Family-friendly holiday rentals in Pleasant Prairie

Christine’s place was the perfect get-away for a family vacation close to home. The lake was beautiful and the place was spotless and inviting. It felt like you walked in to your own home. It’s close to places to eat and there is even a community space just a few houses down that is lively if the weather is nice. I’m hoping to come back again!

This was our second visit to Amanda’s and just like the first time, it left my boys with fun memories. We will be back next summer.

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.

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!

This was my second time staying at this lakehouse, and it was just as great as I remembered. I absolutely love the peaceful surrounding area—it's a perfect spot to relax and enjoy nature. The hosts were very responsive and helpful, answering any questions I had right away. Everything in the listing was exactly as described, and the check-in instructions were clear and easy to follow. The house was clean, comfortable, and had everything I needed. I’m already looking forward to coming back again!

Amanda is the best host I’ve ever had, she is so friendly and responsive. Her kitchen was fully equipped, she gave us the option of having firewood delivered, the place is absolutely beautiful, you walk down some stairs to get to the beach. A group of 8 moms went there for a weekend getaway and it was exactly what we needed. Thank you!

This house looks like it does in the photos. It is an easy walk to downtown in a safe area. Had a great stay overall!

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.

This place was stunning and Jenni was fabulous to work with. Literally zero complaints! Thank you so so much for everything ❤️

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!

Easy to access beautiful home which looks just like the photos. The host was extremely responsive when I had questions - would absolutely stay again.

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.

everything you need. just a few steps from one of the greatest streets in the world

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!

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.

The place had everything we needed and had two outdoor spaces to enjoy which we value in an Airbnb. A touch less private than I expected, I’d say, and lawn work noise throughout the Saturday we were there (no fault of the host!). But it was definitely clean, comfy, had a well-equipped kitchen with a blender/full-sized coffee maker/good knives, and was a great deal. Holly was also very kind to extend our reservation a day due to a family emergency.

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.

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.

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!

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.

Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!

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.

Beautiful and eclectic home. It was perfect for our group of girls visiting from all over the U.S to attend our HS Reunion. Plenty of lovely spaces to gather or a private, quiet nook to read or rest. The pool was wonderful. Beds were super comfortable. Kitchen was large enough and well stocked to prepare meals. Andy was very responsive with any issues or questions. Highly recommend!

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!