Family-friendly vacation rentals in Homewood

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Homewood family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in West Town
4.85 out of 5 average rating, 312 reviews

Lux Urban 3BR/3BA Duplex + Parking!

BrentRating, 5 stars1 week ago
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.
Home in Miller
4.55 out of 5 average rating, 132 reviews

Smart Home, Hot Tub, direct Beach/Nat’l Park access, luxury amenities

TimothyRating, 5 stars2 months ago
Excellent location, great space, responsive host.
Apartment in Bronzeville
4.36 out of 5 average rating, 22 reviews

Spacious 2bdm unit 15min to Dwtn

Helena ORating, 5 stars2 months ago
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!
Guest favorite
Cottage in Valparaiso
4.93 out of 5 average rating, 409 reviews

The Lake Escape -Cozy Lakefront Cottage Valparaiso

AudreyRating, 5 stars2 weeks ago
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!
Home in Miller
4.58 out of 5 average rating, 66 reviews

Restful Refuge, Hot Tub, Firepit, Dunes Nat’l Park

SebastianRating, 5 stars3 months ago
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!
Home in Miller
4.53 out of 5 average rating, 159 reviews

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

PamelaRating, 5 stars1 month ago
Great escape from hustle bustle. Hot tub was a great addition to our visit. Would recommend for small groups.
Superhost
Home in Beverly Shores
4.91 out of 5 average rating, 133 reviews

Dunes Vacation Rental

DaveRating, 5 stars7 months ago
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.
Top guest favorite
Condo in Logan Square
4.98 out of 5 average rating, 267 reviews

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

JeanRating, 5 stars2 weeks ago
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

Guest favorite
Apartment in Logan Square
4.9 out of 5 average rating, 393 reviews

Sunny Logan Square Artists' home

TreyRating, 5 stars2 weeks ago
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).
Guest favorite
Guest suite in Portage Park
4.94 out of 5 average rating, 156 reviews

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK

HeatherRating, 5 stars5 days ago
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.
Guest favorite
Townhouse in Old Town
4.85 out of 5 average rating, 166 reviews

Downtown Elegance ✨ Private Yard Parking

NicoleRating, 5 stars1 month ago
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.
Top guest favorite
Apartment in Andersonville
4.93 out of 5 average rating, 425 reviews

Andersonville Living

MayaRating, 5 stars3 months ago
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.
Guest favorite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 334 reviews

a SIMPLE place

JulieRating, 5 stars6 days ago
Had a great stay at Steve's place with my friend and our 2 dogs. Nice quiet neighborhood.
Top guest favorite
Apartment in Logan Square
4.95 out of 5 average rating, 505 reviews

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

ChristopherRating, 5 stars4 days ago
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.
Guest favorite
Apartment in Irving Park
4.94 out of 5 average rating, 221 reviews

Stylish Chicago Apartment near Public Transit

TeakRating, 5 stars2 weeks ago
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.
Top guest favorite
Guest suite in Miller
4.96 out of 5 average rating, 351 reviews

Miller Mermaid Suite-100 yds from the beach!

NicoleRating, 5 stars6 days ago
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

Guest favorite
Cottage in Long Beach
5 out of 5 average rating, 61 reviews

Beach Walk w/ Pond Views. Steps to Beach & Pool

RebeccaRating, 5 stars7 months ago
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!
Home in Evanston
4.89 out of 5 average rating, 44 reviews

Beautiful Historic Colonial

AlexisRating, 5 stars4 months ago
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!
Home in Michigan City
4.67 out of 5 average rating, 6 reviews

Dog Friendly Golf Cart included in Beachwalk w/ Po

KyleeRating, 5 stars35 months ago
Loved it! Awesome for kids and adults. Location is awesome and the house is beautiful.
Apartment in The Loop
4.77 out of 5 average rating, 213 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

KristieRating, 5 stars1 week ago
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!
Home in Michigan City
5 out of 5 average rating, 11 reviews

Beachwalk Resort - Kid Friendly w/ FREE Golf Cart

HeatherRating, 5 stars7 months ago
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!
Superhost
Home in Michiana Shores
4.77 out of 5 average rating, 13 reviews

(2025 Open!) Private Heated Pool and Pet Friendly!

RichardRating, 5 stars19 months ago
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.
Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars7 months ago
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!
Home in Michigan City
5 out of 5 average rating, 9 reviews

Pet Friendly in Beachwalk Resort - Walk to Beach,

AhmerRating, 5 stars9 months ago
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

    $100 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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