
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.

Spacious house, yard & hot tub easy drive downtown
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 😊

Stylistic Condo Hot Tub Tosa Village 2 blocks away
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.

#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.

#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.

Amazing view, Modern Space
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!
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!

Lake Michigan Writer’s Cabin
What a peaceful cabin! I can't recommend this stay enough, it made for a wonderful weekend getaway with our dogs!

Riverwest Loft with city skyline view
Nathan’s place was great. Felt right at home and the art and quirkiness feels like your staying in an art installation. Which was much appreciated! Also love that it’s pet friendly as well will have to return with my dog so they can enjoy the place as much as I did. Would recommend for anyone to stay close enough to downtown to be able to go out and about and just far enough in residential area where it’s nice and quaint.

Allis in Dairyland-2 Bdm flat in heart of Bay View
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.

WAVES : Steps to the Harbor ~ Crash Here!
Angela was a good communicator and the place was just what we needed for the weekend.

Cozy Basement Space In Bay View by Lake Michigan
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!

Charming Loft - sparkling clean-walk everywhere
Jori was great! When someone accidentally cut the power line for WiFi she met us at the door, welcomed us in, and made us feel comfortable. We had a great location - so close to the Third Ward, easy parking, and quiet. Thank you Jori!

Curated Loft Retreat in The Heart Of Woodstock
Susan's place was so comfortable and peaceful. She is so kind and considerate, was always available to answer any questions that we had. We arrived, driving 13 hours, there were wonderful pastries and fruit awaiting in the kitchen area. The coffee was outstanding as well. Susan was so accommadating! Kate & Jim
Family-friendly home rentals with a pool

Downtown One Bedroom Apartment #305
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.

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

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

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!
Quick stats about vacation rentals that are family-friendly in Pleasant Prairie
Total rentals
10 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
10 properties include access to wifi
Popular amenities
Kitchen, Wifi, and Pool
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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Milwaukee Public Museum
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Six Flags Great America
- 875 North Michigan Avenue
- Chicago History Museum
- Lincoln Park Zoo
- Grand Geneva Resort & Spa
- Racine North Beach
- Wicker Park
- Geneva National Resort & Club
- Alpine Valley Resort
- Milwaukee Country Club
- Skokie Country Club
- Brookfield Zoo
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park
- Chicago Cultural Center
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