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.

Great host. Really looked after us and communicated very well.

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 had such a lovely stay! It felt like a home and was very cozy she even left fuzzy robes on the bed that added to the cozy fall vibes! The hot tub was clean and private and the unit had a beautiful view! Everything together made for the perfect relaxing get away!

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.

Eric was great and his place is lovely. Everything made us feel right at home, we really enjoyed our stay.

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!

Very peaceful stay and I started writing a play I was trying to write for a decade there. Great food and museums in easy walking distance. Also the place is extremely cozy.

Very private and peaceful, the views are very beautiful and peaceful. As a cook you always appreciate a good kitchen area

Very nice. Thank you!

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!

We felt very comfortable in this house. It was perfect for our family and close to everything we needed. Jessica was accurate in her description of the house. The upstairs neighbor was really quiet. I will definitely stay here again when in the area.

Very nice place to stay. Location was in a safe area. Parking garage was a little difficult getting in and out of with a bigger vehicle. Would definitely come back!

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.

This is a great space. The owner is very responsive and helpful. Looking forward to staying there again.

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.

Marietta was very accommodating - gave us a full refund when we originally needed to cancel and let us re book another weekend 😊

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!

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, 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.