Pleasant Prairie Vacation Rentals

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Browse Select Pleasant Prairie Vacation Homes

Relax in a spacious room with high ceilings and large windows, featuring a comfortable seating area and a crib for a family-friendly stay.

"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."

Relax in this spacious living room with a large L-shaped sofa, smaller sofa, and chaise lounge.

"Had fun"

Relax on the patio with a comfortable sectional sofa and enjoy a barbecue.

"Great location close to the water cute house clean comfortable. Host was very accommodating to my allergy. Needs really enjoyed our stay highly recommend."

CA $366 total

includes taxes & fees

Aug 25 - Aug 26

Enjoy meals in this dining room with a large table and six chairs, a vase with flowers, and a comfortable rug.

"Great experience, lots of cooking materials "

CA $445 total

includes taxes & fees

Aug 10 - Aug 11

Relax in this stylish living area with a round dining table, comfortable sofa, and flat-screen TV.

"We had a group of friends stay at this property and overall really enjoyed the relaxation of the large pool, the availability of the boat dock, and the spaciousness of the house. Great time!"

Enjoy a well-lit kitchen with a stainless steel refrigerator, dishwasher, and a large window offering a neighborhood view.

"The view was spectacular!"

Relax in a serene oceanfront setting with a hammock and lush greenery.

"A small group of friends and I celebrated a birthday for a weekend here, and we loved it! The house is beautifully decorated (great for pictures) and had everything we needed. We loved the record player and backyard space. Thanks Daniel for the great stay!"

Start your day with a warm cup of coffee at the in-room coffee station.

"Close to our family and friends. "

Relax in this inviting living area with a high ceiling, comfortable sofa, and a beautiful view.

"The space of the house was great. Didnt use any of the big back yard. Had a lot of loud music the last two nights. Kept us awake . Even heard with earplugs."

Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and ample countertop space.

"Overall it was a very good experience for my family. It was just like described on the site. Marta answered my questions in timely manner."

Enjoy al fresco dining on the covered patio with a dining table, chairs, and a side table amidst a beautifully maintained lawn.

"Beautiful home, tons of room for a family. Close easy drive to Lake Geneva. We enjoyed it so much we definitely will be back."

CA $722 total

includes taxes & fees

Sep 3 - Sep 4

Kitchen area with refrigerator, sink, and cabinets, offering a convenient space for meal preparation.

"Caleb and family were so welcoming and easy to get a hold of if needed. Location was great for Kenosha and Pleasant Prairie. The apartment was perfect size and with all basic amenities needed. Thanks for a great stay! "

"Very nice and newly remodeled property. Would definitely recommend. Property owner was pleasant and attended to maintenance issues promptly. Pool table and air hockey tables were fun to play on. There is even a sauna on the property but we did not use it. Great location for being near the Naval base."

Relax in this stylish living room with a beige sofa, L-shaped sectional, and fireplace.

"Came for Navy event and had a good night's rest"

Enjoy a serene lake view from the comfort of this stylish room, featuring a wooden table, a bench with striped cushions, and a window overlooking the water.

"This clean and well appointed property was the perfect place for our stay to celebrate and spend time with family! The hosts were available and kind and there were so many thoughtful extras provided that made us feel more than at home. We will be back!!!"

Enjoy cooking in this well-equipped kitchen with a gas stove, microwave, and ample storage.

"We had a wonderful stay! The home was immaculate and had a great layout that made it easy for our family to relax and connect. The pictures do not to the home justice, it’s even nicer than it appears. Kelly was incredibly kind and responsive throughout our visit. We’d be happy to return the next time we’re in the area!"

CA $527 total

includes taxes & fees

Aug 11 - Aug 12

Enjoy expansive beachfront views and a lush, well-maintained landscape.

"Lots of room, great views, and cozy environment! Right across tge street from Lake Michigan!"

Relax by the lake in this serene outdoor seating area, featuring a fire pit and six Adirondack chairs.

"Our family gathered to visit our Carthage (Kenosha) student and view a lacrosse game. There was plenty of space for all and the outdoor area was very nice for eating and relaxing. Loved that there were multiple refrigerators, huge islands in the kitchen and a grill. We rented both units and had plenty of space for 12 people."