
House vacation rentals in Pleasant Prairie
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Top-rated house rentals in Pleasant Prairie
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Popular amenities for Pleasant Prairie house rentals
House rentals with a pool

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

Home in Lake Geneva Town With In Ground Pool
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.

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

Nautical Escape •Spacious Home •Pool /Hot Tub
This cozy getaway was absolutely perfect for our weekend getaway!!

Great Kayaking, biking, hiking get away
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.

Grand 1800s Victorian Gem: Updated/by Downtown
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!

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

Relaxing Four Season Getaway near Lake Geneva
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

Southwestern Vibe |Central Lake Geneva |Parking
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 .

Muskego Hideaway on 2 Acre Lot
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.

Modern 3 bedroom house, quiet residential street.
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.

Modern home. Near naval base, Six flags and Casino
Great home in a great location. I would recommend this home for anyone with a large family

3 Bedroom Muskego Home
Kathy and Tim have a wonderful place with lots of parks within a walkable distance. Tons of amenities and very helpful recommendations!

Private Lake House, with boat option- 14 beds
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!

Hideaway at the Ponderosa- 3bd 1Ba Country Cottage
the host was amazing! very responsive and made check in a breeze. place was great and close to restaurants and shopping.

Home for flexible term rental
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

Powers Lakehouse Loft
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.

The April Inn - A Victorian Waterfront Retreat
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.

Huge Lake Retreat Spa near Lake Geneva, Wilmot
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.

Beautiful Twin Lakes home + lovely private setting
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.

4 Bedrooms 2 full baths 1 floor
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!

Just Off The Lake Comfort
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.

Spectacular Lake Michigan views
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.

Private Get A Way
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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- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Milwaukee Public Museum
- Racine North Beach
- Frank Lloyd Wright Home and Studio
- Wilmot Mountain Ski Resort
- Humboldt Park
- Six Flags Great America
- Chicago History Museum
- Lincoln Park Zoo
- 875 North Michigan Avenue
- Wicker Park
- Geneva National Resort & Club
- Grand Geneva Resort & Spa
- Willis Tower
- Skokie Country Club
- Milwaukee Country Club
- Garfield Park Conservatory
- Lincoln Park
- Chicago Cultural Center
- Alpine Valley Resort
- Springs Water Park