
Family-friendly vacation 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.
Vacation 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

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.

The Retreat: 5 Acre Log Cabin
Omg!!! All I can say, it's well worth it. The place is BEAUTIFUL, Yecenia put so much thought in decorating. You don't need to bring anything, but your change of clothes. Everything you need is there. Yecenia thank you so much, for taking the time and effort to make your guests feel at home. I'm definitely coming back, and please whoever book this airbnb, treat the place as if it's your home.

5 bedroom home near Madison Area
We were looking for a quiet place with enough bedrooms for several families. This place was great. It was a nice country place with a beautiful surrounding. Grandkids loved the trampoline and hot tub. The interior was clean and well taken care of. It met all our needs. There were plenty of kitchen items for us to use. The beds were comfortable and rooms spacious enough for our belongings. We kept on the go quite a bit so were only there mainly in the evening but the grandkids had enough room to unwind and play once we got back home. Yes even though we didn’t live there it felt like home . We didn’t get to enjoy the fire pit much since the outside temperature was in the high 80’s most of the time we were there, but there was plenty of wood and chairs available. If I were moving to Wisconsin this would be an ideal place to own. We absolutely enjoyed everything about this place. Katie and Scott were very responsive. Thanks for allowing us to stay.

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!

This Must Be the Place- Bayview Bohemian Vibes
What a CHARMING home! It was the perfect amount of space for our family of 5. The style of the home is boho, charming, comfortable - truly hygge (got lots of ideas to take home!). Beds were very comfortable. The living space was just enough room for us to veg and play. Hosts went out of their way to make sure we were comfortable and to provide a few toys for our kids to play with. Took us a while to figure out how to get a comfortable temperature (January) in the bedrooms , but that’s somewhat expected in older homes. Will absolutely stay there again when we come back to town!

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!

Full Condo&Garage in Trendy Bay View Milwaukee
Wonderful stay! This is a lovely condo in an excellent location! We felt very welcome and were quite comfortable. Andrea was responsive and helpful. I look forward to staying 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 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.

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.

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.

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!
Quick stats about vacation rentals that are family-friendly in Oconomowoc
Total rentals
20 properties
Nightly prices starting at
$125 CAD 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
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- Milwaukee Public Museum
- Erin Hills Golf Course
- Geneva National Resort & Club
- Wilmot Mountain Ski Resort
- Grand Geneva Resort & Spa
- Alpine Valley Resort
- Racine North Beach
- Lake Kegonsa State Park
- Richard Bong State Recreation Area
- Milwaukee Country Club
- Henry Vilas Zoo
- Heiliger Huegel Ski Club
- Springs Water Park
- Bradford Beach
- Harrington Beach State Park
- Milwaukee County Zoo
- The Mountain Top Ski & Adventure Center at Grand Geneva
- Wisconsin State Capitol
- West Bend Country Club
- Blue Mound Golf and Country Club
- America's Action Territory
- Discovery World
- Sunburst