
Family-friendly vacation rentals in Waukesha County
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Top-rated family-friendly rentals in Waukesha County
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Vacation rentals for every style
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Popular amenities for Waukesha County family-friendly rentals
Family-friendly home rentals with a hot tub

Spacious house, yard & hot tub easy drive downtown
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 😊

Stylistic Condo Hot Tub Tosa Village 2 blocks away
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.

Lake home on Lower Nehambin Lake
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.

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!

NEW! Updated Lake Geneva Resort Luxury Suite
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!

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.

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.

Amazing view, Modern Space
Clean, peaceful, and the view of city. was absolutely breathtaking. House was spotless and cozy. It was a great stay. Highly recommended.
Family- and pet-friendly home rentals

HGTV Renovated Home with GREAT backyard!
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!

Lake Michigan Writer’s Cabin
Incredibly pleasant, peaceful place. Right near everything we wanted to do and a lovely stay.

Riverwest Loft with city skyline view
Nathan’s place was great. Felt right at home and the art and quirkiness feels like your staying in an art installation. Which was much appreciated! Also love that it’s pet friendly as well will have to return with my dog so they can enjoy the place as much as I did. Would recommend for anyone to stay close enough to downtown to be able to go out and about and just far enough in residential area where it’s nice and quaint.

Wonderful Family Home Across from Park
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!

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

WAVES : Steps to the Harbor ~ Crash Here!
Great comfortable place with well supplied kitchen. We enjoyed our stay very much!

Cozy Basement Space In Bay View by Lake Michigan
The location was very clean, organized, and the check-in and check-out instructions were very simple and easy to follow. The accommodations matched the description accurate and was a very nice space! The environment was welcoming and the neighborhood felt safe and quiet. It was also very convenient to popular areas in the city. Carlos’ communication was thorough, detailed, and made for a calm and relaxing experience. I would stay at this same location again if I am in the area!

Charming Loft - sparkling clean-walk everywhere
My husband and I stayed here for a quick Milwaukee getaway. We loved the space and felt like we were at home. The location is perfect and walkable to everything we needed. Jori was ultra responsive and very helpful. We already talked about booking this place again!
Family-friendly home rentals with a pool

Downtown One Bedroom Apartment #305
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.

Flexible rental In Lake Geneva Area
Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!

Lakeview at CasaComo
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.

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.

Olympia VOA Oconomowoc WI Great getaway for fun
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.

2 Bedroom villa at Lake Geneva's GRAND Resort
For some reason there was an excess of furniture. We didn’t have a ton of time to spend there but it was super convenient and quiet. Kitchen was amazing. Frustrated they provided coffee but no filters for machine. Also TV - would Love the ability to stream. TV’s didn’t have that ability.

2 Bedroom Villa at Lake Geneva's GRAND Resort
This is a great space. The owner is very responsive and helpful. Looking forward to staying there again.
Destinations to explore
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- Milwaukee Public Museum
- Erin Hills Golf Course
- Six Flags Great America
- Geneva National Resort & Club
- Wilmot Mountain Ski Resort
- Grand Geneva Resort & Spa
- Alpine Valley Resort
- Lake Kegonsa State Park
- Racine North Beach
- Illinois Beach State Park
- Milwaukee Country Club
- Richard Bong State Recreation Area
- Springs Water Park
- Bradford Beach
- Heiliger Huegel Ski Club
- Moraine Hills State Park
- Harrington Beach State Park
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Milwaukee County Zoo
- America's Action Territory
- West Bend Country Club
- Discovery World
- Sunburst
- Blue Mound Golf and Country Club