House vacation rentals in Pleasant Prairie

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Popular amenities for Pleasant Prairie house rentals

House rentals with a pool

Guest favorite
Home in Highland Park
4.92 out of 5 average rating, 142 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

JeffRating, 5 stars4 months ago
We were in town for Thanksgiving visiting family with our dogs for 4 nights. Communication with host was great. The house was very clean, well furnished (we cooked the Thanksgiving meal there), recently renovated kitchen (huge kitchen island) with high end appliances, and yes there are 6 bedrooms (some small but nice). Rooms are split between three floors so everyone had room/privacy. Backyard with pool was great, lots of space for dogs, everything is fenced in but the front which was not a problem as the house is on a dead-end street with very little traffic. This is definitely a superhost home, all your condiments, lots of nice touches and snacks/gifts. We will definitely stay there again on our next visit to family in Chicago. House is locate between 41 and 94 making travel around Chicago easy.
Superhost
An expansive backyard features a well-maintained inground pool surrounded by a paved patio. Comfortable seating and a shaded area provided by a red umbrella can be seen, alongside chaise lounges. Lush green grass and fencing create a private outdoor retreat.
Home in Lake Geneva
4.64 out of 5 average rating, 11 reviews

Home in Lake Geneva Town With In Ground Pool

JackRating, 5 stars8 months ago
The property was outstanding, especially the backyard, with an oversized yard with an exceptional in-ground pool. Phenomenal sitting area w/fire pit and a very nice B-BQ. Plenty of room for 6-8 adults with everything you need, towels, kitchen utensils and two areas to watch tv. This is a can't miss rental opportunity.
Guest favorite
A spacious living area features a contemporary layout with a large, brown leather sectional sofa and a patterned area rug. Soft lighting is provided by ceiling fans and table lamps. Vintage skis and snowboards are displayed artfully on the wall beside a modern fireplace encased in stone.
Home in Twin Lakes
4.92 out of 5 average rating, 73 reviews

#EnglishPrairieBnB | 8br | 1:pm in/o | Kidquariam

RodrigoRating, 5 stars2 months ago
We had a great time at Mikes place! It was all the little things and extras. From the provided waffle mix with toppings, the golf simulator and indoor pool to the ping pong table and infinity game table. It was also very cozy and we all felt close and connected. We were a large group that gets together once a year for skiing. It was the first time we visited Wisconsin and we would definitely come back! Mike was very responsive with any issues that came up.
Guest favorite
Home in Racine
4.88 out of 5 average rating, 26 reviews

Nautical Escape •Spacious Home •Pool /Hot Tub

CarltonRating, 5 stars6 months ago
This cozy getaway was absolutely perfect for our weekend getaway!!
Superhost
Home in Wonder Lake
4.82 out of 5 average rating, 73 reviews

Great Kayaking, biking, hiking get away

RandallRating, 5 stars3 months ago
Check in was easy, and everything was as described. Julie’s place met our needs for a place to stay while visiting family. Her place is clean and well supplied. Lots of room which we didn’t use all of it. The fenced in area was nice to be able to let our dogs out.
Top guest favorite
A welcoming sitting area features original inlaid floors and large leaded glass windows, allowing natural light to fill the space. Traditional furniture includes a wooden loveseat and two accent chairs, with a round ottoman positioned centrally, enhancing the room's charm.
Home in Woodstock
4.88 out of 5 average rating, 60 reviews

Grand 1800s Victorian Gem: Updated/by Downtown

BeckyRating, 5 stars4 days ago
Deidre is an amazing host. She goes above and beyond for each guest. We always appreciate her welcoming us into her home and her attentive and responsiveness to our requests. Highly recommend!
Superhost
Home in Lake Geneva
5 out of 5 average rating, 5 reviews

Oasis on Oak | Private In-Ground Pool | Hot Tub

DeborahRating, 5 stars10 months ago
It was a beautiful, restful setting for our family to celebrate my wife’s birthday. Thank you for providing a great place for us to meet!
Top guest favorite
A wooden deck features two blue chairs accompanied by a small white table and a potted plant. The sparkling heated pool is visible, surrounded by a wooden fence and greenery, providing a serene outdoor setting.
Home in Genoa City
5 out of 5 average rating, 53 reviews

