
Family-friendly vacation rentals in Waukegan
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Waukegan
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
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Popular amenities for Waukegan family-friendly rentals
Family-friendly home rentals with a hot tub

Lakeside Getaway
Christine’s place was the perfect get-away for a family vacation close to home. The lake was beautiful and the place was spotless and inviting. It felt like you walked in to your own home. It’s close to places to eat and there is even a community space just a few houses down that is lively if the weather is nice. I’m hoping to come back again!

Hot tub getaway Extra Large capacity home
We had an amazing stay! The place is beautiful & looked exactly like the pictures. We would highly recommend staying here.

Lux Urban 3BR/3BA Duplex + Parking!
Great stay! Thanks for making it so easy. Big space for lots of family to be together and have space.

#1 Old Lake House at Cypress Resort & Marine
Amanda is the best host I’ve ever had, she is so friendly and responsive. Her kitchen was fully equipped, she gave us the option of having firewood delivered, the place is absolutely beautiful, you walk down some stairs to get to the beach. A group of 8 moms went there for a weekend getaway and it was exactly what we needed. Thank you!

Spacious 2bdm unit 15min to Dwtn
i loved this airbnb, great spot if you just want to explore chicago. max was super quick with responses and helpful with any questions i had.

Restored Victorian w Hottub , 1block to shops
The house was very centrally located and convenient to everything in Lake Geneva. It was a good size for my adult family to stay and we enjoyed the common areas for gathering. The house is old but in a way that we found quirky and charming, and overall clean and functional. There is only one shower but we didn't run out of hot water so it worked out. Parking and entry were very easy. Overall a great find and value if you are okay with an older place and want to prioritize a central location with several private bedrooms.

Bright and Beautiful Penthouse - Close to the lake
We had a great stay at Delphine's place in Uptown. The location is excellent, being on a tree-lined street, but very close to the Red Line, the Broadway bus, Andersonville, Little Asia, grocery stores and more. As we had a little kid, being right on top of the little park downstairs was also very convenient. On the flipside, it can get noisy in the summer with lots of kids/playgroups coming there, but as parents, we didn't mind. Delphine herself was very quick to respond via Whatsapp to all our queries before and during our stay. One thing to keep in mind at her place is that you are very much living in their home. If you are looking for an apartment that is only intended for guests, this is not it. While it is plenty big as a 2BR/2BA, it is full of stuff, furniture, photos, books, toys, etc. They have made a very nice office space in the main living area, but the drawback is that the living area is now very cramped. The main bedroom has 2 queen size beds in it, which is a bit weird, so we just ended up using one bed to keep our clothes on. The other bedroom with bunk beds is excellent for kids and more spacious. So overall, a great place and a great stay, and especially good if you are a couple with 1 or 2 kids. Just a bit cramped and crowded with stuff. We stayed for 2 weeks.

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft
We had a wonderful stay at Daniel’s place! The house is beautiful and the view is stunning. It was really clean and felt very welcoming. We traveled with grandparents and kids and everyone found something to enjoy. The pool table was a huge hit, as was the badminton set and the multiple outdoor seating areas. This one is highly recommended!
Family- and pet-friendly home rentals

The Biddle House (#1)
great spot, close to a brown line stop but not close enough to hear the train, clean, easy to check in, would stay there again.

Sunny Logan Square Artists' home
Our stay was absolutely perfect. Everything was nice, clean, and homey. We loved the outdoor space and the flat was well equipped for cooking and hanging in. The decor was one of a kind as well. My family of 5 had plenty of space and will stay here over and over again!

Cozy Home Living, Dogs, Kids, Free Parking, 420 OK
Jamie's place was absolutely adorable—just as pictured and described. The bedrooms were very nice, and the beds were super cozy. The kitchen was fully stocked with all the gadgets you’d need to prepare whatever you'd like, plus a few condiments, which was a nice touch. The bathroom was tidy and well-kept, with fresh, clean towels and linens provided. Jamie was more than welcoming and very accommodating to any requests. Even though she lives below the rental, she was incredibly respectful of our space—warm, friendly, and never intrusive. It truly felt like having my own little apartment. Overall, a wonderful place to stay, and I will definitely be returning.

