Pleasant Prairie Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Pleasant Prairie

Modern Lakeside Villa
Property grounds
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
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, (227)
"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
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
9.4 out of 10, Exceptional, (15)
"The place was clean and had everything as advertised. IT was real close to Navy Graduation which was our primary goal. The back porch was nice too."
The price is HK$1,282
HK$2,215 total
includes taxes & fees
15 Oct - 16 Oct
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Heated Pool, Hot Tub, Fishing Pond, Game Room, Read Description
Outdoor pool, a heated pool
Heated Pool, Hot Tub, Fishing Pond, Game Room, Read Description
9.8 out of 10, Exceptional, (191)
"We had a great time enjoying the pool and fishing pond with our grand daughter. Host was easy and available with information. We appreciated so many of the many details that made for a great stay (2 kinds of coffee makers, ridge in pool, comfortable poolside chairs) it was ideal for keeping lots of people entertained, with spots for late night fires playing games chairs) clearly had machairs. Itthere"
The price is HK$2,915
HK$6,186 total
includes taxes & fees
15 Oct - 16 Oct
Heated Pool, Hot Tub, Fishing Pond, Game Room, Read Description
Roxan Corner
Terrace/patio
Roxan Corner
8.6 out of 10, Excellent, (25)
"The pics did not mislead. It was nice and roomy for my guests and I. It could’ve been cleaner but overall enjoyed the house"
Roxan Corner
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
Property grounds
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
9.4 out of 10, Exceptional, (59)
"Excellent"
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
Quaint Bungalow, near Great Lakes Naval Base
TV, books
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (54)
"With my daughter moving back to Illinois, we needed to help her get acclimated back to school. As former residence of Illinois, we still have plenty of family and friends that reside there and needed a good central location to stay. Hotels are overrated and just inconvenient. This little charming gem in the northern Of Chicago and was able to call at home for four nights. Super cute bungalow in a fabulous walkable distance to restaurants and shops, centrally located to amazing shopping. The...
The price is HK$1,049
HK$2,433 total
includes taxes & fees
11 Oct - 12 Oct
Quaint Bungalow, near Great Lakes Naval Base
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Property grounds
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (55)
"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.
Entire 3 Bedroom Cozy Unit
Smart TV, books
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 HK$1,516
HK$2,479 total
includes taxes & fees
19 Oct - 20 Oct
Entire 3 Bedroom Cozy Unit
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
Smart TV, fireplace, table football, video library
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
9.8 out of 10, Exceptional, (18)
"Love the location. The owner even decorated for us as we were coming in for our son’s Navy graduation. Highly recommend this home. "
The price is HK$3,303
HK$5,464 total
includes taxes & fees
22 Oct - 23 Oct
Navy Graduation ~ 6 Flags ~ Bristol Renaissance Faire ~ Casino ~ Outlet Malls
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior
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
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
Property grounds
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
9.4 out of 10, Exceptional, (95)
"We had a family crew of close to 20 people. We really enjoyed fishing off the pier, playing baseball in the big yard, kayaking out to the open lake, and just hanging out in the open kitchen/living room. Would recommend for big groups. Great host, quick responses."
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Interior
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
9.2 out of 10, Wonderful, (48)
"The house on Lake Elizabeth was wonderful. We had a total of 12 family members join us for a mini-vacation. We rented a pontoon boat from Twin Lakes Boat Rental, which added to the fun. The house was very nice with plenty of room for all of us and plenty of extra "toys," such as bikes, paddle boards, kayaks, pool table, etc. Jeff was very responsive to my questions and he gave us good suggestions on things to do and places to visit. "
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Lakefront Cottage with Gorgeous Sunsets
Pool
Lakefront Cottage with Gorgeous Sunsets
9.2 out of 10, Wonderful, (5)
"Simple, minimal, quaint cozy lake cottage with stunning views both day and night. Owner was very responsive and accommodating! Thanks for helping make our Christmas trip great."
Lakefront Cottage with Gorgeous Sunsets
Enjoy Beachfront Living With family!
On the beach, beach towels
Enjoy Beachfront Living With family!
9.8 out of 10, Exceptional, (66)
"What a beautiful house and right across from the lake. Plenty of room for the 9 of us tp spread out if we wanted."
Enjoy Beachfront Living With family!
Serene Lakefront Escape: Boat Dock & Grill!
Property grounds
Serene Lakefront Escape: Boat Dock & Grill!
10.0 out of 10, Exceptional, (16)
"Perfect spot for a quiet weekend getaway. House was pleasant, clean and spacious. Great view of the lake from the lower deck while you sit by the fire pit. Perfect spot for an intimate weekend with your spouse or a chill weekend with friends. "
Serene Lakefront Escape: Boat Dock & Grill!
Dog-friendly lakefront home with water toys, firepit, 2 kitchens, & 2 W/Ds
Property grounds
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
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Fridge, microwave, oven, stovetop
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
10.0 out of 10, Exceptional, (3)
"This was an amazing house. The beds were comfortable and the rooms were nice and spacious. My family and I truly enjoyed the homeliness of this vacation home. We wanted to visit downtown Chicago and this was about an hour away from downtown. Great neighborhood to stay in, we felt very safe and comfortable here. The host was also great and replied right away to questions we had. Check-in and check-out process went very smoothly!"
Gurnee Getaway: Modern Oasis Near Six Flags & Naval Base!
Beautiful Spacious Escape On The Chain O'Lakes
Outdoor dining
Beautiful Spacious Escape On The Chain O'Lakes
9.4 out of 10, Exceptional, (55)
"Everyone enjoyed the view "
Beautiful Spacious Escape On The Chain O'Lakes
Lake/Beach Getaway (Remodeled)
Property grounds
Lake/Beach Getaway (Remodeled)
10.0 out of 10, Exceptional, (23)
"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 HK$933
HK$1,725 total
includes taxes & fees
27 Oct - 28 Oct
Lake/Beach Getaway (Remodeled)
Don't see what you're looking for?
See all available properties in Pleasant Prairie
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other types of properties in Pleasant Prairie you may be interested in