Relaxing Four Season Getaway near Lake Geneva

BascomRating, 5 stars2 months ago
We were genuinely surprised to find a place in this location so close to the relatives we were visiting. Genoa City is not exactly the hotspot on the border! The neighborhood was quiet and friendly, but no overly inquisitive citizens. Property was perfect for our requirements, with the fenced in back yard that allowed us to let our pet out whenever without having to use a leash. Nice personal welcoming touches were unexpected and truly appreciated, since we arrived late and weren't able to do any shopping before hand. Beds were comfortable and spaced throughout the second floor, with expansion in the lower basement if necessary for bigger families, especially those with older children. School immediately across the street is great for spontaneous recreation of all types if you have the equipment. Our dog has not had the opportunity to enjoy such a large open space for quite some time and it was great to wear him out for the evening prior to bedtime. Abundant TVs throughout the home!

Weekly house rentals

Superhost
A spacious living area is furnished with a large brown leather sofa accented by colorful pillows. A ceiling fan circulates air above. Nearby, a dining table with chairs sits under natural light streaming through two windows, complemented by decorative plants and textured rugs.
Home in Lake Geneva
4.94 out of 5 average rating, 145 reviews

Southwestern Vibe |Central Lake Geneva |Parking

JaeRating, 5 stars1 month ago
The home is exactly as described. It is located in a busy area but the host makes that clear in the description.. personally the gas station across the street was useful for snacks and drinks without having to drive . Shampoo / conditioner / soap and towels provided . I actually forgot my makeup wipes and those were provided too . Overall great stay .. place is super cute and home like .
Guest favorite
A paved driveway winds through a lush wooded area, bordered by greenery and tall trees. The home can be seen nestled in the distance, blending harmoniously with the natural surroundings.
Home in Muskego
4.89 out of 5 average rating, 114 reviews

Muskego Hideaway on 2 Acre Lot

MarcyRating, 5 stars1 week ago
This is our second stay at Jeff’s place and it is one of our favorites. It’s always very clean, the back yard is beautiful and perfect for dogs, and Jeff is fantastic with communication. The house has a great layout and super comfy furniture, and there is plenty of seating and a fire pit outdoors. Just an absolutely fantastic stay.
Superhost
An inviting outdoor space features a lush green lawn with well-maintained trees and shrubs lining the property. A gravel driveway leads towards a white ranch-style home and a garage, providing access to a spacious and quiet area surrounded by nature.
Home in Round Lake Beach
4.82 out of 5 average rating, 122 reviews

Modern 3 bedroom house, quiet residential street.

JoanRating, 5 stars3 weeks ago
Very clean and comfortable, nice neighborhood and not too far from our venue. Bikash was super responsive and even recommended a great place to try out Chicago deep dish pizza.
Guest favorite
A spacious living area features plush sofas arranged around a decorative coffee table. A large flat-screen TV is mounted above a stylish fireplace. Floor-to-ceiling windows allow natural light to fill the room, where a patterned area rug adds depth and texture.
Home in Waukegan
4.8 out of 5 average rating, 245 reviews

Modern home. Near naval base, Six flags and Casino

WilliamRating, 5 stars1 week ago
Great home in a great location. I would recommend this home for anyone with a large family
Top guest favorite
A quiet country home is nestled among trees and well-maintained shrubs, showcasing a wide, inviting front lawn. The façade features a mix of symmetry with multiple windows and a central entrance, complemented by a light-colored exterior that reflects a serene environment.
Home in Muskego
4.98 out of 5 average rating, 170 reviews

3 Bedroom Muskego Home

BrianRating, 5 stars1 week ago
Kathy and Tim have a wonderful place with lots of parks within a walkable distance. Tons of amenities and very helpful recommendations!
Superhost
A spacious deck features a metal gazebo enclosing a circular glass table surrounded by white chairs. A barbecue grill stands nearby, with lush green foliage and a view of Lake Elizabeth visible in the background. The sky is partly cloudy, creating a serene outdoor setting.
Home in Twin Lakes
4.84 out of 5 average rating, 150 reviews

