
Family-friendly vacation rentals in Pleasant Prairie
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Top-rated family-friendly rentals in Pleasant Prairie
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Pleasant Prairie family-friendly rentals
Family-friendly home rentals with a hot tub

Lakeside Getaway
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!

#4 Adorable Lake Cottage-Cypress Resort & Marine
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.

#8 Hillside Cottage at Cypress Resort & Marine
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.

#10 Lakeview Apartment at Cypress Resort & Marine
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!

#1 Old Lake House at Cypress Resort & Marine
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!

Restored Victorian w Hottub , 1block to shops
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.
Family- and pet-friendly home rentals

HGTV Renovated Home with GREAT backyard!
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!

Clean Country living at its best!
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!

Lake Geneva- Historic ice house
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!

Lake Michigan Writer’s Cabin
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.

Coach House! Ideal for Families & Remote Workers
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.

WAVES : Steps to the Harbor ~ Crash Here!
Very private and peaceful, the views are very beautiful and peaceful. As a cook you always appreciate a good kitchen area

Cozy Basement Space In Bay View by Lake Michigan
Very nice. Thank you!

Top notch Bayview Beauty (single family)
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!
Family-friendly home rentals with a pool

Luxury Log Cabin retreat home
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 137 Year Old Farm Home (3night min)
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!

2 Bedroom villa at Lake Geneva's GRAND Resort
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.

Grand Geneva in Lake Geneva
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!

2 Bedroom villa at Lake Geneva's GRAND Resort
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.

2 Bedroom villa at Lake Geneva's GRAND Resort
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.

2 Bedroom Villa at Lake Geneva's GRAND Resort
This is a great space. The owner is very responsive and helpful. Looking forward to staying there again.
Quick stats about vacation rentals that are family-friendly in Pleasant Prairie
Total rentals
20 properties
Nightly prices starting at
$70 before taxes and fees
Total number of reviews
1K reviews
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Millennium Park
- Wrigley Field
- United Center
- Milwaukee Public Museum
- Navy Pier
- Wilmot Mountain Ski Resort
- Racine North Beach
- Frank Lloyd Wright Home and Studio
- Grand Geneva Resort & Spa
- Lincoln Park Zoo
- Six Flags Great America
- Geneva National Resort & Club
- Brookfield Zoo
- Humboldt Park
- Skokie Country Club
- Milwaukee Country Club
- Springs Water Park
- Illinois Beach State Park
- 875 North Michigan Avenue
- Skydeck Chicago
- Chicago Cultural Center
- The 606
- Lincoln Park
- Chicago History Museum
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