Pleasant Prairie Vacation Rentals

Check prices for these dates

In two weeks
Sep 12 - Sep 14
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23
In four months
Dec 19 - Dec 21

Vacation Rentals in Pleasant Prairie

Modern Lakeside Villa
Outdoor spa tub

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
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

9.6 out of 10, Exceptional, (4)
"Home was cute and as advertised, outdoor area great for families to relax. Only recommendation to have some information at the home for guests in the event the alarm system is activated so it can be acknowledged quickly. "
North Chi Retreat-Near Navel base-Sauna,Pool, Airhokey, grill,King bed,Tikki Bar
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Smart TV, music library, video library, stereo

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

9.0 out of 10, Wonderful, (32)
"Had fun"
Comfortable 2 bedroom house near Great Lakes Navy Base ideal for families
Charming 3-bedroom house in Grayslake
Fridge, microwave, oven, stovetop

Charming 3-bedroom house in Grayslake

9.8 out of 10, Exceptional, (16)
"Fells like home very cozy calm area definitely a get away relaxing place "
$477 nightly
The price is $506
Sep 1 - Sep 2
Total with taxes and fees
Charming 3-bedroom house in Grayslake
Marina Life II - 28 Carver @ Reef Point Marina
Property grounds

Marina Life II - 28 Carver @ Reef Point Marina

9.6 out of 10, Exceptional, (45)
"We stayed for two nights at the house boat. The host communicated very efficiently and was nice. Even though the boat is small, it was cozy and we never felt cramped. We loved the amenities that are included in the marina. Walking distance from downtown so there was plenty to do. Would stay here again. "
$229 nightly
The price is $242
Aug 31 - Sep 1
Total with taxes and fees
Marina Life II - 28 Carver @ Reef Point Marina
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Interior

Riverfront Libertyville Retreat w/ Outdoor Kitchen

8.6 out of 10, Excellent, (30)
"Thank you very much"
Riverfront Libertyville Retreat w/ Outdoor Kitchen
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Dining

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

10.0 out of 10, Exceptional, (84)
"Was here for a funeral. Good place to stay and relaxing."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
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, (89)
"We loved the beach the kids could have stayed there all day! Fishing was wonderful too! Such a fun house!"
Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!
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, (210)
"Great place to stay! "
$800 nightly
The price is $844
Sep 1 - Sep 2
Total with taxes and fees
7 1/2 Acre Estate, Fishing Pond, Events! Discounts! Weddings, Heated pool
Beautiful and spacious lakefront home! Close to everything!
Exterior detail

Beautiful and spacious lakefront home! Close to everything!

9.6 out of 10, Exceptional, (48)
"Overall nice stay, the master shower didn’t work but there were 2 other bathrooms, "
Beautiful and spacious lakefront home! Close to everything!
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, (241)
"What an incredible stay! The house was clean and organized. The open floor plan had lots of good spaces for family to gather. The views and property overall was beautiful! "
The Retreat on Lake Michigan Spectacular 6 bd/4bth 4000 sqft
Entire 3 Bedroom Cozy Unit
Smart TV, books

Entire 3 Bedroom Cozy Unit

9.6 out of 10, Exceptional, (21)
"This property was comfortable and convenient for our attendance at the Navy boot camp graduation. "
Entire 3 Bedroom Cozy Unit
Beautiful Spacious Escape On The Chain O'Lakes
Outdoor dining

Beautiful Spacious Escape On The Chain O'Lakes

9.2 out of 10, Wonderful, (61)
"Beautiful location, easy access. Could use carpet replaced, bed in large bedroom replaced. Otherwise we had a good stay."
Beautiful Spacious Escape On The Chain O'Lakes
Lake Front 2.20 acre estate Private boat launch with pier
Interior

Lake Front 2.20 acre estate Private boat launch with pier

9.8 out of 10, Exceptional, (16)
"We had a great family vacation here! The property is huge & beautiful. Tons of large clean bedrooms & baths & great rooms. Played pool, foisball & ping pong in garage, pickleball & basketball on court, volleyball & teetherball. This place had everything we were looking for!"
Lake Front 2.20 acre estate Private boat launch with pier
🌲☀️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, (53)
"Great space Great Lake view! Lots to do for family entertainment…basketball billiards ping pong plus much much more. "
🌲☀️Private Lakefront prop. with Kayaks, Paddle boards, boat rental PVT dock☀️🌲
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
Outdoor dining

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

10.0 out of 10, Exceptional, (9)
"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."
$1,758 nightly
The price is $1,863
Sep 22 - Sep 23
Total with taxes and fees
Feels like you are on vacation. Comfortable cozy! Like a breath of fresh air.
A Diamond in the Rough
Outdoor dining

A Diamond in the Rough

9.4 out of 10, Exceptional, (90)
"I will be staying here again in the future. Great place at a great location."
A Diamond in the Rough
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, (4)
"We stayed for two nights and absolutely loved it! The space was cozy and welcoming, and my family felt right at home. The second-floor patio was stunning—we spent both days out there just soaking it all in. The kitchen was beautiful and had everything we needed. Overall, such a wonderful experience and we’d love to come back!"
Big Blue Lakehouse - Shared Pier, Lake Mary Access, Stunning Lake Views, Grill, Firepit, Pool Table
Cozy RV in our land with community private beach, fire pit, bring your boat.
Property grounds

Cozy RV in our land with community private beach, fire pit, bring your boat.

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a nice time visiting Antioch, IL. The property clean, quiet and well maintained. The camper was adorable and very comfortable. Thank you!"
Cozy RV in our land with community private beach, fire pit, bring your boat.
🌲☀️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, (106)
"Was a great place to stay for our bachelorette trip! "
🌲☀️Private Lakefront prop. With Kayaks And Paddleboard Boat Rental Optional☀️🌲
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

Top Pleasant Prairie Hotel Reviews

Find out more about Pleasant Prairie

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Pleasant Prairie in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $242 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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?

Fabulous Lake House near Lake Geneva, 1.5 hours from Chicago!!: This vacation home rental outside of Pleasant Prairie is located on a lake and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

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.