Family-friendly holiday rentals in Homewood

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Homewood

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

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Guest favourite

Guest suite in Wood Dale

4.9 out of 5 average rating, 459 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 .

Guest favourite

Home in Lockport

4.95 out of 5 average rating, 116 reviews

Historic Hideaway ~ Vintage 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Lockport, Chicago, Joliet, I & M Canal & "Route 66"! If you have roots in Illinois or Lockport, the Hideaway is for you! The entire upstairs 1,500 sq ft vintage 2 bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Family & Business Friendly. Private-entrance/self-check-in. *Can accommodate up to 6 guests. Extra charges apply after 2 guests. Have a 'historic' stay at the "Hideaway"

Guest favourite

Guest suite in Miller

4.96 out of 5 average rating, 337 reviews

Miller Mermaid Suite-100 yds from the beach!

100 yds from the beach, the cozy MERMAID SWEET awaits you and is well suited for a young family or 2-3 adult friends. This artsy basement open studio space includes a private entrance, kitchenette, unique art & a cozy reading/sleeping nook! Enjoy beautiful sunsets from the upstairs deck or use the sun room on rainy days. BBQ on the grill. Visit local restaurants, shops & galleries. Hike wooded trails & swim by sandy, dune-grass beaches. . House-trained dogs welcome! Sorry no cats (allergies)

Guest favourite

Cottage in Valparaiso

4.88 out of 5 average rating, 530 reviews

Flint Lake Cottage.

This is a rustic cottage with old world charm. There are 2 fireplaces,. The home sits on a hill overlooking a lake. The lake can be accessed from the back yard. - Pet free - Earth friendly cleaning products - Private beach & park access - Easy access to city center & university - One hour from downtown Chicago - National Lakeshore and Dunes State Park nearby - Local breweries & award winning restaurants - Biking & hiking trails near by - Wood fire places to enjoy in cold weather only

Superhost

Rental unit in Chicago

4.82 out of 5 average rating, 190 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

Guest favourite

Guesthouse in Chesterton

4.92 out of 5 average rating, 343 reviews

"myhathouse" detached studio downtown Chesterton

Vaulted skylights allow natural light. Ksize bed. Futon opens into a bed. (DEEP cleaned to AirBnb COVID-19 disinfectant standards) Fully stocked kitchen, sm. bathroom w/ shower. Parking ft. of house, 1.5 M from Lake Michigan Shoreline, 2 blocks to 15th St. entry to Prairie-Dune Trail. European Market (May -Oct) each Saturday downtown. Fall season drives along U.S. HW 12 & 20 for foliage Winter day hikes, x-county skis trail, shopping trips to the Michigan City Outlet mall

Guest favourite

Home in Manteno

4.97 out of 5 average rating, 255 reviews

Manteno clean 2 king beds great location!

Prior to your stay at this home a pro ozone generator will run to sterilize the home to kill viruses and bacteria.This is a recent update we have done to ensure safety in battling the coronavirus. This three bedroom two full baths duplex also has a 2 car attached garage.The open floor plan offers a very cozy feeling from the kitchen to the dining area right into the living room. The living room has a brand new 65 inch Smart TV and a beautiful electric fireplace.

Guest favourite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 317 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.

Guest favourite

Rental unit in Blue Island

4.93 out of 5 average rating, 285 reviews

Charming Unique 2 Bdrm Apartment in Victorian Home

My place is close to the excitement and culture of the beautiful city of Chicago. It is a short walk to Metra trains with a 25 minute ride downtown. You’ll love my place because of the diverse, comfortable, quiet, tree lined neighborhood where you can relax and feel secure. It is close to expressways, golf courses and a local park with walking path. The apartment is not available to guests without previous positive reviews.

Guest favourite

Condo in West Town

4.97 out of 5 average rating, 757 reviews

Great location. Free parking.

Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Guest favourite

Rental unit in Palos Hills

4.94 out of 5 average rating, 164 reviews

Aunt Linda's Apartment with a View in Palos

Sunny, quiet, modest first floor 2 bedroom apartment in owner occupied 4-Flat apartment building. It is located in the Southwest corner of Chicago’s Cook County. It will easily accommodate 4 adults and 2 children [Note: long term stays are available.] The building's eastern view overlooks the southern suburbs of Chicago Ridge, Oak Lawn and Bridgeview.

Guest favourite

Guesthouse in Oak Park

4.89 out of 5 average rating, 479 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.