Family-friendly vacation 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 favorite

Guesthouse in Batavia

4.91 out of 5 average rating, 254 reviews

Quaint Batavia Coach House

I am creating an airbnb account for my two lovely parents, who are empty nesters for the first time in thirty-two years. We, myself and my five siblings, were blessed to be raised in the quaint city of Batavia, IL, which boasts river paths, close proximity to a train station that will take you into Chicago, and historic neighborhoods such as our own. Our property consists of two homes, our own and a coach house, which we would love for you to stay in! Both are situated on a family-friendly old-fashioned alley with mature maple trees. We thank you and wish you a pleasant stay regardless of where you choose to stay the night. All our best.

Apr 5 – 12

G$17,126 GYD per night

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

G$25,062 GYD per night

Guest favorite

Cottage in Valparaiso

4.88 out of 5 average rating, 496 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

Dec 15 – 22

G$26,787 GYD per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

Dec 9 – 16

G$20,437 GYD per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 237 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

5 Star Reviews! 1 Bedroom Apartment,King Bed, queen sofasleeper, OwnOcc. Bldg. Featuring Central Air, Private Balcony, Deluxe Kitchen Stainless Steel Appliances, Microwave, & More. 55" TV, Direct TV.This outstanding Location is steps from the Roscoe Village Business District and a quick walk to the Train Stop & Bus stops, to Downtown Chicago & United Center(Hawks & Bulls).Walk to Bars, Restaurants & Shops.All stays over 30 days will require Guests to Complete additional "Lease".,

Nov 3 – 10

G$21,850 GYD per night

Guest favorite

Guesthouse in Chesterton

4.91 out of 5 average rating, 314 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

Jul 9 – 16

G$25,083 GYD per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 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.

Feb 2 – 9

G$20,321 GYD per night

Guest favorite

Apartment in Blue Island

4.93 out of 5 average rating, 264 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.

Aug 12 – 19

G$31,200 GYD per night

Guest favorite

Guest suite in Highland Park

4.96 out of 5 average rating, 111 reviews

Charming in-law suite w/ use of deck and yard

Charming little house in Highland Park. In-law suite is in the basement and has it's own full size kitchen bathroom. We live up-stairs with our 3 little dogs so we will be available if you need anything during your stay. The in-law suite is set up like a studio and has one queen bed and a separate closet area. Please note- the suite is in the basement. You have shared use of the deck/yard

Aug 6 – 13

G$26,593 GYD per night

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 491 reviews

2BR Bursting w/ Character in Hip Logan Square!

The unit sits on our extra wide city lot in the center of hip Logan Square! The apartment is eclectic and well decorated, with vintage touches and full of charm. For a garden unit it feels spacious, clean, bright and comes with all of the desired amenities, including access to our spacious side yard!

Mar 26 – Apr 2

G$28,904 GYD per night

Guest favorite

Home in Cedar Lake

5.0 out of 5 average rating, 128 reviews

Lake front home on the hill.

Hello. Our house is available so that people can enjoy life. Fish, swim, or just hang out on the private pier, (Shared by owner). Beautiful sunsets. House has a large covered deck. Inside you will find a tastefully furnished house with all the comforts of home. TVs in all the rooms.

Aug 26 – Sep 2

G$72,676 GYD per night

Guest favorite

Guest suite in Chicago

4.91 out of 5 average rating, 419 reviews

Cozy, Quiet, Garden Getaway!

Quiet 1BD garden apartment in Northcenter/Lincoln Square. 10 minutes to the el and Lincoln Square, one of the best neighborhoods in Chicago. Full kitchen, bathroom, cable and internet. Tree lined street close to two parks and a river walk. ****WE DO NOT RENT TO FILM CREWS****

Mar 11 – 18

G$21,474 GYD per night