
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.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for Homewood family-friendly rentals
Family-friendly home rentals with a hot tub

Lux Urban 3BR/3BA Duplex + Parking!
They were very responsive and helpful. The apartment is large and comfortable and just a few minutes walk to the blue line. They could use a fresh coat of paint but we highly recommend staying here and will again if we get a chance.

Smart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities
Excellent location, great space, responsive host.

Spacious 2bdm unit 15min to Dwtn
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!

The Lake Escape -Cozy Lakefront Cottage Valparaiso
Kim was very friendly and so easy to work with. She was quick to respond to any questions that we had. The lake house cottage was very clean and exactly as pictured. We will definitely rent with Kim again!

Restful Refuge, Hot Tub, Firepit, Dunes Nat’l Park
It was a great stay, myself and the other guests had a great time staying here. Other than a few of the beds being stiff, the rest of the amenities were great, everything worked as expected. Also a great view of the lake from the balcony!

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Great escape from hustle bustle. Hot tub was a great addition to our visit. Would recommend for small groups.

Dunes Vacation Rental
Very nice place right by the Indian Dunes; property is very nice with lots of great landscaping, outdoor furniture and open spaces. Outside had a large 8+ person hot tub, grill, upscale fire pit, nice landscaping/frog ponds, and lots of deck space/lawn space. House itself was very well appointed and clean -- worked great for our group (6 adults, 8 kids). Mark was quick to respond whenever we reached out.

Urban Luxury 1BR/2BA Logan Square Condo w/Garage
Bryan and Barb are extremely attentive hosts. We were greeted at check in and shown throughout the apartment. Whenever we had a question or needed something Bryan was quick with a response. Their apartment is beautiful, comfortable, and fully outfitted. We immediately felt at home. It was a pleasurable, short stroll to the many wonderful restaurants Logan Square has to offer. We both would love to stay with Bryan and Barb in future trips to Chicago.
Family- and pet-friendly home rentals

Sunny Logan Square Artists' home
This listing was all that the hosts described it to be. Lots of natural light, comfortable Chicago living, and close to transport for quick access to downtown. The hosts were responsive and answered a few messages I had promptly throughout my stay. I’d recommend this place to anyone looking to visit the Chicago area and wanting to distance themselves from the middle of downtown, as well as those looking to be close to downtown but wanting to avoid the prices that come with rentals closer to the city (my situation).

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
Our stay at Jaime's place was perfect. We worked a convention at Donald E. Stephen's convention center and it was about 15 minutes from there, which was perfect. we felt right at home and Jaime showed us around the place, eventhough we got there late. The bed in the master bedroom is so comfortable, I didn't want to get up from it 🤣🤣 I loved the window in the shower. She gave us a lovely recommendation for breakfast that we loved. I would definitely stay here again.

Downtown Elegance ✨ Private Yard Parking
This home in Chicago was exactly as advertised. Perfect for a girl's weekend in Chicago. Plenty of space for sleeping, large bathrooms with plenty of mirrors to get ready. The house was well stocked with everything we needed for a perfect weekend. The location was great too. was able to walk to bars and restaurants or take short Uber anywhere we needed to go. Having off street parking made it even better for out of towners who drove to the destination. I would definitely book again when traveling with a large group.

Andersonville Living
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.

a SIMPLE place
Had a great stay at Steve's place with my friend and our 2 dogs. Nice quiet neighborhood.

2nd floor of 1908 brick two-flat in Logan Square
The location is really well suited for walking around the Logan Square neighborhood. The apartment was very clean and exactly as you see in photos. It’s right by a park too if you happen to have a dog. The hosts did a great job with communicating instructions (they also have the cutest pup). Overall I would highly recommend a stay here if you’re looking for a nice and traditional Chicago brownstone Airbnb.

Stylish Chicago Apartment near Public Transit
Afsha’s place was a great base for our family trip to Chicago. The home is clean and well maintained. The off-street paring spot is a great bonus. Afsha is a great communicator and host. We hope to stay again on a future visit.

Miller Mermaid Suite-100 yds from the beach!
I can’t say more about this great find! Location is amazing and Jennifer and Garry are wonderful. We look forward to returning!
Family-friendly home rentals with a pool

Beach Walk w/ Pond Views. Steps to Beach & Pool
Beautiful home! It had enough private bedrooms with bathrooms for our family of 9. We were within walking distance of the beach & Raychel had chairs, towels and even wagons for our use! It was quiet & secure. This was a perfect place for our family getaway together!

Beautiful Historic Colonial
Great weekend for our 25th reunion. We were 8 adults. Enjoyed the spacious dining room. Kitchen was well stocked. We hope to spend our next reunion weekend back at the house!

Dog Friendly Golf Cart included in Beachwalk w/ Po
Loved it! Awesome for kids and adults. Location is awesome and the house is beautiful.

Stylish Corner 2 Bedroom in the Heart of Chicago |
We loved our stay here! The apartment is much more spacious than we were expecting and there was more than enough storage space for our luggage. We were disappointed a bit at the poor quality of the beds but appreciated the thoughtfulness of the noise machines to aid in good sleep in the middle of the city. We would absolutely stay here again!

Beachwalk Resort - Kid Friendly w/ FREE Golf Cart
Beachwalk Resort was a great place for families! The Anchor house was beautiful and although the fridge was broken, management worked to get a replacement and reimbursed us for the groceries we lost. That was the only issue we ran into! Overall, a lovely home with lots of space and an absolutely amazing kitchen. Would love to return one day!

(2025 Open!) Private Heated Pool and Pet Friendly!
We enjoyed our stay with our son and his family. The house, yard and pool were perfect for our grandson and their two dogs. The neighborhood was very quiet and walkable. Our only possible concern was the lack of communication about the lawn being mowed and the pool being serviced on the Friday of our stay. It would have been nice to know so we could have had the dogs inside before people came into the yard.

Beautiful 137 Year Old Farm Home (3night min)
Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

Pet Friendly in Beachwalk Resort - Walk to Beach,
Phenomenal option for vacation!!! Beautiful home thats 5 minute walk to a beautiful beach on Lake Michigan. Lots of things to do for family, including a pool, small lake swimming, fishing, shuttleboard, pool table, ping pong, kayacking, stand-up paddle board, movie room, basketball court and tennis court!!! I'm sure I'm missing a bunch of things. Oh and coffee shop with snacks too on the ground. The homes are beautiful and well-taken care of. Kids told me they want to come back next summer!!! Indiana Sand Dunes is also just a 15 minute drive to the east end of the national park.
Quick stats about vacation rentals that are family-friendly in Homewood
Total rentals
30 properties
Nightly prices starting at
$142 CAD before taxes and fees
Total number of reviews
810 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Shedd Aquarium
- Frank Lloyd Wright Home and Studio
- Guaranteed Rate Field
- Lincoln Park Zoo
- The Field Museum
- Raging Waves Waterpark
- Chicago History Museum
- 875 North Michigan Avenue
- Woodlands Course at Whittaker
- Skydeck Chicago
- Olympia Fields Country Club
- Splash Station
- Deep River Waterpark
- Flossmoor Golf Club
- Odyssey Fun World
- The 606
- Humboldt Park
- Black Sheep Golf Club
- The Beverly Country Club
- National Museum of Mexican Art