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Compare 276 Vacation Homes in Pleasant Prairie with updated reviews, rates, and availability.

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
8.8 out of 10, Excellent, (15)
"Came up here for s weekend with friends. Enjoyed the area. House was neat and clean. Lacking a few amenities. Kitchen items were sparse. "
The price is AED 606
AED 1,050 total
includes taxes & fees
24 Sep - 25 Sep
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Riverfront Libertyville Retreat w/ Outdoor Kitchen
8.4 out of 10, Very Good, (11)
"Location is wonderful if you are celebrating your Sailor's graduation. It's about 13 minutes away from base, however, traffic gets crazy around base so you still have to leave really early. The house itself is in a great location. The neighborhood is super quiet and we felt completely safe. The only negative thing I would have to say is that there is only 1 TV in the house that runs off WiFi and 2 of the 3 showers handle was broken, so it took us a minute to figure out you just had to turn it....
Riverfront Libertyville Retreat w/ Outdoor Kitchen
3-bedroom house WiFi in lovely Waukegan Near Gurnee
2.0 star property
5.0 out of 10, (7)
"Had to attend a 3 day funeral/celebration of life on short notice and had just returned from a tropical vacation so I didn't want to break the bank. Jake's rental was at an extremely reasonable rate which was greatly appreciated but appropriate for the site. Furniture was rearranged differently than pictured but otherwise photos were accurate. Very thankful for the convenience of parking in driveway with my mini sports car. House provided exactly what we needed which was our own private bedrooms...
3-bedroom house WiFi in lovely Waukegan Near Gurnee
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
10.0 out of 10, Exceptional, (69)
"We enjoyed our trip to Illinois. The accommodations were comfortable and just as described. "
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
Private Get A Way
10.0 out of 10, Exceptional, (10)
"8 of us traveled from across the country to see my son graduate from Navy Bootcamp, and this house was perfection! The pictures and description on Bebo don’t do it justice. It was so wonderful to have a comfortable place to hang out with my son, so much better than a hotel. We were able to sit outside at night and enjoy the gas fire pit, play football in the spacious private backyard, and eat family meals to gather again in the stocked kitchen. Any questions I had were answered within minutes by...
Private Get A Way
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, (226)
"The view is beautiful and the home is lovely and well equipped. We will certainly stay here again. It is perfect for a family reunion with lots to do. The home is clean and stocked with most everything you might need besides your clothes, food and beverages. The property manager is attentive and responsive. The location is top notch. "
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Entire 3 Bedroom Cozy Unit
8.0 out of 10, Very Good, (5)
"The rental was ok the host was really nice but if you plan on going out to downtown Chicago or any attractions the drive to get around the city will take about an hour and a half every day unless it’s nighttime… only thing u are close to at this location is six flags but other than that safe quiet area an the host lives down stairs from where u will be staying don’t know if that’s a good or bad for you an your guess but hey.. but it was cool for my first time in Chicago but I wouldn’t go back to...
The price is AED 716
AED 1,175 total
includes taxes & fees
23 Sep - 24 Sep
Entire 3 Bedroom Cozy Unit
Lake/Beach Getaway (Remodeled)
10.0 out of 10, Exceptional, (22)
"The house was perfect for us as we were visiting family in the area. House was very clean and comfortable and had everything we needed for our stay. Lake view in the morning was quite relaxing. Would stay here again. "
The price is AED 441
AED 815 total
includes taxes & fees
24 Sep - 25 Sep
Lake/Beach Getaway (Remodeled)
Lake Michigan Vacation Rental w/ Private Beach!
5.4 out of 10, (3)
"Our family of 8 stayed over the weekend at this property. The house is bigger than it looks. There is many different spaces in this home. Not everything is perfect but that is the charm of this old farm house. If you plan to use the yard make sure that it is taken care of before you stay at the property. There are several great places to go less than 20 mins away. We enjoyed the say and this a great place for a large group."
Lake Michigan Vacation Rental w/ Private Beach!
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds
8.8 out of 10, Excellent, (5)
"Good location. Fun toys for the lake, plenty of space. My only complaints, was fire pit on right side had garbage in it. I cleaned out. The black stone was not cleaned. Again we left in better condition but should be checked. We definitely needed a whisk! We were going to buy one for you but didn’t remember."