Private Lake House, with boat option- 14 beds

TerriRating, 5 stars3 months ago
We stayed her over New Years and had a great time. The house is very open with lots of room for everyone. Beautiful views overlooking the wetlands and lake. There was plenty of beds and could easily accommodate a large group. Hot tub was in a great location out back with a beautiful view. Would love to see how beautiful it is in the summer!
Guest favorite
A rustic home with a green roof is set on a grassy area, surrounded by large trees under a clear blue sky. The house features multiple windows, providing a welcoming appearance amidst the natural landscape.
Home in Salem
4.92 out of 5 average rating, 26 reviews

Hideaway at the Ponderosa- 3bd 1Ba Country Cottage

KevinRating, 5 stars6 months ago
the host was amazing! very responsive and made check in a breeze. place was great and close to restaurants and shopping.
Guest favorite
A large, two-story home is presented with a brown wooden exterior. A spacious driveway leads to a wooden garage door, flanked by low-maintenance landscaping featuring shrubs and decorative plants. Large windows above the entrance allow natural light to illuminate the entryway.
Home in Third Lake
4.92 out of 5 average rating, 13 reviews

Home for flexible term rental

JennaRating, 5 stars3 weeks ago
We felt right at home during our stay. The house was thoughtfully arranged, well stocked, and clean. One of the cleanest stays we have had! The kitchen was well appointed. Great quality pots/pans/utensils. We cooked several meals during our stay & had everything we needed to prepare our various meals! Plenty of linens/blankets/towels out & were well displayed. There was also additional linens available if needed. All were good quality & comfortable. There was a great selection of books/board games/toys. The desk area was perfect for getting a bit of work done during our stay. The location was great & the neighborhood was so quiet. We felt safe during our entire stay. The playground across the street was so nice & there were nice sidewalks for our post-dinner strolls. The drive to the naval base was easy & not too far. Overall, we really enjoyed our stay! We will stay again if we find ourselves back in this area!

Private house rentals

Guest favorite
A modern cabin exterior showcases large glass windows framed with dark wood, allowing natural light to fill the interior. Surrounding greenery and planted flower beds enhance the serene lakeside ambiance. A stone path leads to an additional structure, contributing to the secluded environment.
Home in Powers Lake
4.78 out of 5 average rating, 64 reviews

Powers Lakehouse Loft

AnthonyRating, 5 stars6 months ago
It was exactly what we were looking for. Very quiet with beautiful views. Being able to sit in the hot tub and take in the sunset was incredible. Any questions we had were answered quickly by this very kind host.
Superhost
A cozy bedroom is showcased with rich wooden doors and a mounted television. A spacious bed is visible, covered with a light-colored quilt. Dark wood accents add character, while a small dresser complements the space. Natural light filters through a nearby glass-paneled door.
Home in Spring Grove
4.89 out of 5 average rating, 19 reviews

The April Inn - A Victorian Waterfront Retreat

PeteRating, 5 stars8 months ago
We had a short 3 night weekday getaway at Baileys place while we were having windows installed in our home. We enjoyed both the quiet location and the lake view. A Unique house style. Bailey was a pleasant and responsive host.
Superhost
An outdoor patio area is set with a large dining table and numerous comfortable chairs. The serene lake is visible in the background, framed by lush trees and a vibrant sky. A smaller table is positioned nearby, creating a tranquil space for gatherings.
Home in Bristol
4.85 out of 5 average rating, 48 reviews

Huge Lake Retreat Spa near Lake Geneva, Wilmot

CeliaRating, 5 stars1 month ago
This beautiful lake house was perfect for Our annual spring break trip with 6 teenage boys and 6 moms. Layla was very helpful and the house was beautiful. Everything was labeled which made life much easier. highly recommend and we cannot wait to return.
Top guest favorite
A spacious outdoor area is surrounded by tall trees, featuring a stone fire pit at the center with seating for eight. Colorful flower beds add a vibrant touch, while a gazebo stands nearby, enhancing the peaceful atmosphere of the large yard.
Home in Twin Lakes
5 out of 5 average rating, 32 reviews

