Pleasant Prairie Vacation Rentals

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Vacation Rentals in Pleasant Prairie

Terrace/patio
Modern Lakeside Villa
10.0 out of 10, Exceptional, (11)
"We (wife and I) spent 2 nights here as a get-away/Christmas gift to each other, and it was beyond expectations! The location is in a quiet area and close to Kenosha for the shops and restaurants. The views are stunning, and we spent most of our time watching the waves and enjoying “unplugged” time. The house is beautifully decorated and spacious for two people."
Modern Lakeside Villa
Outdoor pool, a heated pool
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
9.8 out of 10, Exceptional, (178)
"Lots to do, lots of space, very cool property"
Heated Pool, Hot Tub, Fishing Pond, Game Room, Events Allowed! Read Description
Property grounds
Unique and Charming Private Quarters
10.0 out of 10, Exceptional, (34)
"Sandy does a nice job of welcoming you, with her friendliness and her creative expression seen in every detail of her home. It was a very comfortable stay in all aspects. My one caution, which she has stated, is it is an upstairs apartment, so it is not handicap accessible in any way."
The price is ¥8,501
per night
May 22 - May 23
Unique and Charming Private Quarters
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Property grounds
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (39)
"Quaint and very clean."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Smart TV, stereo
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
9.6 out of 10, Exceptional, (8)
"The proximity to Great Lakes Recruitment Center, Sarge’s Meet & Greet, restaurants, etc. is perfect. We were in town for our son’s boot camp graduation and knew we wanted more room to hang out than a typical hotel room would offer. It was great to be able to relax, watch movies, just hang out with our sailor for the precious two days we had. This place has location, location, location if you’re coming in for boot camp graduation."
The price is ¥18,702
per night
May 19 - May 20
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Private kitchen
Fully Updated home. Great for the entire family!
7.6 out of 10, Good, (10)
"My impression of the inside was good. However the outside needs some work. Maybe some up grades in the furniture would be beneficial. Other then that it was an enjoyable experience Thank u"
Fully Updated home. Great for the entire family!
Terrace/patio
Get lost from the hustle. Peaceful nature, country living at its finest.
10.0 out of 10, Exceptional, (16)
"Owners make sure you have everything necessary!"
Get lost from the hustle. Peaceful nature, country living at its finest.
TV
New Your Home Away From Home! - Near Great Lakes Naval Base!!
9.2 out of 10, Wonderful, (10)
"We were in North Chicago for PIR. It is less than 2 miles to the ceremony (we walked to avoid traffic and parking), there are ample rooms and beds for a family crew. Space to cook and serve and lounge about while your sailor decompresses. Restaurants are near enough (we got pizza from LouMalnatis in Gurnee), and grocery stores were close too. Communication was spot on, every time I had a question, they were on top of it (no issues, just questions)"
New Your Home Away From Home! - Near Great Lakes Naval Base!!
TV, books
Quaint Bungalow, near Great Lakes Naval Base
10.0 out of 10, Exceptional, (45)
"This is one of the most charming vrbo that i have stayed at. the house is just as 1 described My son graduated Navy Bootcamp and it was so nice to have the comfort of this home vs sharing 3 hotel rooms."
The price is ¥20,866
per night
May 20 - May 21
Quaint Bungalow, near Great Lakes Naval Base
Property grounds
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
10.0 out of 10, Exceptional, (62)
"Beautiful, spectacular mornings with the sunrise and the view of the lake. The house is very comfortable. The kitchen is very nice. We were able to prepare all our family meals."
Stunning Lakefront Home on the Chain O'Lakes! ★ Amazing Views & Newly Rehabbed
Exterior
1929 charmer
The price is ¥18,393
per night
May 19 - May 20
1929 charmer
Property grounds
The Beach Life!— Newly Renovated Beach Home awaits you!
10.0 out of 10, Exceptional, (14)
"Don’t be fooled by the modest exterior—the renovated interior of this house is charming and cozy. The owners have gone out of their way to provide the most comfortable bedrooms and fully equipped kitchen. There was autumn decor, new fleece blankets for snuggling, and 3 big TVs. Just a few hundred feet from a huge, clean beach, we also enjoyed the Racine Zoo, giant playground, board games, nearby haunted houses, and local eats. A friendly, diverse neighborhood great for a quiet but enjoyable...
The Beach Life!— Newly Renovated Beach Home awaits you!
Property grounds
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
9.6 out of 10, Exceptional, (50)
"This was a cute property and had an open and spacious feel inside. We really loved that all three rooms had a king sized bed and they were very comfortable! It was also a huge bonus that there was a second bathroom with a shower as we had to be somewhere fairly early on Saturday and everyone was able to get ready fast. The house also felt really solid and well insulated so each room felt like it had enough privacy. We would definitely stay here again!"
Fox Lake "Funcation" ★ 3 King Beds ★ Chain O Lakes
View from property
Beautiful and spacious lakefront home! Close to everything!
9.8 out of 10, Exceptional, (24)
"It was so much fun we had a great time!"
Beautiful and spacious lakefront home! Close to everything!
Private kitchen
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
6.8 out of 10, (3)
"The home is very cute, nice location, and overall was fine for what we needed. We were in town for a wedding and needed a dog friendly place where he could hang while we were gone, and basically just a place to crash. The host was very responsive and let us check in early which was so helpful. The fenced in yard was great! But, it wasn’t the cleanest place I’ve ever stayed. The tub had bugs in it and was definitely dirty. Thankfully we didn’t need to use it but if we had, I would’ve had to clean...
The price is ¥26,275
per night
Jun 12 - Jun 13
Perfectly Cozy! Close to so many places. Pet friendly. Great private backyard.
Property grounds
Luxury lake home with dock, patio, and deck!
10.0 out of 10, Exceptional, (23)
"Beautiful house. Clean"
Luxury lake home with dock, patio, and deck!
Terrace/patio
Roxan Corner
9.0 out of 10, Wonderful, (18)
"This duplex was perfect for my three sons and myself. We stayed five days to attend one of my son’s Navy Graduation! House was very clean and modern. Had everything we needed, was a nice neighborhood, quiet neighbors? Close to everywhere we needed to go. Only suggestion would be to have the owners secure the rugs, they are very slippery. "
Roxan Corner
Interior
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
10.0 out of 10, Exceptional, (32)
"This house has everything you need for a great getaway! It was clean, very well-appointed, and had lots of space to spread out. The beds were comfy, the coffee bar was well stocked, and there was even a station set up with waffle mix, makers, and fixins'. Mike (property owner) responded quickly to our questions and Carrie (property manager) was delightful! There is a reason this place has so many glowing reviews...HIGHLY RECOMMEND!"
Indoor Kidquariam, Large Group Equipped, EnglishPrairieBnB
Property grounds
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
10.0 out of 10, Exceptional, (217)
"We had a great time! The house provided lots of space, loads of entertainment and opportunity for family fun. The weather was conducive for outdoor activities. All our needs and wants were met! We'll be back! Thank you!"
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Property grounds
Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach
9.8 out of 10, Exceptional, (31)
"House was great. Had everything we could ask for!!"
Luxury Lake House Steps from Browns Lake w. Arcade Room + Private Beach
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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.

