
Places to stay in Pleasant Prairie
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Top-rated places to stay in Pleasant Prairie
Guests agree: these places to stay are highly rated for location, cleanliness, and more.
Vacation rentals for every style
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Popular amenities for Pleasant Prairie places to stay
Other great vacation rentals in Pleasant Prairie

Lakefront Paradise
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.

Where Family & Friends Gather to Create & Remember
We had an amazing stay! The place is beautiful & looked exactly like the pictures. We would highly recommend staying here.

Entertain on The Chain! water sports and sauna.
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.

Lake Geneva cottage with private beach access
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.

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

Living the Lakehouse Dream
We really enjoyed our stay and all the amenities your place has to offer. Thank you!

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

Huge! Sleeps 12, Perfect getaway for a large group
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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- 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
- Wicker Park
- Lincoln Park
- Lincoln Park Zoo
- Geneva National Resort & Club
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- Alpine Valley Resort
- Willis Tower
- Chicago History Museum
- Racine North Beach
- Brookfield Zoo
- Illinois Beach State Park
- Richard Bong State Recreation Area
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