Downtown Elegance ✨ Private Yard Parking
We were a party of 8 humans and 2 dogs, staying for the weekend. Our family had plenty of space, and the outdoor patio was a nice bonus. The kitchen was well-equipped with coffee and tea, nice new appliances, lots of dishes and utensils (we did not need a melon baller, but she had one in case we needed it!). We found it really easy to get to the L, and also convenient for walking. It was such a relief to park once and not have to drive at all. The street was nice and quiet (I mean, there were trains, because Chicago ☺️). It felt very safe, so we were comfortable taking the dogs on walks anytime. Alexandra communicated with me really well leading up to our stay, and stayed in touch throughout. We made a lot of memories, and the lovely accommodations were part of that.

Andersonville Living
We loved this cute, Craftman-style apartment. It was so homey and well arranged, nicely furnished, and beautifully decorated that we seriously wanted to move in! The owners were very thoughtful about providing what visitors will need. (They even provided a spare umbrella!) Everything was exactly as described, and communication was friendly and prompt. The only issue we had was trying to find on-street parking. We had to park several blocks away and, sadly, our car was stolen from that parking spot. Otherwise, it was a lovely neighborhood and a convenient location. Despite the parking problems, I would stay there again.

2nd floor of 1908 brick two-flat in Logan Square
Lovely flat, excellent collection of games and books. Very well stocked, super clean. Hosts were very friendly and responsive.

Stylish Chicago Apartment near Public Transit
The host was very communicative. The place was very cute and clean. It is nice to have a place to park. I would recommend this place for sure!

Spacious Garden Apartment with Sauna and Fireplace
Rick’s place offered a variety of great amenities. We felt right at home. The pool table and pinball were great additions and the neighborhood was beautiful. There was plenty of room!! Its proximity to the Northwestern University athletic fields and Linden CTA stop made everything super easy. He is very responsive and friendly. Great stay. Would recommend to anyone.
Family-friendly home rentals with a pool

Stylish Corner 2 Bedroom in the Heart of Chicago |
This host was extremely responsive and helpful. The place was clean and in a convenient location. There were some negatives, though these things were out of the host’s control so I didn’t lower my rating. I’m including these just so other people know about them before booking. The building smells strongly of marijuana, and the train is very very close and loud. The host does provide earplugs and white noise, which was helpful. While I was there, there was a leaky faucet and the AC was broken. The host offered to fix them immediately, and I appreciated their responsiveness.

2 Bedroom villa at Lake Geneva's GRAND Resort
Clean, roomy place. Short drive to stores or walk/shuttle to resort pool/restaurants. We enjoyed our stay and would definitely stay again. The only disappointment was the golf course was closed.

2 Bedroom Villa at Lake Geneva's GRAND Resort
What a lovely and hospitable place! We loved our time there. The level of comfort was unmatched. We would happily return. Truly a wonderful experience!

Luxury Log Cabin retreat home
Debbie was very communicative before and during our stay. The property has plenty of yard room for outdoor activities and we loved that we didn’t feel stacked up against a bunch of other houses. The driveway can accommodate a group of cars and we loved the reclining couch in the basement. I’d highly recommend this property.

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!

2 Bedroom villa at Lake Geneva's GRAND Resort
The rooms were very nice and seemed to have been well kept and updated. All questions were answered promptly and fully. Would recommend to anyone needing a room there.

Music Hot Spot’s Main Level
A great stay right near a Main Street. Tons of options for going out but still quiet in your space. Warning. You will smell the BBQ restaurant and you will salivating.

Grand Geneva in Lake Geneva
Place was better than I expected--looked more updated than the photos displayed. It was very roomy with a large bathroom and a full-size kitchen. With good weather, you can simply walk up the hill to the Grand Geneva. Will definitely plan to book again!
Quick stats about vacation rentals that are family-friendly in Waukegan
Total rentals
150 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
6.1K reviews
Pet-friendly rentals
70 properties allow pets
Rentals with dedicated workspaces
110 properties have a dedicated workspace
Wifi availability
150 properties include access to wifi
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- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- Six Flags Great America
- Milwaukee Public Museum
- 875 North Michigan Avenue
- The Field Museum
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Lincoln Park Zoo
- Geneva National Resort & Club
- Willis Tower
- Lincoln Park
- Alpine Valley Resort
- Wicker Park
- Illinois Beach State Park
- Grand Geneva Resort & Spa
- Brookfield Zoo
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