Pleasant Prairie vacation rentals

We found 167 vacation rentals — enter your dates for availability

Discover a selection of vacation rentals in Pleasant Prairie that are perfect for your trip. Whether you’re staying in a vacation home with family or friends, you'll have the amenities you expect and more, which might include a garden and pool. Whatever you're looking for, you'll be sure to find a rental to meet everyone's needs, including accessible or non-smoking choices.

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Find out more about Pleasant Prairie

Why visit Pleasant Prairie

  • Family-Friendly Attractions: Enjoy the Pleasant Prairie RecPlex, offering a variety of recreational activities for all ages.
  • Beautiful Beaches and Parks: Relax at scenic beaches and urban parks, perfect for picnics and outdoor adventures.
  • Charming Neighborhoods: Explore the welcoming atmosphere and beautiful homes in the area.
  • Diverse Accommodation Options: Choose from vacation rentals, cozy cottages, and modern hotels to suit your needs.
  • Friendly Community: Experience the warm hospitality of Pleasant Prairie’s residents while creating lasting memories.

Popular types of accommodation in Pleasant Prairie

Planning a getaway to Pleasant Prairie? Discover the charm of this vibrant destination with a range of vacation rentals, including private homes, cozy cottages, and modern apartments. Whether you're searching for the best hotels or spacious suites, Pleasant Prairie offers a variety of options to suit every traveler’s needs. Explore your perfect stay and experience the best this beautiful area has to offer.

  • Houses: The top choice for visitors to Pleasant Prairie, these homes offer spacious accommodations ideal for families or groups.
  • Cottages: A delightful option for a cozy getaway, perfect for couples or small families seeking charm and comfort.
  • Apartments: Convenient and modern, apartments provide travelers with a home-like atmosphere while exploring the area.
  • Cabins: Ideal for nature enthusiasts, cabins offer a rustic escape surrounded by the beauty of the outdoors.
  • Villas: Luxurious and spacious, villas are perfect for those desiring upscale amenities and a touch of elegance during their stay.**

Top attractions near Pleasant Prairie

Pleasant Prairie, Wisconsin, offers a delightful getaway for families and city explorers alike. Enjoy a variety of attractions including urban parks, beautiful beaches, and medical centers. Whether you're looking for picnic spots, recreational activities, or scenic views, the area provides ample opportunities for outdoor adventures and urban experiences. Discover the charm of Pleasant Prairie as you create unforgettable memories with loved ones during your vacation.

  • Bristol Renaissance Faire: Experience a lively outdoor fairground that transports you to the 16th century, featuring costumed performers, artisan crafts, and delicious food. It's a perfect family-friendly atmosphere where you can enjoy live entertainment and immersive activities.
  • Simmons Island Beach: A beautiful beach offering a relaxing escape with soft sand and stunning views of Lake Michigan. Ideal for sunbathing, picnicking, and enjoying beach vibes with family and friends.
  • Aurora Medical Center Kenosha: While primarily a medical facility, this center reflects a commitment to family health and community well-being, showcasing advanced healthcare services in a welcoming environment.

Things to do recommended for couples

Discover a romantic getaway in Pleasant Prairie. Enjoy a scenic walk at the picturesque Lake Andrea, indulge in a couples' massage at a local spa, or savor a candlelit dinner at one of the charming restaurants. Make unforgettable memories together in this delightful destination.

Things to do recommended for families

Families can explore the scenic trails at the Prairie Springs Park, enjoy a fun day at the Pleasant Prairie Premium Outlets for shopping, or visit the nearby Jelly Belly Warehouse for a sweet factory tour. Each activity offers unique experiences perfect for creating lasting memories.

Things to do recommended for groups

Explore the scenic trails at Prairie Springs Park or enjoy a fun-filled day at the Pleasant Prairie Premium Outlets. For a unique experience, consider a group outing at the nearby Jelly Belly Factory for a sweet tour and tasting adventure.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Pleasant Prairie

When planning your trip—whether you're traveling with a group, family, pets, or seeking extended stays—be sure to prioritize your filters accordingly. Here are some helpful Vrbo booking tips to consider.

