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

Spacious house, yard & hot tub easy drive downtown

CharissaRating, 5 stars2 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.
Guest favorite
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.
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 favorite
Townhouse in Riverwest
4.92 out of 5 average rating, 242 reviews

Amazing view, Modern Space

HelenRating, 5 stars2 weeks ago
We booked the entire house—both units—for a bachelorette party, and I was able to do early check in to decorate. The girls loved staying there, and there was plenty of room for all 14 of us. It was the perfect location since we did a Lakefront Brewery tour, and the view was great! Riverwest is a great neighborhood in the heart of the city with a lot of wonderful local places, and eclectic charm!
Guest favorite
Cabin in Lake Geneva
4.85 out of 5 average rating, 108 reviews

Luxury Log Cabin retreat home

LizzieRating, 5 stars4 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!
Superhost
Home in Bristol
4.84 out of 5 average rating, 104 reviews

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski

AimeeRating, 5 stars6 days ago
We really enjoyed our stay! My family came in from New Mexico for my daughter's wedding, and we drove in from Illinois. Unfortunately we didn't have time to enjoy the outdoor spaces, but the home was very comfortable. The garage provided a great "hang out" space. We set up bag boards and had a great time! 10 out of 10 would definitely recommend! This was my first experience staying at an Airbnb. Thankfully Will was very easy to work with and made it a positive experience.
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.

Family- and pet-friendly home rentals

Guest favorite
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!
Top guest favorite
Guesthouse in Stoughton
4.94 out of 5 average rating, 367 reviews

Country cabin, birders paradise.

SaraRating, 5 stars1 week ago
What a relaxing stay! Gwen and Ed are just a delight! Our dogs absolutely loved the whole cabin and yard. Our older dog thought the rug in the little bedroom was his personal bed :) The bed was comfortable and the bathroom might be small but it still had enough room. We saw lots of birds and enjoyed the Badfish Creek area. This place is definitely on our must return list!
Guest favorite
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 stars3 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 favorite
Apartment in Racine
4.9 out of 5 average rating, 283 reviews

WAVES : Steps to the Harbor ~ Crash Here!

GarettRating, 5 stars3 weeks ago
Angela was a good communicator and the place was just what we needed for the weekend.
Superhost
Apartment in Bay View
4.84 out of 5 average rating, 232 reviews

Cozy Basement Space In Bay View by Lake Michigan

MaKaylaRating, 5 stars1 week ago
This was an amazing space and the hosts were wonderful! The home is beautiful and well described. It was the perfect place and I would love to stay again!
Guest favorite
Condo in Milwaukee
4.82 out of 5 average rating, 110 reviews

Full Condo&Garage in Trendy Bay View Milwaukee

LeaRating, 5 stars2 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.
Top guest favorite
Condo in Fontana-on-Geneva Lake
5 out of 5 average rating, 58 reviews

2 BD 2 BA Abbey Villa with Pool

GavinRating, 5 stars8 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
4.89 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.
Superhost
Home in Fontana
4.6 out of 5 average rating, 5 reviews

Abbey Spring Resort Home |North Shore Hideaway

MichelleRating, 5 stars9 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.
Condo in Lake Geneva
4.64 out of 5 average rating, 275 reviews

Flexible rental In Lake Geneva Area

LindseyRating, 5 stars1 week 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 Oconomowoc
4.22 out of 5 average rating, 18 reviews

Olympia VOA Oconomowoc WI Great getaway for fun

ChrisRating, 5 stars42 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.

Quick stats about vacation rentals that are family-friendly in Oconomowoc

  • Total rentals

    20 properties

  • Nightly prices starting at

    $90 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