Holiday houses in Pleasant Prairie

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Popular amenities for Pleasant Prairie holiday rentals

Stay near Pleasant Prairie's top sights

Pleasant Prairie Premium Outlets59 locals recommend
Bristol Renaissance Faire35 locals recommend
Franks Diner24 locals recommend
The Spot Drive-In17 locals recommend
Jelly Belly Center16 locals recommend
Kenosha Kingfish Baseball Club10 locals recommend

Other great holiday rentals in Pleasant Prairie

Superhost
Home in Fox Lake
4.76 out of 5 average rating, 29 reviews

Pistakee Lake Getaway

JaniceRating, 5 stars3 months ago
Zach was very responsive and helpful with our last minute planning. The property is exactly as indicated in the photos and was very clean. Even in the winter, the lake view was exactly what we needed … very relaxing and the location is close to shopping and restaurants. Thank you, Zach, for all your help! one thing that has nothing to do with the host or the house itself … google maps has a difficult time routing you to this property … Waze is a better option. Getting to the property by turning on Gibson from the main road is a much better option and provides a more clear route. You won’t regret a stay at this property!
Guest favourite
Guest suite in Wind Lake
4.85 out of 5 average rating, 20 reviews

Secret Garden Getaway

CassidyRating, 5 stars7 months ago
Sandy was such an amazing host! She was very kind and respectful. The place was beautiful! We went for a wedding and found that the location of the Airbnb was right around the corner, super convenient and so peaceful.
Superhost
Home in Fox Lake
4.89 out of 5 average rating, 55 reviews

Stunning Lake Views, Huge Deck, Water Fun!

KymRating, 5 stars2 months ago
Absolutely Loved our stay!! There aren't enough good things to say about the view, location & beautiful house. So fun! There's a pool table, air hockey & 2 free standing video games. Spent every sunset in the Lakeview room😍 Just gorgeous beyond words! Did i mention the Bald Eagle that hangs out in the tree right outside the Lakeview bedroom? Incredible! the lake doesn't freeze over in one spot in front of the lakeview window, saw all the big birds of prey hunt. It was definitely wildlife at its finest. The owners are Very responsive & told us to be on the look out for the eagle! Fantastic time! Loved Loved Loved it & already reserved for our Wedding weekend❤️
Guest favourite
Home in North Chicago
4.95 out of 5 average rating, 19 reviews

J&J Vacay 2 story

TracyRating, 5 stars3 weeks ago
The home was beautiful & spacious. It was a perfect location to attending our Sailor’s graduation. Our sailor was able to have her own room & there was still enough room for the rest of us! The hosts were very responsive & friendly. It was a great experience! The process from booking to checking in to leaving was very easy & convenient!
Superhost
Home in West Allis
4.77 out of 5 average rating, 153 reviews

★Cozy Beach Themed Home★2 Beds★Spacious Parking★

HélèneRating, 5 stars2 months ago
Tiare’s place was per the description and comfortable. The driveway was well shoveled/cleared after the snow. Place is conveniently located for our trip purpose.
Guest favourite
Home in Antioch
4.92 out of 5 average rating, 115 reviews

Entertain on The Chain! water sports and sauna.

JoshuaRating, 5 stars2 weeks ago
Tucked along the quiet northern edge of Antioch, this house doesn’t just offer a place to stay - it gives you something to feel. Vaulted ceilings, custom barnwood beds, and raw concrete countertops set the tone: warm, solid, and built with intent. The private beach isn’t flashy - it’s better. Soft sand, still water, and no reason to rush. Grill outside, gather at the big family-style table, then sweat it all out in the sauna that feels like it was made to erase stress. The beds hit the sweet spot between firm and forgiving. Every corner of the place feels curated without being pretentious. Jewel is just up the road if you need supplies, but you’ll quickly forget the outside world exists. And Waylon? The kind of host you rarely get - quick to respond, genuinely helpful, and fully dialed in without hovering. This isn’t just a weekend rental - it’s the kind of place that makes you rethink how you spend your time off. You’ll leave better than you arrived.
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.
Guest favourite
Cabin in Trevor
4.92 out of 5 average rating, 345 reviews

Living the Lakehouse Dream

MattRating, 5 stars1 week ago
Really enjoyed staying here. The host was incredibly responsive, and the place is a perfect getaway

Quick stats about holiday rentals in Pleasant Prairie

  • Total rentals

    30 properties

  • Nightly prices starting at

    $78 AUD before taxes and fees

  • Total number of reviews

    1.7K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    30 properties include access to Wi-Fi

Destinations to explore