  • Traveling to Pleasant Prairie with a group: Think about how many bedrooms you'll require, as well as any amenities like a complete kitchen or outdoor area for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Pleasant Prairie with young kids: Traveling with young kids can be quite a task. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Pleasant Prairie: For many, a family vacation isn't truly complete without their furry companion by their side. If that resonates with you, explore Vrbo listings that welcome pets. Most pet-friendly properties offer amenities like feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Pleasant Prairie: If you're seeking vacation rentals with special offers for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search for the perfect accommodation.

Where to stay near Pleasant Prairie

Explore the charming city of Pleasant Prairie, Wisconsin, where family-friendly vibes and a welcoming atmosphere await. Discover the Pleasant Prairie RecPlex for recreational fun, or enjoy a relaxing springtime getaway amidst beautiful homes. With nearby cities offering a blend of business and budget-friendly experiences, Pleasant Prairie is the perfect destination for a diverse vacation. Enjoy the friendly people and create lasting memories in this delightful region of the United States.

  • Kenosha: Kenosha is a vibrant city located 6 miles from Pleasant Prairie, offering a delightful mix of outdoor scenery and romantic experiences. Visitors can explore its beautiful lakeside parks and take leisurely strolls along the beach. The city is home to various recreational areas and educational attractions, making it perfect for families and couples alike. Popular spots include the scenic Lake Michigan shoreline and the nearby national state park, where nature enthusiasts can hike and enjoy breathtaking views. Kenosha's lively shopping centers add to the travel experience, providing a blend of local boutiques and national retailers.
  • Woodworth: Situated just 3 miles away from Pleasant Prairie, Woodworth is a charming village that invites travelers to embrace its serene outdoor and romantic atmosphere. Known for its recreation park, Woodworth offers a peaceful setting for picnics, leisurely walks, or simply enjoying nature. The village is surrounded by tranquil urban parks, picturesque lakes, and inviting beaches, making it an ideal spot for relaxation and reconnecting with nature. Whether you're looking to unwind or enjoy a day of outdoor activities, Woodworth provides a delightful escape from the hustle and bustle of city life.
  • Gurnee: Gurnee is an exciting city located 13 miles from Pleasant Prairie, renowned for its family-friendly and entertainment-themed attractions. This bustling destination features a variety of shopping centers and a large shopping mall, perfect for a fun day of retail therapy. Thrill-seekers will love the nearby theme park and waterpark, which offer exhilarating rides and water attractions for all ages. With its vibrant atmosphere and numerous entertainment options, Gurnee is a fantastic place for families to create lasting memories while enjoying the excitement of city life.

Best time to go to Pleasant Prairie

If you're planning a trip to Pleasant Prairie, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January23.2°F (-4.9°C)Light RainMostly CloudyAverageAverage
February24.8°F (-4.0°C)Light RainMostly CloudyAverageSlightly Low
March35.2°F (1.8°C)Light RainMostly CloudyAverageSlightly Low
April43.9°F (6.6°C)Light RainMostly CloudySlightly HighSlightly Low
May54.5°F (12.5°C)Light RainMostly SunnyAverageAverage
June64.8°F (18.2°C)Light RainMostly SunnySlightly HighSlightly High
July71.4°F (21.9°C)Light RainMostly SunnySlightly HighSlightly High
August70.9°F (21.6°C)Light RainMostly SunnyAverageSlightly High
September64.8°F (18.2°C)Light RainMostly SunnyAverageAverage
October52.5°F (11.4°C)Light RainMostly SunnySlightly LowAverage
November40.1°F (4.5°C)Light RainMostly SunnySlightly LowAverage
December30.7°F (-0.7°C)Light RainMostly CloudySlightly LowAverage

Booking with Vrbo is a breeze

Looking to save on your next vacation? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, booking a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Save more with One Key

Reserve an eligible Vrbo for your group getaway and collect all the OneKeyCash from your booking. Being the planner has its perks. By enrolling in our travel rewards program, One Key, you can immediately access member discounts and earn as well as redeem OneKeyCash on qualifying bookings. Sign up today to start enjoying your savings.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers an easy-to-use platform for planning your travels. You can create new trips, resume planning from where you left off, or organize and view your existing plans all in one place. Your saved or booked properties will be organized under categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The lakeside setting of Pleasant Prairie is ready to explore

Enjoy the temples and other features of Pleasant Prairie. This city's shopping, restaurants and lake draw many visitors. Naval Base Great Lakes and Six Flags Great America are just a couple of the must-sees in the area. Whether you're planning a family vacation, friends trip or romantic retreat, Vrbo has a great selection of vacation homes. Many rentals come with a full kitchen and separate dining area, perfect if you need a space for entertaining.

