Family-friendly vacation rentals in Pleasant Prairie

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Popular amenities for Pleasant Prairie family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A serene view of a lake at sunset, showcasing vibrant hues of orange and pink reflected on the water's surface. A covered balcony with simple outdoor furniture frames the scene, providing a peaceful spot to enjoy the picturesque surroundings.
Home in Lake Villa
4.86 out of 5 average rating, 43 reviews

Lakeside Getaway

AndreRating, 5 stars9 months ago
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!
Guest favorite
A cozy kitchen area is featured with white cabinets and a wooden countertop. Cooking appliances, including a stove and refrigerator, are visible. Two light-colored stools are placed at the counter. Shelving displays cookware and utensils. Natural wood walls complement the inviting atmosphere.
Cottage in Antioch
4.93 out of 5 average rating, 150 reviews

#4 Adorable Lake Cottage-Cypress Resort & Marine

JenniferRating, 5 stars8 months ago
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.
Guest favorite
The exterior of the home features a charming back patio area surrounded by vibrant yellow flowers. A wooden deck is furnished with a dining table and seating, while a shaded area provides additional comfort. String lights enhance the inviting outdoor space, ideal for gatherings.
Home in Milwaukee
4.95 out of 5 average rating, 231 reviews

Spacious house, yard & hot tub easy drive downtown

CharissaRating, 5 stars2 weeks ago
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 😊
A spacious deck is furnished with a dining table beneath a sun umbrella, alongside several lounge chairs. A hot tub is positioned on one side, with a view of the backyard and a garage in the distance under clear skies.
Condo in Wauwatosa
4.63 out of 5 average rating, 113 reviews

Stylistic Condo Hot Tub Tosa Village 2 blocks away

IanRating, 5 stars9 months ago
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.
Superhost
A cozy living area features warm wood paneling and two lamps providing soft lighting. A beige couch is adorned with decorative pillows, while a wooden coffee table is centered. A small dining table with chairs is visible, along with a glimpse of the kitchen area.
Cottage in Antioch
4.89 out of 5 average rating, 82 reviews

#8 Hillside Cottage at Cypress Resort & Marine

JenniferRating, 5 stars9 months ago
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.
Superhost
An archway leads to a light-filled living space with a comfortable sofa and large windows. A relaxed armchair is positioned nearby, accompanied by a table featuring a lamp and a small plant. Verdant houseplants add a refreshing touch to the room.
Home in Antioch
4.94 out of 5 average rating, 106 reviews

#1 Old Lake House at Cypress Resort & Marine

NallelyRating, 5 stars6 months ago
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!
A charming Victorian house features a welcoming front porch with rocking chairs. The entrance is flanked by lush greenery and white hydrangeas. A red brick walkway leads to the door, surrounded by well-maintained gardens and a black wrought-iron fence.
Home in Lake Geneva
4.69 out of 5 average rating, 121 reviews

Restored Victorian w Hottub , 1block to shops

LaralynneRating, 5 stars10 months ago
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.
Guest favorite
A modern kitchen features sleek white cabinetry and stainless steel appliances. A large island with bar seating is complemented by unique pendant lighting, while a subtle tile backsplash adds texture to the space. The overall design is bright and inviting.
Townhouse in Riverwest
4.92 out of 5 average rating, 241 reviews

Amazing view, Modern Space

HelenRating, 5 stars2 weeks ago
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

Guest favorite
The dining area features a wooden table with six black chairs, positioned on a decorative rug. A tall vase with dried flowers serves as a centerpiece. The kitchen area includes white cabinetry and bar stools at the counter, illuminated by pendant lighting above.
Home in Walker's Point
4.93 out of 5 average rating, 186 reviews

HGTV Renovated Home with GREAT backyard!

HaileyRating, 5 stars7 months ago
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!
Guest favorite
The image features a cozy cabin set against a backdrop of a tranquil harbor, illuminated by a warm porch light. A pathway leads to the door, bordered by a grassy area with two chairs facing the water. Trees provide additional shade and privacy.
Cabin in Kenosha
4.82 out of 5 average rating, 650 reviews

Lake Michigan Writer’s Cabin

MaryRating, 5 stars1 day ago
What a peaceful cabin! I can't recommend this stay enough, it made for a wonderful weekend getaway with our dogs!
Guest favorite
The airy living space is adorned with colorful string lights and features a cozy seating arrangement. A large window allows natural light, with a view of the balcony. A workspace with a desk, a comfortable chair, and plants enhances the inviting atmosphere.
Apartment in Riverwest
4.87 out of 5 average rating, 415 reviews

Riverwest Loft with city skyline view

DylanRating, 5 stars4 weeks ago
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.
Superhost
A bright living area features large windows letting in natural light, decorated with elegant dark curtains. Two red-accented chairs are positioned beside a small table and a lamp. A light-colored sofa faces a modern television atop a light wood stand.
Apartment in Bay View
4.92 out of 5 average rating, 117 reviews

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

ninaRating, 5 stars3 months ago
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.
Guest favorite
A bright living area is furnished with a light-colored sofa and a pink accent chair. A wooden ladder serves as decor against the wall. Large windows invite natural light, and a cabinet displays decorative items. A table sits on a patterned rug, enhancing the space.
Apartment in Racine
4.9 out of 5 average rating, 283 reviews

WAVES : Steps to the Harbor ~ Crash Here!