Days Inn by Wyndham Pleasant Prairie Kenosha
Premium bedding, desk, laptop workspace, iron/ironing board
Days Inn by Wyndham Pleasant Prairie Kenosha
2.5 star property
7.2 out of 10, Good, (230)
"Yup"
The price is HK$463
HK$525 total
includes taxes & fees
20 Oct - 21 Oct
Days Inn by Wyndham Pleasant Prairie Kenosha
Doubletree by Hilton Pleasant Prairie Kenosha
Reception
Doubletree by Hilton Pleasant Prairie Kenosha
4.0 star property
8.8 out of 10, Excellent, (829)
"Ryan and the rest of the staff are awesome "
The price is HK$819
HK$930 total
includes taxes & fees
13 Oct - 14 Oct
Doubletree by Hilton Pleasant Prairie Kenosha
Fairfield Inn & Suites Kenosha Pleasant Prairie
Exterior
Fairfield Inn & Suites Kenosha Pleasant Prairie
2.5 star property
9.2 out of 10, Wonderful, (553)
"Always clean, staff is friendly, especially the woman who keeps the breakfast stocked."
The price is HK$654
HK$742 total
includes taxes & fees
27 Oct - 28 Oct
Fairfield Inn & Suites Kenosha Pleasant Prairie
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.

Frequently asked questions

Can I find holiday rentals in Pleasant Prairie?

Yes, there are holiday rentals in Pleasant Prairie close to Jelly Belly Center, or you can select a more secluded option if you're looking for 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 are some of the best holiday rentals that Pleasant Prairie has to offer?

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

How many holiday rentals are there in Pleasant Prairie?

With 5 Expedia holiday rentals, you're guaranteed 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 wider area, you’ll find popular places such as Naval Base Great Lakes and Six Flags Great America.

What are holiday rentals like in Pleasant Prairie?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pleasant Prairie. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from shared hotel lifts and busy front desks while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which makes a holiday rental a popular choice for family trips.