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds
The Lake House on Powers |Grassy Frontage |Lakeside Deck |Rec Room w/Pool Table & Bar |Fire Pit
10.0 out of 10, Exceptional, (3)
"Thanks so much for making this weekend one to remember! The house was fantastic and the owners were extremely cooperative with any issues we came across"
The Lake House on Powers |Grassy Frontage |Lakeside Deck |Rec Room w/Pool Table & Bar |Fire Pit
Sunset Cottage on Lake Pistakee
9.6 out of 10, Exceptional, (64)
"everything was fine but 2 fishing rods, a chair and a fishing net were stolen"
Sunset Cottage on Lake Pistakee
Modern living & Walk to downtown Libertyville ★ Great for Navy Graduations
9.4 out of 10, Exceptional, (6)
"From our initial booking until check- out all questions/requests were promptly addressed and completed. The set-up in the residence totally fit our needs. Would repeat this listing if the whole family comes back. "
Modern living & Walk to downtown Libertyville ★ Great for Navy Graduations
Fisherman's Net Beachouse - Steps from the Lake!
9.8 out of 10, Exceptional, (9)
"5/5 would recommend. Host is very nice and responsive. The beach is amazing and very close "
Fisherman's Net Beachouse - Steps from the Lake!
Beautiful Huge Lakefront Remodeled Home with Incredible Views
9.8 out of 10, Exceptional, (26)
"The home is fabulous. The view in the evening as the sun sets over the lake is one that we will remember for many years to come. My wife and I stayed on the first floor in a comfortable king size bed. My son and his wife took the master bedroom on the second floor. The enjoyed the sleep number bed. The grand daughters sleep on the bunk beds or the full-size bed. This left a free room that we did not need. The kitchen had all of the things you could hope for. They even had a smores kit for us to...
Beautiful Huge Lakefront Remodeled Home with Incredible Views
Charming 2Bd Townhome Near Beach & Base
10.0 out of 10, Exceptional, (14)
"This was perfect for our small family attending Navy graduation. Plenty of parking and comfortable. Friendly neighbors and well maintained. Thank you. "
Charming 2Bd Townhome Near Beach & Base
Lake Benedict Lakefront |Pier |Large Lawn |Fire Pit |Grill |Relaxing Family Vacation |Gas Fireplace
10.0 out of 10, Exceptional, (6)
"For the price, I have to admit, the bedrooms are outdated. But the kitchen and public areas are beautiful and the lake front property is nice. "
Lake Benedict Lakefront |Pier |Large Lawn |Fire Pit |Grill |Relaxing Family Vacation |Gas Fireplace
Lakefront Oasis w/ 2 fire pits, game room & kayaks
10.0 out of 10, Exceptional, (1)
"Our family of 11 drove to IL from RI and MS. The house was exactly as promised! We have never rented a house that was so well appointed! Everything we could have needed was in good supply and labeled for ease! We had so much room and were able to invite more family in to celebrate a full Family Christmas! We had great communication with Sarah before, during and after our stay. The location is so close to good food and we took the train to Chicago for the day! We had an amazing stay and hope to...
Lakefront Oasis w/ 2 fire pits, game room & kayaks
Spacious home in Libertyville w/ Rec Room, Wet Bar, Porch, Garage, & Fireplace
10.0 out of 10, Exceptional, (1)
"Very nice home, very comfortable to be in. Clean and nicely decorated. We were traveling with our dog and she loved the backyard, and the screened in porch to hang out in. Beds and furniture were comfortable and there was plenty of dishes, flatware, and glasses. The owner rushed to get this ready for us, and communicated with us as needed regarding progress, and what wasn't quite ready. Even though the residence is not 100% yet, it is still worth a 5 star review! Thank you VERY much!"
Spacious home in Libertyville w/ Rec Room, Wet Bar, Porch, Garage, & Fireplace
AMAZING home in Downtown Libertyville! ★ Near Naval Base ★ Stunning new Kitchen
AMAZING home in Downtown Libertyville! ★ Near Naval Base ★ Stunning new Kitchen
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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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Other property types in Pleasant Prairie

Modern Lakeside Villa
10.0 out of 10, Exceptional, (14)
"A truly amazing, beautiful, and peaceful place to vacation! Would highly recommend; great experience for the price. "
Modern Lakeside Villa
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (54)
"Nice clean home with a great view. It was wonderful to have laundry on site. And the house had everything we needed from towels to cooking supplies to water, coffee and snacks. And the water pressure and mattresses were great! We slept so well! The neighborhood was nice and quiet. I do think it could be a little cuter. But they are working on it. There is a brand new park area that’s beautiful and a great nearby place to rent any boat you might want. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
8.8 out of 10, Excellent, (15)
"Came up here for s weekend with friends. Enjoyed the area. House was neat and clean. Lacking a few amenities. Kitchen items were sparse. "
The price is AED 606
AED 1,050 total
includes taxes & fees
24 Sep - 25 Sep
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
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.