
Family-friendly holiday rentals in Pewaukee
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Top-rated family-friendly rentals in Pewaukee
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
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Popular amenities for Pewaukee family-friendly rentals
Family-friendly home rentals with a hot tub

Hot tub getaway Extra Large capacity home
Such a great home for our small staff retreat! Will definitely check availability for this home for future needs! Joe and Shelly are great hosts!!

6BR house, yard, hot tub - 5 min drive downtown
If i could give Paul and his home 6 stars I would. He was an excellent host. The home had everything and more than our group expected. It was close enough to down town but far enough to feel like we were away from the city.

Stylistic Condo Hot Tub Tosa Village 2 blocks away
Sarah was a wonderful host with a beautiful home! My friends and I had a great time at this spot. It was clean and comfortable. Sarah was accommodating and responsive. Also super easy to get around Tosa or easy to get downtown!

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.

Luxury Log Cabin retreat home
Debbie was very communicative before and during our stay. The property has plenty of yard room for outdoor activities and we loved that we didn’t feel stacked up against a bunch of other houses. The driveway can accommodate a group of cars and we loved the reclining couch in the basement. I’d highly recommend this property.

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft
We had a wonderful stay at Daniel’s place! The house is beautiful and the view is stunning. It was really clean and felt very welcoming. We traveled with grandparents and kids and everyone found something to enjoy. The pool table was a huge hit, as was the badminton set and the multiple outdoor seating areas. This one is highly recommended!

Lake home on Lower Nehambin Lake
We had a wonderful stay at the lake cabin. It was a great spot for our family of 5. We brought our children, ages 4, 2, and 4 months old and thought the cabin worked well for our needs. It is not particularly childproof, but we had no issues and our children loved the yard and the lake. I loved sitting on the back deck to enjoy the beautiful view in the early mornings when my infant had woken me up :) The bathroom was spacious, and the beds were comfortable. The kitchen had everything we needed and more. Everything about the stay was smooth and easy.
Family- and pet-friendly home rentals

HGTV Renovated Home with GREAT backyard!
Enjoyed our stay. Beautiful home that had everything we needed. Lovely patio area as well.

Historic Home Sleeps 16 in MKEs Best Neighborhood
Always love staying with Daniel and Anne's place! Not only are they always super responsive, but their property is beautiful and well set up for large groups. walk friendly, and lots of nearby food options. 100% would recommend, and we definitely hope to be back in the future!

Lake Michigan Writer’s Cabin
We loved the place! It was soooo peaceful! My wife and I enjoyed sitting on the deck in the morning drinking coffee and watching the boats go by. This was our first time in Kenosha and we wished we had booked a few more days to explore more! Sue was awesome and very responsive to any questions we had about the area

This Must Be the Place- Bayview Bohemian Vibes
My partner & I had a wonderful stay at “This Must Be the Place”. Was truly a relaxing getaway! Michael was very informative throughout our trip & his home was so cozy & peaceful. Everything is also very close by! So many independent owned restaurants & stores! We definitely enjoyed sitting in the patio all while cooking on the grill & watching the fire pit! 🌿

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!

Cozy Lakeside Cabin on Lake Koshkonong
My husband, two dogs and I thoroughly enjoyed our stay at the cabin! The point of my vacation was going somewhere we could take our dogs and this was the perfect spot to relax with them for a few days. Everything was clean and there was a perfect amount of space for us to relax. It was very quiet in the neighborhood and most of the time it felt like we were the only ones around. It was great to be able to walk to a very nice restaurant and bar a minute or two down from the cabin since we wanted to stay close. The only thing that bummed me out was we went at the end of May and the dock wasn’t put out - and I was hoping to spend time sitting out on the water. That could have been me not realizing the typical “season” but had assumed it’d be out so I recommend checking if that’s important to 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!
Very cute clean modern apartment. Close to the water and Main Street for walking. We had a busy weekend due to graduation events. We would book 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.

2 BD 2 BA Abbey Villa with Pool
Great spot! The condo was clean, comfortable, and quiet. It was a short walk to the beach and restaurants. Mandy’s detailed directions and instructions made checking in a breeze. Our group of four had a fantastic time.

2 Bedroom Villa at Lake Geneva's GRAND Resort
What a lovely and hospitable place! We loved our time there. The level of comfort was unmatched. We would happily return. Truly a wonderful experience!

Abbey Spring Resort Home |North Shore Hideaway
We had a fantastic time here! The property has an incredible deck that extends into the surrounding forest. We had breakfast outside every morning! If you love wildlife, you'll love this place.

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
We absolutely loved this location. We ended up not even going into Lake Geneva until we were driving out. Close to Williams Bay for the Shoreline Trail. Close to restaurants and walking distance to activities. We fished right from the dock and caught a lot of Blue Bill, Northern Pike and Bass. We encountered a lot of wild life; turtles (we watched her laying eggs, cranes, deer, a snake) Pool was fun, listened to music up at the Lodge by the fire and enjoyed the condo. It was very comfortable and welcoming. We will be back!

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.
Quick stats about holiday rentals that are family-friendly in Pewaukee
Total rentals
30 properties
Nightly prices starting at
₹3,426 before taxes and fees
Total number of reviews
750 reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi
Destinations to explore
- Downtown Chicago Holiday rentals
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- Six Flags Great America
- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Kohler-Andrae State Park
- Geneva National Resort & Club
- Illinois Beach State Park
- Bradford Beach
- Grand Geneva Resort & Spa
- Richard Bong State Recreation Area
- Racine North Beach
- Milwaukee County Zoo
- Wilmot Mountain Ski Resort
- The Bull at Pinehurst Farms Golf Course
- Milwaukee Country Club
- Harrington Beach State Park
- West Bend Country Club
- Springs Water Park
- Heiliger Huegel Ski Club
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Discovery World
- Sunburst
- Blue Mound Golf and Country Club
- America's Action Territory