Activities and attractions in and around Pleasant Prairie

Are you looking for attractions to see during your stay? Venture out of your cozy vacation rental and experience everything that makes Pleasant Prairie a fun place to get away. Here are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city center:

  • Six Flags Great America (12.8 mi / 20.6 km)
  • Jelly Belly Center (2.8 mi / 4.4 km)
  • Great Wolf Lodge Water Park (11.7 mi / 18.9 km)
  • Racine Zoological Gardens (15.6 mi / 25.1 km)
  • Jet Funn (16.3 mi / 26.3 km)
  • Asylum Skate Park (17.9 mi / 28.8 km)

Exploring the natural features in Pleasant Prairie

Whether you're looking for exciting outdoor activities or just want to appreciate the scenery, Pleasant Prairie is a great place to spend some time outside. These are some of the area's most eye-catching features, all within 30 miles (48.2 km) of the city center:

  • Simmons Island Beach (6.7 mi / 10.7 km)
  • Waukegan SportsPark (9.5 mi / 15.3 km)
  • Silver Lake Beach (10.8 mi / 17.3 km)
  • Wilmot Mountain (13.8 mi / 22.2 km)
  • Franksville Park (14.1 mi / 22.7 km)
  • Waukegan Harbor (14.3 mi / 23 km)

Transportation to and around Pleasant Prairie

The nearest airport is in Kenosha, WI (ENW-Kenosha Regional), located 2.9 mi (4.6 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into General Mitchell Intl. Airport (MKE), which is 27.4 mi (44 km) away.

Frequently asked questions

What is the best area to stay in Pleasant Prairie, Wisconsin, United States of America when booking a vacation rental?
When considering the best area to stay in Pleasant Prairie, Wisconsin, for a vacation rental, the Pleasant Prairie area itself is a fantastic choice. This neighborhood offers a blend of tranquility and accessibility, making it ideal for both relaxation and exploration. One of the highlights of staying here is the close proximity to the beautiful Lake Andrea, which is superb for outdoor activities such as fishing, kayaking, and picnicking.

Another top attraction nearby is the Pleasant Prairie Premium Outlets, a shopper's paradise featuring a variety of brand-name stores and dining options. The area has a good number of vacation rental properties, ranging from cozy homes to spacious rooms, ensuring that you can find something that fits your needs.
How much does it cost to rent a vacation home in Pleasant Prairie?
Prices for vacation rentals in Pleasant Prairie vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Pleasant Prairie to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Pleasant Prairie vacation house rentals?
You can find great discounts on house rentals in Pleasant Prairie on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Pleasant Prairie?
In Pleasant Prairie, vacation houses are the most popular type of rental accommodation, with several options available throughout the area. These properties typically feature spacious layouts, multiple bedrooms, fully equipped kitchens, and inviting living areas, making them ideal for families or groups looking to enjoy a comfortable stay. Many of these homes also come with outdoor patios or yards, superb for relaxing after a day of exploring the beautiful surroundings.
Are there any family house rentals in Pleasant Prairie?
In Pleasant Prairie, Wisconsin, there are several family-friendly house rentals available, making it a great choice for those traveling with kids. The area features spacious homes that often include amenities such as full kitchens, cozy living rooms, and outdoor spaces where children can play. Many properties also provide conveniences like laundry facilities and Wi-Fi, ensuring a comfortable stay for families.

