Places to stay in Pleasant Prairie

Book unique places to stay, houses, and more on Airbnb

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Popular amenities for Pleasant Prairie places to stay

Stay near Pleasant Prairie's top sights

Pleasant Prairie Premium Outlets25 locals recommend
Bristol Renaissance Faire7 locals recommend
Franks Diner7 locals recommend
The Spot Drive-In3 locals recommend
Jelly Belly Center16 locals recommend
Festival Foods3 locals recommend

Other great vacation rentals in Pleasant Prairie

Superhost
Home in Fox Lake
4.87 out of 5 average rating, 125 reviews

Lakefront Paradise

AnkitRating, 5 stars2 weeks ago
We had an amazing stay. The area is beautiful and Nick is prompt in responding. We had no issues during our stay. If you stay the there definitely try all the local places he’s recommends for drinks/dine and won’t be disappointed. I must add that unlike some Airbnb where they ask the guests to do a whole host of things, this place had very few and reasonable rules that we were happy to comply with.
Superhost
Home in Kenosha
4.92 out of 5 average rating, 272 reviews

Where Family & Friends Gather to Create & Remember

AliciaRating, 5 stars3 weeks ago
We had an amazing stay! The place is beautiful & looked exactly like the pictures. We would highly recommend staying here.
Guest favorite
Home in Antioch
4.92 out of 5 average rating, 116 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.
Guest favorite
Home in Lake Geneva
4.91 out of 5 average rating, 116 reviews

Lake Geneva cottage with private beach access

RachelRating, 5 stars6 days ago
We had a wonderful stay at Jennifer’s place! It was a beautiful house with plenty of space for our group. Not to mention it was a stone’s throw away from the lake! We also had some personal issues that caused us to be a bit behind on checkout, and we appreciated Jennifer and Angela’s understanding.
Guest favorite
Cottage in Wonder Lake
4.93 out of 5 average rating, 137 reviews

The Cozy Lake House/ Perfect Winter Getaway!DM ?s

MelodyRating, 5 stars1 week ago
One of the best Airbnb I’ve been to. It was clean and spacious. Steve was an amazing host, he took us on a boat ride, so much fun. This place was 20/10… I would definitely recommend, we had a great time.
Guest favorite
Cabin in Trevor
4.92 out of 5 average rating, 346 reviews

Living the Lakehouse Dream

Andrea NicoleRating, 5 stars6 days ago
We really enjoyed our stay and all the amenities your place has to offer. Thank you!
Guest favorite
Home in Twin Lakes
4.86 out of 5 average rating, 65 reviews

beach access, pet friendly yard, hot tub, 5 bedrms

AaronRating, 5 stars1 month ago
Great place for our family to hang out and relax. The hot tub was great. Lots of space for everyone. The fenced in yard was great for our dog. The large gathering spaces were perfect for our kids to play games and for the adults to hang out.
Top guest favorite
Home in Lake Geneva
4.96 out of 5 average rating, 80 reviews

Huge! Sleeps 12, Perfect getaway for a large group

RachelRating, 5 stars6 days ago
This home was incredible for a weekend away with girlfriends. We loved the views of lake como m, the proximity to downtown lake Geneva, and how well stocked the house was with all the essentials and more (especially in the kitchen!). Only regret was not making our stay a full week long trip!

Quick stats about vacation rentals in Pleasant Prairie

  • Total rentals

    30 properties

  • Nightly prices starting at

    $50 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

  • Wifi availability

    30 properties include access to wifi

Frequently Asked Questions

  • How much does it cost to stay in house rentals in Pleasant Prairie?

    Experience the best of Pleasant Prairie with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there house rentals with a dedicated workspace in Pleasant Prairie?

    Yes! Work meets play with ease at over 10 house rentals in Pleasant Prairie featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • What are the most popular amenities for House Rentals in Pleasant Prairie?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do house rentals in Pleasant Prairie have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Pleasant Prairie. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Pleasant Prairie have wifi?

    Absolutely! We offer over 10 house rentals with wifi in Pleasant Prairie. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Pleasant Prairie?

    Pleasant Prairie has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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