Family-friendly vacation rentals in Wilmette

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Wilmette 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
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
Chalet in Ingleside
4.84 out of 5 average rating, 387 reviews

"A" Frame Brandenburg Lake

JoelRating, 5 stars2 months ago
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.
Top guest favorite
Condo in Logan Square
4.98 out of 5 average rating, 270 reviews

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

DawnRating, 5 stars5 days ago
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!
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!
Guest favorite
Home in McHenry
4.92 out of 5 average rating, 250 reviews

River House with Deck and Hot Tub

SnehitaRating, 5 stars1 week ago
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

Guest favorite
Apartment in Logan Square
4.9 out of 5 average rating, 396 reviews

Sunny Logan Square Artists' home

TerriRating, 5 stars4 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, 337 reviews

a SIMPLE place

KaitlinRating, 5 stars1 day ago
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!
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 stars4 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

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!
Apartment in The Loop
4.63 out of 5 average rating, 60 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

ParitoshRating, 5 stars4 months ago
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!
Apartment in The Loop
4.76 out of 5 average rating, 216 reviews

Stylish Corner 2 Bedroom in the Heart of Chicago |

LauraRating, 5 stars4 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.
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.
Apartment in The Loop
4.78 out of 5 average rating, 236 reviews

Luxury Corner 2 Bedroom in the Loop | Roof Deck

SantiagoRating, 5 stars1 week ago
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

    $100 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

Destinations to explore