GarettRating, 5 stars2 weeks ago
Angela was a good communicator and the place was just what we needed for the weekend.
Superhost
An open-concept studio apartment features a spacious layout with a queen bed covered in a patterned blanket and a small futon. A cozy seating area is arranged in one corner, while a work area with a desk is visible in the background. Natural light enters through a window, complemented by warm yellow walls.
Apartment in Bay View
4.84 out of 5 average rating, 232 reviews

Cozy Basement Space In Bay View by Lake Michigan

MaKaylaRating, 5 stars3 days ago
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!
Guest favorite
An open loft space features light-colored walls and wooden beams, providing a spacious atmosphere. A large painting hangs above a cozy seating area with a fabric sofa and armchair. A simple bedside table is placed next to a spacious bed, creating a restful setting.
Loft in Walker's Point
4.84 out of 5 average rating, 426 reviews

Charming Loft - sparkling clean-walk everywhere

GayRating, 5 stars2 weeks ago
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!
Top guest favorite
Loft in Woodstock
4.96 out of 5 average rating, 196 reviews

Curated Loft Retreat in The Heart Of Woodstock

kathrynRating, 5 stars1 month ago
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

A comfortable living area features a large coffee table at its center, surrounded by a variety of seating options, including two patterned sofas and two armchairs. Bright artwork adorns the walls, and large windows provide natural light and a view of the outdoors.
Apartment in Milwaukee
4.65 out of 5 average rating, 136 reviews

Downtown One Bedroom Apartment #305

RebeccaRating, 5 stars7 months ago
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.
Guest favorite
An indoor pool area is visible, featuring clear blue water and a gently sloping entry. Large windows allow natural light to illuminate the space, revealing striped awnings overhead. Surrounding seating areas are designed with modern lounge chairs, adding to the relaxing environment.
Condo in Lake Geneva
4.84 out of 5 average rating, 70 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

TracyRating, 5 stars1 month ago
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.
Superhost
An indoor pool area is highlighted by large windows allowing natural light to fill the space. Surrounding the pool, comfortable seating arrangements are available, and mural artwork depicting serene landscapes is featured on the walls. The space maintains a cheerful atmosphere with striped ceiling decor.
Villa in Lake Geneva
4.89 out of 5 average rating, 76 reviews

2 Bedroom Villa at Lake Geneva's GRAND Resort

JaredRating, 5 stars1 month ago
This is a great space. The owner is very responsive and helpful. Looking forward to staying there again.
Condo in Lake Geneva
4.64 out of 5 average rating, 275 reviews

Flexible rental In Lake Geneva Area

LindseyRating, 5 stars2 days ago
Charming and comfortable - In the heart of Geneva close to cute shops and many restaurants! Very clean with convenient parking. Wonderful stay!
Guest favorite
A spacious driveway leads to a modern log cabin home surrounded by greenery. Flanking the driveway are several well-maintained evergreen trees. The cabin features a warm orange exterior, complementing the natural setting, with a stone accent wall visible on one side.
Cabin in Lake Geneva
4.85 out of 5 average rating, 108 reviews

Luxury Log Cabin retreat home

LizzieRating, 5 stars3 months ago
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!
Superhost
A serene outdoor pool is surrounded by a stone patio and well-maintained greenery. Lounge chairs are placed nearby, and vibrant foliage provides a peaceful backdrop. Sunlight reflects off the water's surface, creating a calming atmosphere.
Home in Lake Forest
4.9 out of 5 average rating, 63 reviews

Beautiful 137 Year Old Farm Home (3night min)

MaribethRating, 5 stars8 months ago
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!
Superhost
An indoor pool area features a circular pool with clear blue water. Ample natural light enters through large windows, enhancing the spacious atmosphere. Surrounding the pool are lounge chairs and red-striped accents along the ceiling, contributing to a lively yet relaxed environment.
Condo in Lake Geneva
4.8 out of 5 average rating, 10 reviews

2 Bedroom villa at Lake Geneva's GRAND Resort

JeremyRating, 5 stars1 month ago
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.
A multi-story resort building is shown adjacent to a swimming pool. The architecture features a central entrance with arched details, and multiple balconies overlook the well-maintained grounds. Lounge chairs are arranged around the pool area, offering a space for relaxation.
Condo in Lake Geneva
4.55 out of 5 average rating, 11 reviews

Grand Geneva in Lake Geneva

ChrisRating, 5 stars25 months ago
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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