Family-friendly vacation rentals in Oconomowoc

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Oconomowoc family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Home in Milwaukee
4.95 out of 5 average rating, 231 reviews

Spacious house, yard & hot tub easy drive downtown

CharissaRating, 5 stars4 weeks ago
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 😊
Condo in Wauwatosa
4.63 out of 5 average rating, 113 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IanRating, 5 stars9 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.
Home in Oconomowoc
4.76 out of 5 average rating, 29 reviews

Lake home on Lower Nehambin Lake

StephRating, 5 stars10 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.
Guest favourite
Cabin in Elkhorn
4.97 out of 5 average rating, 299 reviews

The Retreat: 5 Acre Log Cabin

MarleyRating, 5 stars1 month ago
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.
Top guest favourite
Home in Deerfield
5 out of 5 average rating, 11 reviews

5 bedroom home near Madison Area

GeraldRating, 5 stars9 months ago
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.
Home in Lake Geneva
4.69 out of 5 average rating, 121 reviews

Restored Victorian w Hottub , 1block to shops

LaralynneRating, 5 stars11 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 Riverwest
4.92 out of 5 average rating, 243 reviews

Amazing view, Modern Space

LeahRating, 5 stars2 weeks ago
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

Guest favourite
Home in Walker's Point
4.93 out of 5 average rating, 186 reviews

HGTV Renovated Home with GREAT backyard!

HaileyRating, 5 stars7 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
Home in Bay View
4.95 out of 5 average rating, 111 reviews

This Must Be the Place- Bayview Bohemian Vibes

NaomiRating, 5 stars3 months ago
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!
Superhost
Home in Cudahy
4.83 out of 5 average rating, 101 reviews

Wonderful Family Home Across from Park

TimerieRating, 5 stars1 month ago
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!
Superhost
Apartment 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 stars4 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, 284 reviews

WAVES : Steps to the Harbor ~ Crash Here!

LoriRating, 5 stars1 week ago
Great comfortable place with well supplied kitchen. We enjoyed our stay very much!
Superhost
Apartment in Bay View
4.85 out of 5 average rating, 233 reviews

Cozy Basement Space In Bay View by Lake Michigan

GeoffreyRating, 5 stars1 week ago
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!
Guest favourite
Loft in Walker's Point
4.84 out of 5 average rating, 429 reviews

Charming Loft - sparkling clean-walk everywhere

AllisonRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Milwaukee
4.82 out of 5 average rating, 110 reviews

Full Condo&Garage in Trendy Bay View Milwaukee

LeaRating, 5 stars4 weeks ago
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

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

Downtown One Bedroom Apartment #305

RebeccaRating, 5 stars7 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
Condo in Lake Geneva
4.84 out of 5 average rating, 70 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

TracyRating, 5 stars1 month 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.
Superhost
Villa in Lake Geneva
4.89 out of 5 average rating, 76 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

JaredRating, 5 stars1 month ago
This is a great space. The owner is very responsive and helpful. Looking forward to staying there again.
Condo in Lake Geneva
4.64 out of 5 average rating, 275 reviews

Flexible rental In Lake Geneva Area

LindseyRating, 5 stars2 weeks ago
Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!
Condo in Lake Geneva
4.89 out of 5 average rating, 196 reviews

Lakeview at CasaComo

JamesRating, 5 stars2 months ago
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.
Superhost
Condo in Lake Geneva
4.8 out of 5 average rating, 10 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

JeremyRating, 5 stars1 month 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.
Condo in Lake Geneva
4.55 out of 5 average rating, 11 reviews

Grand Geneva in Lake Geneva

ChrisRating, 5 stars25 months ago
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!
Condo in Lake Geneva
4.59 out of 5 average rating, 138 reviews

NEW! Updated Lake Geneva Resort Luxury Suite

DanRating, 5 stars1 month ago
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

Destinations to explore