Family-friendly vacation rentals in Waukegan

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Waukegan family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Lake Villa
4.86 out of 5 average rating, 43 reviews

Lakeside Getaway

AndreRating, 5 stars9 months ago
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!
Guest favorite
Cottage in Antioch
4.93 out of 5 average rating, 150 reviews

#4 Adorable Lake Cottage-Cypress Resort & Marine

JenniferRating, 5 stars8 months ago
This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.
Guest favorite
Home in West Town
4.85 out of 5 average rating, 313 reviews

Lux Urban 3BR/3BA Duplex + Parking!

LauraRating, 5 stars1 week ago
Our host was extremely tentative and helpful. We really enjoyed our stay at the home. It was big enough to accommodate our family plus a few other visitors, plenty of beds, plenty of living space so people didn’t have to be on top of each other. Very close to downtown and the blue line which made going to the airport and downtown much more accessible. we didn’t even have to rent a car.
Superhost
Cottage in Antioch
4.89 out of 5 average rating, 82 reviews

#8 Hillside Cottage at Cypress Resort & Marine

JenniferRating, 5 stars9 months ago
Every year we visit Cypress there are more improves and amenities. Always a great stay and so much to do. Amanda and her team run this place like a well oiled machine. We visit once in the winter and once or twice in the summer. A favorite for sure.
Superhost
Home in Antioch
4.94 out of 5 average rating, 106 reviews

#1 Old Lake House at Cypress Resort & Marine

NallelyRating, 5 stars6 months ago
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!
Apartment in Bronzeville
4.33 out of 5 average rating, 24 reviews

Spacious 2bdm unit 15min to Dwtn

Helena ORating, 5 stars3 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!
Home in Lake Geneva
4.69 out of 5 average rating, 121 reviews

Restored Victorian w Hottub , 1block to shops

LaralynneRating, 5 stars10 months ago
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.
Superhost
Home in Bristol
4.83 out of 5 average rating, 103 reviews

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski

RogerRating, 5 stars6 months ago
Great host. Really looked after us and communicated very well.

Family- and pet-friendly home rentals

Guest favorite
Apartment in Logan Square
4.9 out of 5 average rating, 395 reviews

Sunny Logan Square Artists' home

TerriRating, 5 stars3 weeks ago
Kyle's apartment was a visual feast, with fun and eclectic decor, furniture, and artwork! The listing states some quirks, which was accurate, but nothing that diminished the quality of our stay (for our family of 3). We didn't have a long enough stay to enjoy the full kitchen and dining table much, but would be a well-supplied kitchen for preparing full meals. The shower had some quirks but luckily Kyle even prepared a Youtube video to show and describe exactly how to turn on the shower. Part of the quirks of an older apartment building is radiator heating, which gives some 'clanking' and other annoying noises at times, so if you're noise-sensitive that's something to keep in mind. Kyle's local guidebook was helpful (unfortunately too long of waits at the places we had hoped to try) but found other options in the area for dinner. Our family of 3 had plenty of space for sleeping and lounging. This is a really cute space in a great location and a good close to downtown spot.
Superhost
Townhouse in Lincoln Park
4.74 out of 5 average rating, 214 reviews

Insta Worthy Prime Spot *Patio *Parking *Fireplace

LisaRating, 5 stars3 weeks ago
Alexandra’s place was a great place to stay for our group. We had two families, including 7 children, and it was great to find a place with so many queen beds to accommodate all our different sleeping needs, that also had easy access to public transit and neighborhood attractions and still had a great space where we could gather and have all of us play games/eat together comfortably after a day in the city. This was a very good experience.
Guest favorite
Guest suite in Portage Park
4.94 out of 5 average rating, 157 reviews