Visitors to Pleasant Prairie can enjoy nearby attractions, including the scenic landscapes of Lake Michigan, which offers opportunities for swimming, picnicking, and nature walks. The local parks are ideal for families looking to engage in outdoor activities, while shopping and dining options are conveniently located in the area.
Can I find long-stay vacation rentals in Pleasant Prairie?
A long-stay vacation rental in Pleasant Prairie is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Pleasant Prairie?
In Pleasant Prairie, travelers will find several pet-friendly house rentals that cater to those looking to enjoy a getaway with their furry companions. Many of these homes come equipped with amenities such as spacious backyards, fully stocked kitchens, and comfortable living spaces, ensuring a relaxing stay.

The area is conveniently located near several parks, providing ample opportunities for outdoor activities with pets. The picturesque Prairie Springs Park features walking trails, open green spaces, and a lake, making it an ideal spot for leisurely strolls or picnics with your dog. Additionally, the nearby Lake Andrea offers scenic views and a friendly setting for pet owners.
Are there any remote work vacation rentals in Pleasant Prairie?
In Pleasant Prairie, Wisconsin, there are several vacation rentals suitable for remote work. Many of these properties come equipped with amenities that facilitate productivity, such as high-speed internet, dedicated desk spaces, and comfortable living areas. Travelers can expect accommodations that include free Wi-Fi, allowing for seamless connectivity during their stay.

The area is conveniently located near the scenic shores of Lake Michigan, offering opportunities for outdoor relaxation after work hours. Nearby points of interest, like the pleasant parks and local dining options, enhance the overall experience for those balancing work and leisure. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Pleasant Prairie vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Pleasant Prairie with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Pleasant Prairie?
In Pleasant Prairie, popular vacation rental amenities include kitchens, allowing guests to prepare their own meals, which is ideal for families or groups. Many rentals also feature decks or patios, providing outdoor spaces for relaxation and enjoying the surrounding nature. Fireplaces are commonly found in these properties, creating a cozy atmosphere during the colder months. Onsite parking is another convenient amenity, ensuring that guests have easy access to their vehicles. Additionally, air conditioning is often available, making stays comfortable during warm summer days.
When is the best time to visit Pleasant Prairie for a vacation rental?
The peak season for visiting Pleasant Prairie spans from May to July, with July being the most popular month for travelers seeking a delightful summer getaway. This vibrant time of year attracts families and outdoor enthusiasts eager to enjoy the beautiful parks, lakes, and recreational activities that the area offers. With temperatures typically ranging from the mid-60s to the low 80s Fahrenheit, visitors can comfortably explore local attractions, indulge in outdoor picnics, or partake in water activities on Lake Michigan.

During these summer months, you'll find a lively option with plenty of events and activities, making it an excellent choice for those seeking a fun-filled vacation. The warm weather invites visitors to take advantage of Pleasant Prairie's scenic trails and parks, superb for hiking, biking, or simply enjoying a leisurely stroll while taking in the picturesque surroundings.

For travelers looking for a more budget-friendly option, consider planning your visit in December. This month, while cooler with temperatures often in the low 30s Fahrenheit, offers a unique charm with holiday festivities and a quieter atmosphere. It's an excellent time for cozy indoor activities and exploring local shops.
How early should I book a Pleasant Prairie vacation rental?
Book your Pleasant Prairie vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Pleasant Prairie, Wisconsin, United States of America?
In Pleasant Prairie, visitors can enjoy a variety of attractions that cater to outdoor and recreational interests. The stunning Lake Andrea, located within the Prairie Springs Park, offers opportunities for fishing, paddle boating, and relaxing along the shore. The park features trails for walking and biking, making it a great spot for nature enthusiasts.

Additionally, the Pleasant Prairie Premium Outlets provide a shopping experience with a range of designer and brand-name stores, great for those looking to indulge in retail therapy. For family-friendly activities, the nearby RecPlex offers sports facilities, swimming pools, and fitness classes, providing fun options for all ages.

The area is also close to the vibrant city of Kenosha, where attractions like the Kenosha Public Museum and the Dinosaur Discovery Museum can be explored, adding more cultural and educational experiences to your visit.
Can I change or cancel my Pleasant Prairie home rental booking on Vrbo?
To find Pleasant Prairie vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Pleasant Prairie vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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