Pleasant Prairie Vacation Rentals

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Browse Select Pleasant Prairie Vacation Homes

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

9.0 out of 10, Wonderful, (32)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families

3-bedroom vacation home just a short walk to Lake Michigan

9.4 out of 10, Exceptional, (26)
"Great location close to the water cute house clean comfortable. Host was very accommodating to my allergy. Needs really enjoyed our stay highly recommend."
The price is CA $179
CA $366 total
includes taxes & fees
Aug 25 - Aug 26
3-bedroom vacation home just a short walk to Lake Michigan

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is CA $186
CA $445 total
includes taxes & fees
Aug 10 - Aug 11
Quaint Bungalow, near Great Lakes Naval Base

Newly Remodeled in Pistakee Bay on the Chain O' Lakes

8.6 out of 10, Excellent, (23)
"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!"
Newly Remodeled in Pistakee Bay on the Chain O' Lakes

Cute and Cozy Cottage by the Lake! Kayaks! Paddleboard! HUGE Deck w/ Great Views

9.8 out of 10, Exceptional, (34)
"The view was spectacular!"
Cute and Cozy Cottage by the Lake! Kayaks! Paddleboard! HUGE Deck w/ Great Views

Scenic Waterfront Lake Michigan Escape

10.0 out of 10, Exceptional, (12)
"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!"
Scenic Waterfront Lake Michigan Escape

Roxan Corner

8.6 out of 10, Excellent, (37)
"Close to our family and friends. "
Roxan Corner

Entire Beautiful Grove Home

9.0 out of 10, Wonderful, (11)
"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."
Entire Beautiful Grove Home

Chic Oasis/Game Room/Near Base/5 Bedroom

2.0 star property
10.0 out of 10, Exceptional, (4)
"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."
Chic Oasis/Game Room/Near Base/5 Bedroom

New Construction! Community beach access on beautiful Lake Elizabeth!

10.0 out of 10, Exceptional, (27)
"Beautiful home, tons of room for a family. Close easy drive to Lake Geneva. We enjoyed it so much we definitely will be back."
The price is CA $351
CA $722 total
includes taxes & fees
Sep 3 - Sep 4
New Construction! Community beach access on beautiful Lake Elizabeth!

Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi

2.0 star property
9.6 out of 10, Exceptional, (5)
"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! "
Cozy second floor deplex 2-bedroom in peaceful Kenosha with AC, heat and WiFi

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

10.0 out of 10, Exceptional, (1)
"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."
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

Entire 3 Bedroom Cozy Unit

9.6 out of 10, Exceptional, (18)
"Came for Navy event and had a good night's rest"
Entire 3 Bedroom Cozy Unit

Enjoy Spectacular Sunset Views ☀️ On True Lakefront

10.0 out of 10, Exceptional, (63)
"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 Spectacular Sunset Views ☀️ On True Lakefront

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (13)
"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!"
The price is CA $234
CA $527 total
includes taxes & fees
Aug 11 - Aug 12
Charming 3-bedroom house in Grayslake

Enjoy Beachfront Living With family!

9.8 out of 10, Exceptional, (80)
"Lots of room, great views, and cozy environment! Right across tge street from Lake Michigan!"
Enjoy Beachfront Living With family!

Lakefront home with firepit, 2 kitchens, & 2 W/Ds

9.2 out of 10, Wonderful, (13)
"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."
Lakefront home with firepit, 2 kitchens, & 2 W/Ds

Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table

10.0 out of 10, Exceptional, (3)
"very roomy nice deck good outside for grilling"
Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table

Chain O Lakes Lake Front Channel Lake

10.0 out of 10, Exceptional, (9)
"Enjoyed peaceful time on the lake, house was clean and comfortable. Close to all kinds of food and places we liked to go. Would recommend."
Chain O Lakes Lake Front Channel Lake
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Pleasant Prairie Hotel Reviews