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

JulieRating, 5 stars1 week ago
Jamie’s place was a perfect spot to stay in Chicago. There is access to the L within a few miles (with parking structure), and there are many walkable places locally. We highly recommend Caesar Pierogis on West Irving (offers gluten free pierogis). The neighborhood is charming and safe for walking. After long days of exploring, we came back to Jamie’s place and enjoyed watching Netflix and relaxing in the living room. The kitchen is stocked with utensils, and there is a grocery store within walking distance. Jamie is a very thoughtful host, and her home is quite accommodating. We had a lovely get away. Thank you, Jamie!
Top guest favorite
Apartment in Andersonville
4.93 out of 5 average rating, 429 reviews

Andersonville Living

ChristyRating, 5 stars1 week ago
We 3 loved our stay at Joseph and William's place! The apartment was clean, bright, and filled with art. The kitchen was lovely, the beds were all comfortable and the shower was very hot. We loved the back deck, and I imagine it gets used so much in warmer weather. The location is perfect. We walked to restaurants and shops in Andersonville. It was just minutes from Loyola Univ. which is why we were in town.
Guest favorite
Townhouse in Hoffman Estates
4.91 out of 5 average rating, 336 reviews

a SIMPLE place

HannahRating, 5 stars4 days ago
My friends and I greatly enjoyed our stay over the weekend while visiting for a friend’s wedding. Steve’s home was comfortable, clean, and accommodating to our needs. We would definitely stay again!
Guest favorite
Apartment in Irving Park
4.94 out of 5 average rating, 237 reviews

Cool and Modern Chicago Apartment near Transit

AlexanderRating, 5 stars1 week ago
Definitely a great weekend! The look, and feel of the place was very comforting, and had a great flow. Design was tasteful, and anything that was needed was right where you’d expect it to be! A definite recommend!
Top guest favorite
Apartment in Logan Square
4.95 out of 5 average rating, 508 reviews

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

KathlynRating, 5 stars3 days ago
Thank you for sharing your wonderful space. It was perfect to spend time as a family while moving our daughter in Logan Square. The park nearby was so easy to manage for our dog who joined us. Paul was responsive and helpful. Got to meet his pup who was adorable. Will definitely stay here again
Guest favorite
Apartment in Evanston
4.9 out of 5 average rating, 152 reviews

Clean and Bright Stay 2BRM close NU campus

SummerRating, 5 stars5 months ago
Tracy's home is clean, comfortable, and feels like a great home to return to when you are visiting Evanston. we didn't get a chance to cook in their fabulous kitchen, but I plan to next time!!

Family-friendly home rentals with a pool

Apartment in The Loop
4.76 out of 5 average rating, 216 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

LauraRating, 5 stars3 days ago
Fantastic location, felt incredibly safe, and was exactly as described. Great space and made for the perfect spot for our family during our stay in Chicago. Would absolutely return.
Superhost
Condo in Lake Geneva
4.84 out of 5 average rating, 70 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

TracyRating, 5 stars1 month ago
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.
Superhost
Villa in Lake Geneva
4.89 out of 5 average rating, 76 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

JaredRating, 5 stars1 month ago
This is a great space. The owner is very responsive and helpful. Looking forward to staying there again.
Superhost
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars8 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!
Superhost
Condo in Lake Geneva
4.8 out of 5 average rating, 10 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

JeremyRating, 5 stars1 month ago
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.
Guest suite in Berwyn
4.67 out of 5 average rating, 43 reviews

Music Hot Spot’s Main Level

JamesRating, 5 stars2 weeks ago
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.
Condo in Lake Geneva
4.55 out of 5 average rating, 11 reviews

Grand Geneva in Lake Geneva

ChrisRating, 5 stars25 months ago
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!
Condo in Lake Geneva
4.59 out of 5 average rating, 138 reviews

NEW! Updated Lake Geneva Resort Luxury Suite

DanRating, 5 stars4 weeks ago
Kristi’s place was exactly as described. I had contacted Kristi on two occasions with questions prior to my arrival and within a matter of minutes, I had a response. I’d recommend Kristi’s place!

Quick stats about vacation rentals that are family-friendly in Waukegan

  • Total rentals

    150 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 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

Destinations to explore