating, 128 reviews

Condo in Bridgeport

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.

4.89 out of 5 average rating, 112 reviews

Condo in Bridgeport

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

4.83 out of 5 average rating, 343 reviews

Condo in Wrigleyville

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.

4.99 out of 5 average rating, 134 reviews

Condo in River North

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

JoelRating, 5 stars6 days 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!

4.92 out of 5 average rating, 120 reviews

Condo in Chinatown

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

TehranRating, 5 stars1 month ago

Very great for a large group.

4.83 out of 5 average rating, 137 reviews

Condo in Pullman

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

4.88 out of 5 average rating, 206 reviews

Condo in Mount Prospect

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.