Pleasant Prairie Vacation Rentals

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Jul 31 - Aug 1
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Aug 1 - Aug 2
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Aug 1 - Aug 3
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Aug 8 - Aug 10

Vacation Rentals in Pleasant Prairie

Modern Lakeside Villa
Relax in the hot tub surrounded by ocean views and Adirondack chairs.

Modern Lakeside Villa

10.0 out of 10, Exceptional, (19)
"A truly amazing, beautiful, and peaceful place to vacation! Would highly recommend; great experience for the price. "
Modern Lakeside Villa
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Enjoy cooking and dining in this well-equipped kitchen with a gas stove, sink, and dining table.

3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi

9.0 out of 10, Wonderful, (7)
"We stayed here for my son’s Navy boot camp graduation, and overall it was a great experience. The home was clean and had everything we needed. The area was okay and felt safe. Communication with the owner was smooth—she responded quickly and was very helpful. The location was super convenient, only about 10 minutes from the base. I would definitely recommend this place for anyone attending a graduation or visiting the area."
The price is ￥27,469
￥53,913 total
includes taxes & fees
Aug 12 - Aug 13
3BR Apartment, Split level house, in Waukegan, 7min. to The Naval Base with WiFi
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Relax in a spacious room with high ceilings and large windows, featuring a comfortable seating area and a crib for a family-friendly stay.

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (29)
"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Steps to Powers Lake: Wisconsin Family Home
Terrace/patio

Steps to Powers Lake: Wisconsin Family Home

10.0 out of 10, Exceptional, (2)
"This lake house was everything we hoped for and more! The property was spotless, beautifully maintained, and surrounded by stunning views. The fishing was incredible—we caught something every day right off the dock. It was the perfect mix of relaxation and outdoor fun; we can’t wait to come back!"
Steps to Powers Lake: Wisconsin Family Home
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Docked at the marina, the FRECKLED FIN awaits your arrival.

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

9.2 out of 10, Wonderful, (11)
"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 ￥20,045
￥33,053 total
includes taxes & fees
Aug 12 - Aug 13
Reef Point Marina - Vessel: "Freckled Fin" - East Dock 1, Slip 19
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Relax in this spacious living room with a large L-shaped sofa, smaller sofa, and chaise lounge.

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

9.0 out of 10, Wonderful, (31)
"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
Relax on the patio with a comfortable sectional sofa and enjoy a barbecue.

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 ￥17,372
￥36,912 total
includes taxes & fees
Aug 12 - Aug 13
3-bedroom vacation home just a short walk to Lake Michigan
Quaint Bungalow, near Great Lakes Naval Base
Enjoy meals in this dining room with a large table and six chairs, a vase with flowers, and a comfortable rug.

Quaint Bungalow, near Great Lakes Naval Base

10.0 out of 10, Exceptional, (61)
"Great experience, lots of cooking materials "
The price is ￥20,045
￥46,029 total
includes taxes & fees
Aug 12 - Aug 13
Quaint Bungalow, near Great Lakes Naval Base
Tiny Home Retreat with hot tub
Outdoor dining

Tiny Home Retreat with hot tub

The price is ￥19,154
￥42,911 total
includes taxes & fees
Aug 12 - Aug 13
Tiny Home Retreat with hot tub
Newly Remodeled in Pistakee Bay on the Chain O' Lakes
Relax in this stylish living area with a round dining table, comfortable sofa, and flat-screen TV.

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
Marina Life II - 28 Carver @ Reef Point Marina
Relax in the spacious seating area with a clear view of the marina and water beyond.

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (43)
"This is a super fun place to stay! The marina has excellent amenities and the boat was clean and well appointed."
The price is ￥22,272
￥35,702 total
includes taxes & fees
Aug 12 - Aug 13
Marina Life II - 28 Carver @ Reef Point Marina
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Enjoy the serene views from the balcony of this two-story home, which features a pool and large windows.

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

9.8 out of 10, Exceptional, (208)
"Great place to stay! "
The price is ￥86,861
￥149,442 total
includes taxes & fees
Aug 12 - Aug 13
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Enjoy a bright and airy space with a dining area for two, large windows, and sliding glass doors leading to an outdoor deck.

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

10.0 out of 10, Exceptional, (82)
"Very nice home very cozy beautiful view"
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Rustic Riverside A-Frame Retreat: Secluded Charm.
Smart TV, fireplace

Rustic Riverside A-Frame Retreat: Secluded Charm.

10.0 out of 10, Exceptional, (13)
"Happy Place, immaculate, well designed, nice mattress, fun easy place with friends"
Rustic Riverside A-Frame Retreat: Secluded Charm.
Scenic Waterfront Lake Michigan Escape
Relax in a serene oceanfront setting with a hammock and lush greenery.

Scenic Waterfront Lake Michigan Escape

10.0 out of 10, Exceptional, (11)
"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
Start your day with a warm cup of coffee at the in-room coffee station.

Roxan Corner

8.4 out of 10, Very Good, (35)
"Close to our family and friends. "
Roxan Corner
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar
Property grounds

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
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Enjoy outdoor cooking on the porch with a barbecue grill and take in the charm of this two-story home.

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

9.8 out of 10, Exceptional, (88)
"One of my favorite places I've stayed at "
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
Large Group Retreat w/ secluded party room and private pool
Enjoy cooking in this well-equipped kitchen with a microwave, stove, and oven.

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
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Relax on the deck with a comfortable table and chairs, surrounded by lush plants and a stylish rug.

Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.

10.0 out of 10, Exceptional, (7)
"We enjoyed our stay at the house. The open spaces and high ceilings made the space feel special. Would love to reserve the space again in the future."
The price is ￥150,995
￥238,956 total
includes taxes & fees
Aug 18 - Aug 19
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
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

Baymont Inn & Suites by Wyndham Richmond

Baymont Inn & Suites by Wyndham Richmond

10/10 Excellent
"Very attentive friendly staff, excellent free breakfast, decent room, the fitness room is tiny but was okay. "
Leila 2-night trip
Posted 1 day ago
Baymont Inn & Suites by Wyndham Richmond

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?

Riverfront Libertyville Retreat w/ Outdoor Kitchen: This vacation home rental outside of Pleasant Prairie offers a balcony, a selection of games, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

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 Naval Base Great Lakes and Six Flags Great America.

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.