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 favourite
Home in Milwaukee
4.95 out of 5 average rating, 230 reviews

Spacious house, yard & hot tub easy drive downtown

NoahRating, 5 stars5 months ago
Great place! Fairly private and very comfortable stay with 7 folks.
Condo in Wauwatosa
4.63 out of 5 average rating, 113 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IanRating, 5 stars8 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 favourite
Condo in Lake Geneva
4.84 out of 5 average rating, 69 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

HerbertRating, 5 stars2 months ago
Anthony’s listing was exactly as advertised. My family will use his unit again for our future visits!
Home in Lake Geneva
4.69 out of 5 average rating, 120 reviews

Restored Victorian w Hottub , 1block to shops

LaralynneRating, 5 stars9 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 favourite
Townhouse in Milwaukee
4.92 out of 5 average rating, 239 reviews

Amazing view, Modern Space

KrisRating, 5 stars3 weeks ago
My stay at The Lavender Inn's upstairs townhouse was absolutely wonderful. The space was impeccably clean and thoughtfully designed with modern amenities. The views from the balconies, particularly while relaxing in the jacuzzi, were simply breathtaking. I was impressed by the thoroughness of the stocking – everything I needed in the kitchen and bathrooms was readily available. The gas cooktop and fireplace was a lovely touch. I wholeheartedly recommend this property for a luxurious and comfortable getaway.
Guest favourite
Cabin in Lake Geneva
4.85 out of 5 average rating, 108 reviews

Luxury Log Cabin retreat home

LizzieRating, 5 stars2 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 stars8 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.

Family- and pet-friendly home rentals

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

HGTV Renovated Home with GREAT backyard!

HaileyRating, 5 stars6 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!
Guest favourite
Cabin in Kenosha
4.82 out of 5 average rating, 638 reviews

Lake Michigan Writer’s Cabin

AditRating, 5 stars1 day ago
We had a wonderful time in Nikos and Sue's cabin! Located next to the city marina, it is a peaceful and cosy cabin with really nice views (including Lake Michigan). The host was friendly and gave timely instructions to make things smooth, in addition to the lovely decor they had in the cabin. Also, the city beach is a short walk. Would love to visit again!
Guest favourite
Apartment in Milwaukee
4.86 out of 5 average rating, 411 reviews

Riverwest Loft with city skyline view

BrianaRating, 5 stars1 month ago
This is my 2nd time staying at this location- this time with my husband & our two small dogs. Cozy, funky & great area! Would definitely stay again!
Superhost
Home in Cudahy
4.83 out of 5 average rating, 99 reviews

Wonderful Family Home Across from Park

PaulaRating, 5 stars2 months ago
This place was just what we needed. It was easy to find and had everything we needed. The space was welcoming and easy to visit with friends in.
Guest favourite
Home in Mequon
4.92 out of 5 average rating, 60 reviews

Mequon Wedding Retreat

LianeRating, 5 stars5 months ago
David met us for check in and walked through everything! Throughout the reservation process and when we left he was very responsive. It was a beautiful home!!
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 stars2 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
Apartment in Racine
4.9 out of 5 average rating, 279 reviews

WAVES : Steps to the Harbor ~ Crash Here!

EricRating, 5 stars2 weeks ago
Satisfied return customer, looking to book again in the future.
Guest favourite
Home in West Allis
4.84 out of 5 average rating, 55 reviews

3BR Duplex With Garage Just Outside of the City

JillRating, 5 stars19 months ago
We felt very comfortable in this house. It was perfect for our family and close to everything we needed. Jessica was accurate in her description of the house. The upstairs neighbor was really quiet. I will definitely stay here again when in the area.

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 stars5 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, 272 reviews

Flexible rental In Lake Geneva Area

SarahRating, 5 stars1 month ago
We really enjoyed our stay here. The place was very nice and cozy. The bed in the master was very comfortable. Very clean and wasn’t too hard to find. The location is great right next to the Lodge and not too far from downtown. We would definitely stay there again! The only negative I have is I did try to reach out to the host before our stay to ask a question and never received a response back. But all in all we loved this place!
Superhost
Condo in Lake Geneva
4.78 out of 5 average rating, 9 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

NateRating, 5 stars8 months ago
Nice place to stay for the weekend. Grand Geneva Resort has lots to offer.
Condo in Oconomowoc
4.22 out of 5 average rating, 18 reviews

Olympia VOA Oconomowoc WI Great getaway for fun

ChrisRating, 5 stars41 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, 5 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

SteveRating, 5 stars11 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, 74 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

PrzemyslawRating, 5 stars2 months ago
We had a great family experience at Grand Geneva Resort.

Destinations to explore