Beautiful Twin Lakes home + lovely private setting

AmyRating, 5 stars3 months ago
This stay provided a relaxing and quiet atmosphere. Perfect space and amenities. Maria provided perfect communication and the location was safe and clean. The bedrooms are spacious and comfortable. The downstairs bedroom has an ensuite bathroom while the two bedrooms upstairs share a bathroom. The bathrooms has great amenities and are spacious as well. The kitchen was clean and had anything you could want or need to make a meal. Maria even thought of some other items like Tupperware and parchment paper. The coffee maker was serviceable. The gift basket was truly indulgent and appreciated. The big sofa was comfy and the tvs are the perfect size with any app you may want. While it was cold outside and I didn't get to enjoy the property, it was certainly still beautiful and lovely to enjoy my coffee and watch the snow in the mornings. I highly recommend this Airbnb. Thank you for letting me staying.
Superhost
A single-story home rests on a lush green lawn, surrounded by mature trees. The building features a light-colored exterior with large windows and a red door, blending into the natural landscape. Bright sunlight enhances the inviting outdoor space.
Home in Crystal Lake
4.67 out of 5 average rating, 6 reviews

4 Bedrooms 2 full baths 1 floor

VanessaRating, 5 stars3 months ago
Our family enjoyed our stay at this home! The home was comfortable, clean and stocked with amenities. Host responded quickly to one-off requests and was receptive to feedback for minor ways to improve future guest visits. We would come back in a heartbeat!
Superhost
A gray cottage is surrounded by a spacious lawn, featuring well-maintained green shrubs and a small shed nearby. Large windows provide glimpses of the inviting interior. The area is framed by trees, offering a sense of privacy and tranquility.
Home in Wonder Lake
4.9 out of 5 average rating, 10 reviews

Just Off The Lake Comfort

NatalieRating, 5 stars8 months ago
I had an incredible stay at Wanda's house! From the moment I arrived, I was greeted with warmth and hospitality. The home was exactly as described, even better in person—spotlessly clean, beautifully decorated, and equipped with everything I needed for a comfortable stay. The location was perfect for the wedding we were attending that weekend. I especially loved how cozy and convenient it was. Wanda went above and beyond to ensure I had a great experience, providing flexible check in/out times, ample snacks, and an abundance of amenities to help it feel more like home. Communication was smooth and prompt, and helped with everything we needed. I highly recommend Wanda's place to anyone looking for a relaxing and cozy stay in Wonder Lake! I can’t wait to come back.
Guest favorite
A three-story home is shown nestled among trees, with a clear view of Lake Michigan in the background. A wide driveway leads to the house, which features a balcony on the upper level. Sunlight highlights the inviting green lawn and nearby shoreline.
Home in Kenosha
5 out of 5 average rating, 25 reviews

Spectacular Lake Michigan views

donRating, 5 stars7 months ago
We had a family reunion, six adults. The house was spacious and had very nice views of the lake, especially from the deck on the first and second floors. Spent one afternoon at the beach, just half a mile away, using beach chairs available at Annette's house. We took a day trip to Milwaukee, about 50 minutes away, and visited the Mitchell conservatory and the market by the river. As for the house, it was clean and well stocked, with plenty of towels, blankets and even toiletries. The dining table seats eight, which suited us well, and we had a game night in the cozy second-floor living room. The TV had Netflix available for guests, which was a nice touch. The kitchen was clean and also well stocked. Aside from a couple of deck screen doors that were hard to slide in and out, everything worked well, including the Internet. Annette was quick to respond to questions. All in all, we had a very pleasant and comfortable stay.
Top guest favorite
A gourmet kitchen features rich wood cabinetry and a spacious central island with a granite countertop. Modern light fixtures hang above, and appliances are seamlessly integrated. The area is well-lit, showcasing stylish tile accents behind the stove, providing a welcoming space for meal preparation.
Home in Libertyville
5 out of 5 average rating, 27 reviews

Private Get A Way

ChristopherRating, 5 stars1 month ago
This place is absolutely beautiful! The pictures really don’t do it justice. It’s in a nice and peaceful area. House was very clean and the “How to” book was very helpful. Nancy was very responsive and even accommodated my group to allow early check-in. If there is one thing I would point out is the hot water temp. It’s very very hot to the point where it stings, so please be careful not to burn yourselves. On the other hand, the water never gets cold when taking a hot shower lol. I highly recommend booking!

Quick stats about house rentals in Pleasant Prairie

  • Total rentals

    10 properties

  • Nightly prices starting at

    ﺩ.ﺇ220 before taxes and fees

  • Total number of reviews

    1.3K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    10 properties include access to wifi

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