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

Premium bedding, desk, laptop workspace, iron/ironing board
Days Inn by Wyndham Pleasant Prairie Kenosha
2.5 star property
7.6 out of 10, Good, (128)
"Great experience at Days Inn! Ample parking, delicious hot breakfast, and friendly staff made my stay enjoyable. Highly recommended!""
The price is ¥9,198
per night
May 22 - May 23
Days Inn by Wyndham Pleasant Prairie Kenosha
Bar (on property)
Doubletree by Hilton Pleasant Prairie Kenosha
4.0 star property
8.8 out of 10, Excellent, (794)
"I made a last minute reservation in a snowstorm; the desk staff was friendly and the wait staff in the next door restaurant excellent. The food was surprisingly good. It’s in the middle of an outlet mall by the highway but in driving distance of other attractions. Pleasant Prairie is just over the WI state line on I-94 "
The price is ¥16,291
per night
May 23 - May 24
Doubletree by Hilton Pleasant Prairie Kenosha
Reception
Super 8 by Wyndham Kenosha/Pleasant Prairie
2.0 star property
6.6 out of 10, (966)
"Good and little noisy"
The price is ¥9,583
per night
May 27 - May 28
Super 8 by Wyndham 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.

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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?

Unique and Charming Private Quarters: This vacation home rental outside of Pleasant Prairie is equipped with a garden, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave, and a coffee maker.

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.

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