Pleasant Prairie Vacation Rentals from CA $176: Short-Term Rentals for 2025

Q: 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.

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Vacation Rentals in Pleasant Prairie

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

"A truly amazing, beautiful, and peaceful place to vacation! Would highly recommend; great experience for the price. "

Enjoy cooking and dining in this well-equipped kitchen with a gas stove, sink, and dining table.

"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."

CA $496 total

includes taxes & fees

Jul 28 - Jul 29

Relax in a spacious room with high ceilings and large windows, featuring a comfortable seating area and a crib for a family-friendly stay.

"Amazing property!! Great location communication with owners throughout our stay. This made our stay with our sailor perfect."

"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!"

Docked at the marina, the FRECKLED FIN awaits your arrival.

"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."

CA $304 total

includes taxes & fees

Aug 4 - Aug 5

Relax in this spacious living room with a large L-shaped sofa, smaller sofa, and chaise lounge.

"Had fun"

Relax on the patio with a comfortable sectional sofa and enjoy a barbecue.

"We were really looking forward to the stay, and it exceeded our expectations significantly. I appreciate how they turned a small house that could have just been a bit rundown into a very lovely space all around. "

CA $364 total

includes taxes & fees

Aug 11 - Aug 12

Enjoy meals in this dining room with a large table and six chairs, a vase with flowers, and a comfortable rug.

"Great experience, lots of cooking materials "

CA $421 total

includes taxes & fees

Jul 27 - Jul 28

CA $392 total

includes taxes & fees

Jul 27 - Jul 28

Relax in this stylish living area with a round dining table, comfortable sofa, and flat-screen TV.

"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!"

Enjoy the serene views from the balcony of this two-story home, which features a pool and large windows.

"Great place to stay! "

CA $1,379 total

includes taxes & fees

Jul 27 - Jul 28

Enjoy a bright and airy space with a dining area for two, large windows, and sliding glass doors leading to an outdoor deck.

"wonderful experience from beginning to end"

"Happy Place, immaculate, well designed, nice mattress, fun easy place with friends"

Relax in a serene oceanfront setting with a hammock and lush greenery.

"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!"

Start your day with a warm cup of coffee at the in-room coffee station.

"Close to our family and friends. "

Relax in this inviting living area with a high ceiling, comfortable sofa, and a beautiful view.

"The home was good. We had some problems but nothing major. Will stay again if we happen to go to Chicago again"

"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."

Enjoy outdoor cooking on the porch with a barbecue grill and take in the charm of this two-story home.

"One of my favorite places I've stayed at "

Enjoy cooking in this well-equipped kitchen with a microwave, stove, and oven.

"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."

Relax in this stylish living room with a beige sofa, L-shaped sectional, and fireplace.

"Came for Navy event and had a good night's rest"

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Top Pleasant Prairie Hotel Reviews

Motel 6 Libertyville, IL

10/10 Excellent

"Tv didn’t work "

Great Wolf Lodge Illinois

10/10 Excellent

"The best hotel I have stayed in by far. Worth every single penny the amount of activities they have for the kids included and everything you might need right in the property no need to even go anywhere else. I will definitely book with them again and again. In love with the hotel. Dunkin, restaurant, Ice cream shop, pizza shop, build a bear, rock climbing so much I can keep going. Don’t think about it twice just book. "

Illinois Beach Hotel

10/10 Excellent

"This is a great vacation spot for people who are not fans of big crowds. The hotel was very nice, quite clean, with a helpful staff. The beach was great and not crowded at all. It's sandy with a bit of small rocks as you wade in, so if your feet are sensitive, it might be good to wear water shoes. The water was cold, but we got used it easily. The rooms come with a microwave and fridge, so we brought our own food for breakfast and lunch. We ate at Nolan's, the restaurant on site, for dinner each day. The food was delicious and the staff were so friendly. Despite all of the sand and water we tried not to track in from the beach, the lobby is quite clean, and a relaxing place to sit. We also sat in the courtyard by a fire, which was enjoyable. This was our first time at Illinois Beach State Park and at this hotel. It won't be our last. This will be a yearly vacation destination for us!"

Find out more about Pleasant Prairie

Everything you need to know about Pleasant Prairie vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Pleasant Prairie vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Pleasant Prairie vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Pleasant Prairie vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Pleasant Prairie. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Pleasant Prairie vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Pleasant Prairie vacation rentals we have selected for you start as low as CA $176 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Pleasant Prairie rentals

At Expedia, we put the best Pleasant Prairie vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Pleasant Prairie rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Pleasant Prairie vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Pleasant Prairie. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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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?

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.

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Pleasant Prairie Vacation Rentals

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Vacation Rentals in Pleasant Prairie

Modern Lakeside Villa

Modern Lakeside Villa

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

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

Riverfront Libertyville Retreat w/ Outdoor Kitchen

Riverfront Libertyville Retreat w/ Outdoor Kitchen

Steps to Powers Lake: Wisconsin Family Home

Steps to Powers Lake: Wisconsin Family Home

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

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

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

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

3-bedroom vacation home just a short walk to Lake Michigan

3-bedroom vacation home just a short walk to Lake Michigan

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base

Tiny Home Retreat with hot tub

Tiny Home Retreat with hot tub

Newly Remodeled in Pistakee Bay on the Chain O' Lakes

Newly Remodeled in Pistakee Bay on the Chain O' Lakes

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

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.

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

Rustic Riverside A-Frame Retreat: Secluded Charm.

Rustic Riverside A-Frame Retreat: Secluded Charm.

Scenic Waterfront Lake Michigan Escape

Scenic Waterfront Lake Michigan Escape

Roxan Corner

Roxan Corner

Entire Beautiful Grove Home

Entire Beautiful Grove Home

North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar

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!!

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

Large Group Retreat w/ secluded party room and private pool

Large Group Retreat w/ secluded party room and private pool

Entire 3 Bedroom Cozy Unit

Entire 3 Bedroom Cozy Unit

Top Pleasant Prairie Hotel Reviews

Motel 6 Libertyville, IL

Find out more about Pleasant Prairie

Find out more about Pleasant Prairie

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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Frequently asked questions