Family-friendly holiday rentals in Waukesha

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Waukesha family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Home in Kenosha
4.92 out of 5 average rating, 276 reviews

Hot tub getaway Extra Large capacity home

ColeRating, 5 stars6 days ago
This was a very nice house and it accommodated 16 people with no problem at all. The host is very responsive and it was very clean and felt like home
Guest favourite
Home in Milwaukee
4.95 out of 5 average rating, 234 reviews

6BR house, yard, hot tub - 5 min drive downtown

FrankRating, 5 stars2 weeks ago
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.
Apartment in Wauwatosa
4.63 out of 5 average rating, 114 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IrelandRating, 5 stars10 months ago
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!
Guest favourite
Apartment in Lake Geneva
4.84 out of 5 average rating, 70 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

TracyRating, 5 stars2 months 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
4.67 out of 5 average rating, 123 reviews

Restored Victorian w Hottub , 1block to shops

GraceRating, 5 stars6 days ago
This house looks like it does in the photos. It is an easy walk to downtown in a safe area. Had a great stay overall!
Guest favourite
Townhouse in Riverwest
4.92 out of 5 average rating, 245 reviews

Amazing view, Modern Space

TammyRating, 5 stars1 month ago
This place was súper clean and beautiful. We were very comfortable and never heard the neighbors downstairs. The only thing that happened was the that the thermostat stopped working and they weren’t able to come and fix it. Then the bathroom switch kept tripping and we had to find the fuse box and various times the light didn’t work. But it was such a nice place and I would totally stay there again. We had a very comfortable experience.
Top guest favourite
Home in Kenosha
4.94 out of 5 average rating, 152 reviews

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft

DianeRating, 5 stars3 weeks ago
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!
Home in Oconomowoc
4.77 out of 5 average rating, 30 reviews

Lake home on Lower Nehambin Lake

KappieRating, 5 stars2 weeks ago
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

Guest favourite
Home in Walker's Point
4.93 out of 5 average rating, 188 reviews

HGTV Renovated Home with GREAT backyard!

JoshRating, 5 stars2 weeks ago
This place was stunning and Jenni was fabulous to work with. Literally zero complaints! Thank you so so much for everything ❤️
Superhost
Home in Walker's Point
4.89 out of 5 average rating, 231 reviews

Historic Home Sleeps 16 in MKEs Best Neighborhood

LynneRating, 5 stars8 months ago
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!
Guest favourite
Cabin in Kenosha
4.83 out of 5 average rating, 661 reviews

Lake Michigan Writer’s Cabin

MaryRating, 5 stars1 week ago
The cabin is very cute great location. right by Kenosha harbor. They have great amenities, shampoo, snacks. we got to enjoy our favorite restaurant Carl's pizza. ♥️
Guest favourite
Home in Bay View
4.95 out of 5 average rating, 116 reviews

This Must Be the Place- Bayview Bohemian Vibes

KristenRating, 5 stars1 week ago
Easy to access beautiful home which looks just like the photos. The host was extremely responsive when I had questions - would absolutely stay again.
Guest favourite
Flat in Racine
4.91 out of 5 average rating, 291 reviews

WAVES : Steps to the Harbor ~ Crash Here!

MaryRating, 5 stars6 days ago
We really enjoyed our stay. Very convenient and could walk to the water. The little deck in back was a nice spot to have coffee.
Superhost
Flat in Bay View
4.92 out of 5 average rating, 117 reviews

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

ninaRating, 5 stars5 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 favourite
Home in Racine
4.94 out of 5 average rating, 161 reviews

Root River Home - Waterfront property - Sleeps 8+

LyRating, 5 stars6 days ago
Great weekend stay! The house was spacious, clean, and had everything we needed for a home away from home. Loved the outdoor space, plus it was dog-friendly with kayaks, games, and a ping pong table. Peaceful location and great communication—would definitely stay again!
Superhost
Chalet in Williams Bay
4.88 out of 5 average rating, 253 reviews

The Bay Chalet

KaitlinRating, 5 stars1 week ago
The place had everything we needed and had two outdoor spaces to enjoy which we value in an Airbnb. A touch less private than I expected, I’d say, and lawn work noise throughout the Saturday we were there (no fault of the host!). But it was definitely clean, comfy, had a well-equipped kitchen with a blender/full-sized coffee maker/good knives, and was a great deal. Holly was also very kind to extend our reservation a day due to a family emergency.

Family-friendly home rentals with a pool

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

Downtown One Bedroom Apartment #305

RebeccaRating, 5 stars8 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.
Guest favourite
Apartment in Fontana-on-Geneva Lake
5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

GavinRating, 5 stars10 months ago
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.
Superhost
Villa in Lake Geneva
4.9 out of 5 average rating, 77 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

LoriRating, 5 stars3 weeks ago
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!
Superhost
Home in Fontana
4.6 out of 5 average rating, 5 reviews

Abbey Spring Resort Home |North Shore Hideaway

MichelleRating, 5 stars11 months ago
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.
Apartment in Lake Geneva
4.64 out of 5 average rating, 277 reviews

Flexible rental In Lake Geneva Area

LindseyRating, 5 stars1 month ago
Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!
Flat in Pewaukee

SB 309-4 2BD2BA Apartment-Pewaukee WI

RyRating, 5 stars40 months ago
Spent a good week at this apartment with my sister, and everything was clean, well ordered, and comfortable. Everything you need is provided. Check in and check out was a breeze, and communication with Jerry was smooth and prompt. Highly recommended for a stay in the Pewaukee/Waukesha area.
Apartment in Lake Geneva
4.89 out of 5 average rating, 198 reviews

Lakeview at CasaComo

LisaRating, 5 stars1 week ago
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!
Superhost
Apartment in Lake Geneva
4.8 out of 5 average rating, 10 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

JeremyRating, 5 stars3 months 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.

Quick stats about holiday rentals that are family-friendly in Waukesha

  • Total rentals

    20 properties

  • Total number of reviews

    460 reviews

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi and Pool

Destinations to explore