
Family-friendly holiday rentals in Oconomowoc
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Oconomowoc
Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Oconomowoc family-friendly rentals
Family-friendly home rentals with a hot tub

Hot tub getaway Extra Large capacity home
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

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.

Amazing view, Modern Space
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.

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

Country cabin, birders paradise.
If you like a peaceful country setting with beautiful walking areas (among occasional passing goats too!) and a cozy woods cabin, this is the place for you. Only minutes from downtown Stoughton, warm generous hosts, and friendly neighbors.

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
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. ♥️

This Must Be the Place- Bayview Bohemian Vibes
Easy to access beautiful home which looks just like the photos. The host was extremely responsive when I had questions - would absolutely stay again.

Riverwest Loft with city skyline view
Great dog-friendly Airbnb with free parking. Easy walk to the downtown areas and a very nice park. Only downside was the location can feel a bit dodgy later at night if you decide to walk back. Otherwise, we loved our stay and we loved Milwaukee.

Wonderful Family Home Across from Park
Matthew was very helpful and friendly… the house was amazing had everything you need to feel right at home and top of that the park was across the street.. very nice and relaxing would definitely recommend this place to anyone!

WAVES : Steps to the Harbor ~ Crash Here!
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.

Fun Lake Kosh Private Pier, Decks, Fire Pit, Grill
Wonderful home for a big family or group! Lots to do (if you’re not already busy!). The home has everything you need to rest, relax, and make killer meals. Madison is a quick 30 minute drive away as well. Highly recommend.
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!

SB 309-4 2BD2BA Apartment-Pewaukee WI
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.

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.
Quick stats about holiday rentals that are family-friendly in Oconomowoc
Total rentals
20 properties
Nightly prices starting at
₹7,791 before taxes and fees
Total number of reviews
710 reviews
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi and Pool
Local attractions
Fowler Lake Park, Crafty Cow and Kiltie Drive-In
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Madison Holiday rentals
- Lake Geneva Holiday rentals
- Wisconsin Dells Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- Green Bay Holiday rentals
- Evanston Holiday rentals
- Oshkosh Holiday rentals
- Naperville Holiday rentals
- Chicago Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Erin Hills Golf Course
- Milwaukee Public Museum
- Alpine Valley Resort
- Geneva National Resort & Club
- Lake Kegonsa State Park
- Racine North Beach
- Bradford Beach
- Grand Geneva Resort & Spa
- Milwaukee County Zoo
- Richard Bong State Recreation Area
- Wilmot Mountain Ski Resort
- Harrington Beach State Park
- Henry Vilas Zoo
- Milwaukee Country Club
- Wisconsin State Capitol
- West Bend Country Club
- Springs Water Park
- Heiliger Huegel Ski Club
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Discovery World
- Blue Mound Golf and Country Club
- America's Action Territory
- Sunburst