Family-friendly vacation rentals in Oak Park

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Oak Park

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Wood Dale

4.9 out of 5 average rating, 427 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Oct 17 – 24

ﺩ.ﺇ440 per night

Guest favorite

Apartment in Oak Park

4.94 out of 5 average rating, 105 reviews

Eclectic Beauty *Walk to Everything*

Absolutely beautiful flat w/large rooms. Perfectly located in the center of Downtown Oak Park, just two blocks to hop on train to Chicago. The neighborhood is home to Frank Lloyd Wright Home & Studio with unique homes along tree lined streets. Tot lot and parks nearby. Oak Park offers the perfect location for business travelers and anyone visiting the City of Chicago, attending concerts, sporting events. Free street parking. Nice outdoor space w/patio and a rooftop deck/fire pit. Come enjoy!

Oct 17 – 24

ﺩ.ﺇ736 per night

Guest favorite

Apartment in Chicago

4.95 out of 5 average rating, 170 reviews

Flexible Apt. for 8 by Oak Park-CHI

Have questions? Send an "Inquiry"! I'm flexible, as is this attractively-decorated 3BR apartment with 5 separate beds* + 2 optional infant beds. With free, easy street parking included, you'll find this home base in a quiet, residential area of NW Chicago comfy, private and accessible for both business or family. *NOTE: The apartment has 5 BEDS, NOT 6! This counting error on the Airbnb platform can't be corrected. See details below and/or click on BR-2 photos to read explanatory captions.

Oct 8 – 15

ﺩ.ﺇ599 per night

Guest favorite

Home in Forest Park

4.91 out of 5 average rating, 223 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Steps from the cobblestone streets of Forest Park into our cheery bungalow, perfect for artistic souls and business travelers alike. Inside is a design savvy mix of mid-century furniture, comfy beds, and art from around the globe. Built in 1908, it boasts modern amenities you desire without sacrificing vintage charm. Minutes away from local shops, restaurants. Just off I-290, Blue Line CTA, 20. min drive to ORD, Midway & Downtown Chicago. Plus we’re dog-friendly-- bring up to 2 pups!

Jun 25 – Jul 2

ﺩ.ﺇ573 per night

Guest favorite

Apartment in Oak Park

4.94 out of 5 average rating, 157 reviews

A quiet stay while you are away

Welcome to our cozy and comfortable home located in a quiet neighborhood. Our space is perfect for couples, solo travelers, small families, and long-term stays. This is a beautiful, modernist home located in the Frank Lloyd Wright district neighborhood, a designated historic district known for its collection of homes designed by the famous architect Frank Lloyd Wright. This district features a collection of some of his iconic designs and is a destination for architecture enthusiasts.

Dec 31 – Jan 7

ﺩ.ﺇ545 per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 293 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Apr 16 – 23

ﺩ.ﺇ357 per night

Guest favorite

Condo in Oak Park

4.88 out of 5 average rating, 163 reviews

Attractive Flat - Historic Oak Park

Attractive One Bedroom Flat for Rent in Historic Downtown Oak Park. Truly - one of the Best Locations in all of Chicago. Two Blocks from the Epicenter of this lovely city. Easy Access to Public Transportation to Downtown Chicago or the Greater Metro Area. The Elevated train -and- the Metra Train (15 Minutes by Train to Downtown) are each a quick walk. See “ property description “ For Important information for all perspective Guests:

Sep 15 – 22

ﺩ.ﺇ498 per night

Superhost

Apartment in Forest Park

4.92 out of 5 average rating, 112 reviews

Village Cottage - Forest Park Studio Pets 72142F

Welcome to Guest Nest Furnished Stays where you can "Stay Like a Local"! We offer furnished neighborhood lodging in walkable, livable areas in the near-west suburbs of Chicago. We own and manage these small, vintage-boutique apartment buildings and convert some or all of our units to furnished apartments available for extended stays. We specialize in offering fully furnished, stylish, and comfortable neighborhood stays.

May 7 – 14

ﺩ.ﺇ422 per night

Superhost

Condo in Oak Park

4.79 out of 5 average rating, 308 reviews

Peaceful Oak Park Condo Next to Green Line Metro

Very private, quiet space amidst the activity of Downtown Oak Park. The layout of the space is ideal, as bedrooms are at one end, and the living space is at the other. Private outdoor deck. Oak Park is a beautiful neighborhood full of great places to eat, drink, and shop. Metro and Green line is steps away which means access to anywhere in the city of Chicago. Private parking too!

Oct 13 – 20

ﺩ.ﺇ604 per night

Guest favorite

Apartment in Forest Park

4.83 out of 5 average rating, 162 reviews

Cozy & Convenient Oak Park w Parking / Transit

This apartment has been tailored to accommodate your stay. It is spacious, fully equipped for your everyday needs. The apartment is safe, private and very comfy! The apartment has a terrific backyard with lawn furniture for enjoying the outdoors. You can get to downtown/Chicago Loop in less than 25 minutes. Forest Park is located just outside the city of Chicago.

Jun 10 – 17

ﺩ.ﺇ386 per night

Guest favorite

Guesthouse in Oak Park

4.88 out of 5 average rating, 456 reviews

Coachhouse in central OP 4 blk to L

Just updated, furnished 1 BR 1 BA apt in Frank Lloyd Wright Historic District. Parking, kitchen, washer/dryer in unit, Air/Heat, Smart TV. Free wifi. Central location: 1 blk to farmers market, near Hemingway / Frank Lloyd Wright attractions. 4 blocks to green line. 20 min ride to downtown Chicago. Available for longer term stays.

Oct 23 – 30

ﺩ.ﺇ600 per night

Guest favorite

Apartment in Oak Park

4.91 out of 5 average rating, 171 reviews

Large sunny 3BR apt. in downtown Oak Park

Our comfortable second floor apartment is sunny, clean, spacious, and professionally decorated. Perfectly located to walk to all that Oak Park offers, or jump on the train for a 25 min ride to downtown Chicago. Two blocks from the best shopping, parks and restaurants, as well as the Frank Lloyd Wright district.

Jan 14 – 21

ﺩ.ﺇ758 per night