Family-friendly vacation rentals in Waukesha County

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Waukesha County family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
Home in Milwaukee
4.95 out of 5 average rating, 231 reviews

Spacious house, yard & hot tub easy drive downtown

CharissaRating, 5 stars1 week ago
Paul was flexible and super easy to communicate with. Check in and out are simple. Neighborhood was a quiet cul-de-sac and close to downtown. So convenient. We were a party of 9 and had plenty of room to gather and lounge. LOVED the saltwater hot tub. So relaxing at the start and end of our days 😊
Condo in Wauwatosa
4.63 out of 5 average rating, 113 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IanRating, 5 stars9 months ago
We booked for 2 weeks and enjoyed each day! Great neighborhood for walking our dog and loads of restaurants nearby to try out. The home was furnished with everything you could need. Sarah was accommodating to meet our needs and we would definitely come back here.
Guest favorite
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.
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.
Guest favorite
Townhouse in Milwaukee
4.92 out of 5 average rating, 241 reviews

Amazing view, Modern Space

HelenRating, 5 stars1 week ago
We booked the entire house—both units—for a bachelorette party, and I was able to do early check in to decorate. The girls loved staying there, and there was plenty of room for all 14 of us. It was the perfect location since we did a Lakefront Brewery tour, and the view was great! Riverwest is a great neighborhood in the heart of the city with a lot of wonderful local places, and eclectic charm!
Guest favorite
Cabin in Lake Geneva
4.85 out of 5 average rating, 108 reviews

Luxury Log Cabin retreat home

LizzieRating, 5 stars3 months ago
Debbie’s place is perfect for a relaxing getaway with friends or family. We came to Lake Geneva to bring in the New Year with two other couples and it was a Perfect getaway! We cooked a feast on Jan. 1 and were pleasantly surprised to find a fully stocked kitchen. This place is great, highly recommend!
Home in Oconomowoc
4.76 out of 5 average rating, 29 reviews

Lake home on Lower Nehambin Lake

StephRating, 5 stars9 months ago
Andrew and Lance are great hosts! We also stayed here last year and it’s always a nice and peaceful time. We kayaked and paddle boarded around the lake. My husband fished off the pier. The lake water was a nice temp. I also wfh during this time and WiFi worked well.
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!

Family- and pet-friendly home rentals

Guest favorite
Home in Milwaukee
4.93 out of 5 average rating, 186 reviews

HGTV Renovated Home with GREAT backyard!

HaileyRating, 5 stars7 months ago
Jenni and David’s place was exactly as described, it was wonderful! Jenni was so responsive, respectful and flexible! We LOVED the location of the home, it was very walkable, we always felt safe. It was close to some great restaurants and bars that we visited. I would highly recommend staying here!
Top guest favorite
Cabin in Kenosha
4.82 out of 5 average rating, 646 reviews

Lake Michigan Writer’s Cabin

AschleeRating, 5 starstoday
Came for a peaceful getaway and this cabin delivered that! Definitely keeping this place in mind for other trips
Superhost
Home in Cudahy
4.83 out of 5 average rating, 101 reviews

Wonderful Family Home Across from Park

TimerieRating, 5 stars1 month ago
We loved this house!!! It had absolutely everything we needed. Great location in a nice neighborhood across the street from a park, but just a few minutes from all the fun in Bay View and a very easy drive to downtown. The house was spotless and comfortable, and it was so nice being able to bring our dogs. We really felt at home. Thank you!
Superhost
Apartment in Milwaukee
4.92 out of 5 average rating, 117 reviews

Allis in Dairyland-2 Bdm flat in heart of Bay View

ninaRating, 5 stars3 months ago
The perfect location for my stay!! The hosts were quick to respond if I had any issues and the actual place itself was so cute.
Guest favorite
Apartment in Racine
4.9 out of 5 average rating, 283 reviews

WAVES : Steps to the Harbor ~ Crash Here!

GarettRating, 5 stars2 weeks ago
Angela was a good communicator and the place was just what we needed for the weekend.
Superhost
Apartment in Milwaukee
4.84 out of 5 average rating, 232 reviews

Cozy Basement Space In Bay View by Lake Michigan

MaKaylaRating, 5 starstoday
This was an amazing space and the hosts were wonderful! The home is beautiful and well described. It was the perfect place and I would love to stay again!
Guest favorite
Loft in Milwaukee
4.84 out of 5 average rating, 426 reviews

Charming Loft - sparkling clean-walk everywhere

GayRating, 5 stars2 weeks ago
Jori was great! When someone accidentally cut the power line for WiFi she met us at the door, welcomed us in, and made us feel comfortable. We had a great location - so close to the Third Ward, easy parking, and quiet. Thank you Jori!
Guest favorite
Condo in Milwaukee
4.82 out of 5 average rating, 109 reviews

Full Condo&Garage in Trendy Bay View Milwaukee

BriRating, 5 stars3 weeks ago
I had such a great time in Andrea’s home for the weekend! She is an excellent host, very responsive, warm and friendly. Super cozy find in Milwaukee for a little getaway. Also highly recommend the Sprocket Cafe across the street!

Family-friendly home rentals with a pool

Apartment in Milwaukee
4.65 out of 5 average rating, 136 reviews

Downtown One Bedroom Apartment #305

RebeccaRating, 5 stars6 months ago
We were in town for a wedding and Juneau Village was the perfect choice for us. The church was only 2 blocks away and the reception was about 5 so we could walk to both. Although we explored the downtown area by car the free HOP transit line is close by Juneau Village and a great option. The kitchen was very clean and equipped with all the basics. It was nice having coffee provided to brew. I liked all the windows to let in sunshine and to enjoy the view. The bed and linens were comfy. We liked the security of the building and offstreet parking spots for our vehicle. Although we didn't have time to relax by the pool it looked nice. The hotels downtown Milwaukee were expensive (and booked) so we felt this unit was a good value and convenient for us.
Condo in Lake Geneva
4.64 out of 5 average rating, 274 reviews

Flexible rental In Lake Geneva Area

AnnieRating, 5 stars1 month ago
Great place for a low cost! It had plenty of space and was clean. Note that there's not a door on the smaller "bedroom."
Condo in Lake Geneva
4.89 out of 5 average rating, 196 reviews

Lakeview at CasaComo

JamesRating, 5 stars2 months ago
nice place, was represented well in the pictures. we went for Valentines weekend and enjoyed the fireplace. It snowed our first evening there but the association cleared the drive and sidewalks quickly. I can imagine this would be a summer location with proximity and closeness to Lake Como.
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.
Condo in Oconomowoc
4.22 out of 5 average rating, 18 reviews

Olympia VOA Oconomowoc WI Great getaway for fun

ChrisRating, 5 stars42 months ago
Great condo. Clean and awesome location. Bill made the check in process simple since there is an actual office and the ladies there were friendly.
Superhost
Condo in Lake Geneva
5 out of 5 average rating, 6 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

SteveRating, 5 stars13 months ago
Outstanding stay. The property is exactly as described and in brand new condition. We were here for an event at the Grand Geneva and the location of the villa was perfect for it. Excellent communication when booking and just before check in. Would happily visit again.
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.

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