Pleasant Prairie Vacation Rentals

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Check prices for these dates

Tonight
Jun 28 - Jun 29
Tomorrow
Jun 29 - Jun 30
Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13

Vacation Rentals in Pleasant Prairie

Modern Lakeside Villa
Outdoor spa tub

Modern Lakeside Villa

10.0 out of 10, Exceptional, (17)
"A truly amazing, beautiful, and peaceful place to vacation! Would highly recommend; great experience for the price. "
Modern Lakeside Villa
Charming 3-bedroom apartment with AC and WiFi in Waukegan.
Fridge, microwave, oven, stovetop

Charming 3-bedroom apartment with AC and WiFi in Waukegan.

9.0 out of 10, Wonderful, (6)
The price is ￥25,314
￥50,845 total
includes taxes & fees
Jun 30 - Jul 1
Charming 3-bedroom apartment with AC and WiFi in Waukegan.
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, stereo

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

9.0 out of 10, Wonderful, (30)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.8 out of 10, Excellent, (27)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Scenic Waterfront Lake Michigan Escape
Property grounds

Scenic Waterfront Lake Michigan Escape

10.0 out of 10, Exceptional, (5)
"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
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Miscellaneous

Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.

10.0 out of 10, Exceptional, (78)
"We stayed here while skiing in Wilmot. Easy drive there and back. Plenty of room upstairs and down stairs to hang out. "
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Outdoor pool, a heated pool

7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool

9.8 out of 10, Exceptional, (207)
"Great property"
The price is ￥84,579
￥145,517 total
includes taxes & fees
Jul 2 - Jul 3
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Large Group Retreat w/ secluded party room and private pool
Fridge, microwave, oven, stovetop

Large Group Retreat w/ secluded party room and private pool

8.4 out of 10, Very Good, (16)
"This property is better than advertised, it was exactly what we were hoping for. Pool area is awesome, all of the teenage boys LOVED the clubhouse, plenty of space to host. Communication with JJ was awesome. Would book again in a heartbeat and will have more stays there."
Large Group Retreat w/ secluded party room and private pool
Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table
Terrace/patio

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
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Terrace/patio

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!

9.8 out of 10, Exceptional, (86)
"One of my favorite places I've stayed at "
The price is ￥32,531
￥91,521 total
includes taxes & fees
Jun 30 - Jul 1
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Corporate Housing by MGM
Fridge, microwave, oven, stovetop

Corporate Housing by MGM

8.8 out of 10, Excellent, (9)
"We stayed here for a week for our sons Navy Graduation, 2/20/25...It was 12 mins from base, convenient, and although some reviews have that it was a little noisey, it was actually very quiet for us..quiet when we went."
The price is ￥24,504
￥43,742 total
includes taxes & fees
Jun 30 - Jul 1
Corporate Housing by MGM
Beautiful Huge Lakefront Remodeled Home with Incredible Views
Property grounds

Beautiful Huge Lakefront Remodeled Home with Incredible Views

9.8 out of 10, Exceptional, (27)
"This rental was excellent for our family vacation. We enjoyed beautiful views of the lake and sunset, meals on back deck and time spent on the lake. The owners is easy to communicate with and made us feel very welcomed. We would love to stay here again!"
Beautiful Huge Lakefront Remodeled Home with Incredible Views
Beautiful and spacious lakefront home! Close to everything!
Terrace/patio

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (46)
"This property is beautiful!!! Very spacious and plenty of room for all of us. The bedrooms are all great sizes with room for pack n plays. Beautiful view of the lake! The kitchen was very stocked with plenty of dishes and cookware and your basic cooking needs. "
Beautiful and spacious lakefront home! Close to everything!
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Terrace/patio

🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲

9.4 out of 10, Exceptional, (103)
"The lakehouse super nice, owner communicated well, overall Good experience. A bit of feedback because the coffee machine was missing the pot so we had to go out to buy some. It was also a bit dusty. Check out was 11am and I received a text at 8:30am that cleaning crew was on the way so it felt rushed. Also, I would rather pay a cleaning fee (I understand garbage being taken out and cleaning up tables). Overall nice experience and owner did let us know jacuzzi was a bit stained from leaves so we...
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Chain O Lakes Lake Front Channel Lake
Miscellaneous

Chain O Lakes Lake Front Channel Lake

10.0 out of 10, Exceptional, (7)
"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
Enjoy Lakefront living with family!
On the beach, beach towels

Enjoy Lakefront living with family!

9.8 out of 10, Exceptional, (69)
"Great location. Comfortable housing."
Enjoy Lakefront living with family!
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
A heated pool

Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19

9.4 out of 10, Exceptional, (6)
"The boat was super clean, the bed was comfy, the host was communicative, and all the instructions were clear. We enjoyed the onsite hot tub and restaurant, and there’s plenty to do within walking distance as well."
The price is ￥19,518
￥32,031 total
includes taxes & fees
Jun 30 - Jul 1
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Entire Beautiful Grove Home
Smart TV, fireplace

Entire Beautiful Grove Home

9.0 out of 10, Wonderful, (10)
"It was an absolute delight. It is a beautiful home. Wonderful for Navy bootcamp famlies at graduation, 3 minutes from base!"
Entire Beautiful Grove Home
Wisconsin Treehouse Getaway!
Exterior

Wisconsin Treehouse Getaway!

9.8 out of 10, Exceptional, (21)
"Had a great time very relaxing with the creek there"
The price is ￥18,877
￥36,533 total
includes taxes & fees
Jul 1 - Jul 2
Wisconsin Treehouse Getaway!
Entire 3 Bedroom Cozy Unit
Smart TV, books

Entire 3 Bedroom Cozy Unit

9.4 out of 10, Exceptional, (15)
"First of all the place looked just like the pictures which we so appreciate! The property was very clean and had everything you would need! Location was very nice and felt like a very safe neighborhood. I would definitely stay there again as it checked all the boxes. Also, I really appreciated how quickly Karla got back to me every time I had a question. Thanks for a great stay....cheers!"
Entire 3 Bedroom Cozy Unit
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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Frequently asked questions

Can I find vacation rentals in Pleasant Prairie?

Yes, we give you a choice of vacation rentals in Pleasant Prairie close to Jelly Belly Center, or you can select a more remote option if you want a relaxing stay. The shops and restaurants are several reasons why visitors like Pleasant Prairie. Make sure you have time to check out the lake views and temples during your trip.

What's the top vacation rental that Pleasant Prairie has to offer?

Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families : This vacation home rental outside of Pleasant Prairie has air-conditioning and WiFi to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals are there in Pleasant Prairie?

With 5 Expedia vacation rentals, you're sure to find just the right place for your Pleasant Prairie stay.

What can I see and do in Pleasant Prairie?

Lake Michigan and North Point Marina Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Jelly Belly Center. In the larger area, you’ll find popular places like Six Flags Great America and Naval Base Great Lakes.

What are vacation rentals like in Pleasant Prairie?

Vacation rentals are private properties you can stay in for a few days or a quick weekend in Pleasant Prairie. Vacation rentals offer amenities like laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from shared hotel elevators and busy front desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive choice for family trips or small group gatherings.