
Family-friendly vacation rentals in Wilmette
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Top-rated family-friendly rentals in Wilmette
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Wilmette 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!

Lux Urban 3BR/3BA Duplex + Parking!
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.

"A" Frame Brandenburg Lake
Stephen was a welcoming host and the cabin was exactly as described. The location is secluded and quiet, but you’re also close to groceries, restaurants and fun antique stores. Kitchen is well stocked for cooking meals, and the fireplace is cozy and perfect for relaxing. Even with snow on the ground we enjoyed strolling around the property down to the lake. A wonderful stay, we’d love to visit again.

Urban Luxury 1BR/2BA Logan Square Condo w/Garage
What an unbelievable find! This garden apartment is an 8 minute walk to my daughter’s apartment! I was looking for a place close to hers for a weekend visit. This place was perfect and it had a garage to park my car in! The interior was pristine. Beautifully decorated, the bed was comfy, big beefy towels for the shower, and you wanted for nothing! This place was fully stocked with necessities! I would recommend this place to anyone looking for an extremely nice stay in a great neighborhood with the added security of a garage to park in! Oh and there is a nice patio in the back yard if you want to sit outside on a nice day and relax! I will definitely be coming back the next time I come to visit! Thanks Bryan!

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!

River House with Deck and Hot Tub
We loved our stay! The place was really cute and clean. Eric was very responsive and we also appreciated that a couple of food items were left for us.
Family- and pet-friendly home rentals

Sunny Logan Square Artists' home
Loved our stay. Cool neighborhood with lots to do in the direct area. Great advice from Kyle about where to go. Would definitely stay again!

Insta Worthy Prime Spot *Patio *Parking *Fireplace
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.

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

Andersonville Living
These hosts are lovely as is this space. The amenities are wonderful and go beyond what they would need to provide - making travel easier! The apartment is spacious, comfy and clean. The area is full of places to go and also right on the Clark bus line, making access to the rest of the city easy peasy. Highly recommend.

a SIMPLE place
This is the 2nd time I've stayed here, and it is always exactly what I need. The space is great, the neighborhood is safe, and there's a Lou Malnatis and Portillos within a 15 min drive. Will definitely stay again!

Cool and Modern Chicago Apartment near Transit
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!

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

*Comfortable & Spacious Home Close to Downtown*
This was a very spacious and clean apartment that comfortably hosted our family of 6 for several days. Having two separate living areas was very useful and allowed our group to spread out a bit. The full-size crib in the extension area off the master bedroom was also much appreciated as we had a 2-year-old with us. The building is on a quiet street just one block from Humboldt Park and two blocks from restaurants and shops on North Avenue. There was a grocery store within 2 blocks. Dubbs was a very responsive host, and we appreciate his flexibility with checkout time. We would happily stay here again.
Family-friendly home rentals with a pool

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!

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
I had an amazing stay at this place. Felt like home.The space was clean, beautifully decorated, and thoughtfully equipped with everything I needed for a comfortable visit. The host was incredibly welcoming and responsive, making sure every detail was perfect. The location was ideal, close to local attractions yet peaceful and quiet. It truly felt like a home away from home, and I can’t wait to book again for my next trip. Highly recommended!

Stylish Corner 2 Bedroom in the Heart of Chicago |
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.

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.

Luxury Corner 2 Bedroom in the Loop | Roof Deck
The place is unbelievably well located! One block away from the Chicago Riverwalk and one block from the world famous Michigan Av. You can walk anywhere from here, including Lincoln park, the Hancock tower, Willis tower and the millennium park. Awesome place. It is noisy though! But that’s the price you pay for being right in the center of the action! The place is lovely, comfortable and very nicely furnished!
Quick stats about vacation rentals that are family-friendly in Wilmette
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ367 before taxes and fees
Total number of reviews
480 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
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- Indiana Dunes National Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Oak Street Beach
- Shedd Aquarium
- Guaranteed Rate Field
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Wilmot Mountain Ski Resort
- Six Flags Great America
- The Field Museum
- Lincoln Park Zoo
- Lincoln Park
- Wicker Park
- Museum of Science and Industry
- Chicago History Museum
- Willis Tower
- Racine North Beach
- Brookfield Zoo
- Flossmoor Golf Club
- Illinois Beach State Park