Family-friendly vacation 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.

Every year we visit Cypress there are more improves and amenities. Always a great stay and so much to do. Amanda and her team run this place like a well oiled machine. We visit once in the winter and once or twice in the summer. A favorite for sure.

We absolutely loved our stay at Amanda's place. We wanted a quiet weekend out of the city and this place blew our expectations out of the water. I wish we could have stayed longer. The apartment itself and the resort overall just felt so homey and everyone we ran into were so kind. This is definitely somewhere we will have to start visiting once a year.

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!

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.

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 place is perfect for big parties. Beautiful and clean location with tons of space for 10+ people. Nice fire pit in the backyard and the host is amazing. There were a few kitchen utensils missing due to the last renters not returning things where they belong and a phone call to the host was made and he delivered brand new utensils within an hour. This place and owner really make you feel at home!

We had a great stay at the icehouse! Definitely a more historic unit but matched the descriptions and was perfect for our quick weekend getaway! Also a quick walk to everything downtown and the lake is right across the street. As long as you are not looking for something modern or fancy, this place is perfect!

The stay was very cozy and was decorated for valentines day. It was cold and snowy outside, but the cabin was warm and felt very comforting. The view was very pretty in the morning as the water was frozen over. The area was very peaceful with no outside noise.

This place was just what we needed. It was easy to find and had everything we needed. The space was welcoming and easy to visit with friends in.

We LOVED staying with Bruce & Pam and their property is amazing. They were very welcoming hosts, took great care to ensure we enjoyed our stay, and even went out of their way to accommodate our toddler with a high chair. They were wonderful on their own and their waterfront property was perfect for our young family. They have their own private beach with access to their paddle boards & firepit, have a swing set that was perfect for our toddler, and are also just a short walk to the additional community beach down the road & Wonder Lake Marina. We were able to rent a boat through the Marina and it was perfect for a fun day on the water with easy access to walk to/from the boat rental. Perfect stay, perfect hosts, and wonderful property. You won’t regret your stay for a private trip as a couple and also perfect for families with children.

Angela was very kind. Her responses were always quick. She was very helpful and accommodating and I would absolutely love to rent from her again thank you so much.

Kyle is an AMAZING host! Kyle was very helpful with recommendations in the area. The neighborhood is very nice and quiet. Kyle's home had everything we needed including our favorite snacks and beverages. The location is perfect with a variety of things to do and places to eat. Kyle made our visit to the Milwaukee area fun and enjoyable!

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!

Nice place to stay for the weekend. Grand Geneva Resort has lots to offer.

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!

Great locations and easy to get to everything we wanted to do. We had a few very minor issues that did not affect our stay and she was very responsive to the items we discussed.

Anthony’s listing was exactly as advertised. My family will use his unit again for our future visits!

Outstanding stay. The property is exactly as described and in brand new condition. We were here for an event at the Grand Geneva and the location of the villa was perfect for it. Excellent communication when booking and just before check in. Would happily visit again.

We had a great family experience at Grand Geneva Resort.