
House holiday rentals in Pleasant Prairie
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Top-rated house rentals in Pleasant Prairie
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Popular amenities for house rentals in Pleasant Prairie
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.

Woodhaven, a Luxury Lake Geneva HotTub-Pool Estate
“We had a fantastic two-day stay at Ellen’s place place! The home was exactly as described—spotlessly clean, comfortable, and well-equipped with everything I needed. The location was perfect, close to lake Geneva downtown which made exploring the area so easy. Ellen was incredibly welcoming and responsive, offering helpful tips about the area and making sure I felt right at home. The thoughtful touches, like the warm fireplace on arrival, towels in each room made my stay even more enjoyable. The hot tub was very comfortable this time of the year. I would absolutely stay here again and highly recommend it to anyone looking for a cozy and hassle-free getaway!”

Cozy cabin getaway near Lake Como and Lake Geneva
This was my first time using Airbnb. We had a group and it seemed like a better idea to try and find something we could share for the GaryCon convention. None of us were familiar with the area so I used the app and geo bracket for within 10 miles of the convention and came up with this beautiful home that had enough beds to accommodate each of us. I looked through the pics and was happy with what I saw. Sasha was responding quickly to answer my questions and we made the reservations. When we got to the place we were all happy with what we found. The hone was spacious with large beds in each room. 3 baths made it easy for us to get out quickly each morning. The kitchen was really great. The deck was really great. Seriously couldn't not have been happier and more pleased. Thank you for opening up your home to us. I understand why people live the area. I strongly recommend this home and Sasha if you're in the area.

#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.

Newly Updated Modern Lake Condo
Great location close to shops and restaurants. We enjoyed the pool/hot tub area and ended up having dinner at Crafted Italia in the same building the pool is located, it was nice and close to the rented unit.

Relaxing getaway/StepsToLake/Pool/Tennis/nearDT/WD
I absolutely love the location of this property. Steve's place is perfectly secluded for quiet mornings & peaceful evenings. I hope to return in the winter to take in the beautiful snowfall. I also appreciate the fact that it's not far from a small cozy town with a walking path along the lake. Thank you for sharing your wonderful property & I look forward to returning!

Grand 1800s Victorian Gem: Updated/by Downtown
My friends and I had a wonderful stay at Deirdre’s home! It’s a gorgeous property with lots of charm and space, and so many great amenities (theater room, claw foot bathtub, Sonos speakers, ample parking, etc.). Deirdre was also very responsive throughout the process and even helped us with a more flexible checkout time. Absolutely recommend visiting her home, we’re already wishing for another trip!

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!
Weekly house rentals

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.
We enjoyed our stay, beautiful home, very clean & organized, Bikash was attentive & responded quickly. Would stay here again! Thank you

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.

Modern home. Near naval base, Six flags and Casino
Nice home, rooms were pretty spacious & good for a family stay. Very peaceful!

3 Bedroom Muskego Home
This was our 2nd stay at this beautiful home. We love the time we get to spend at the house, watching movies (they have so many great options via Roku and DVDs & VHS too!) or playing games (many options at the house too), or reading on the back porch which is so beautiful and peaceful. Tom was very quick to respond when we had a question about the fireplace. We highly recommend!!

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
This place was perfect for my husband, our ten year old and my mother and I. Plenty of space and privacy for my mother on second floor, and for us on the first floor. Everything was well designed- there was plenty of flexible and very comfortable seating in the living room and bedrooms for hanging out, and also around the dinner table. So much natural light, and free of clutter, yet it felt homey and like someone cared about their space, not just furnished as a rental business. The neighborhood was great for playing pass in the cul de sac, or across st at park and playground, and lovely for walking. Kitchen appliances were primo, and we found everything we needed. Thank you for such an enjoyable stay!

Root River Home - Waterfront property - Sleeps 8+
Beautiful home with amazing views. Very peaceful and serene setting; you forget the house is in a small residential community. The accommodations were very comfortable with lots of room for a larger group to spread out. We would love to come back again for a longer stay to enjoy canoeing, fishing and hit the beach. Mindy was quick to respond to the few questions I had. Almost forgot, LOVED THE FIREPLACE!! Thank you!
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.

Charming, Updated and Historic
Really cool home. Easy check in and Jay was always quick to respond to any messages.

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.

White House on Wisconsin|Horticultural Hall |Sl 20
This is the perfect house for larger groups- we used it previously for my bachelorette and it was perfect for our wedding party! There’s enough space for everyone and we all very much appreciate the mix of king and queen beds!

White Pine Villa-Hot tub, Kayaks, fire pit
John's place was perfect, great location right on the river. Would love to come back again.

Quiet 3 BR house Roku, Office with printer
It was nice, quiet and peaceful place. Great place to relax and unwind. Loved my stay, the house had a very homey feel to it.
Quick stats about house rentals in Pleasant Prairie
Total rentals
10 properties
Nightly prices starting at
£45 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
- Oak Street Beach
- Milwaukee Public Museum
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- 875 North Michigan Avenue
- Six Flags Great America
- Wilmot Mountain Ski Resort
- Lincoln Park
- Wicker Park
- Lincoln Park Zoo
- Geneva National Resort & Club
- Grand Geneva Resort & Spa
- Alpine Valley Resort
- Willis Tower
- Chicago History Museum
- Racine North Beach
- Brookfield Zoo
- Illinois Beach State Park
- Richard Bong State Recreation Area
- Skokie Country Club