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Vacation rentals in Pleasant Prairie

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Top-rated vacation rentals in Pleasant Prairie

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Rental unit in Kenosha

4.92 out of 5 average rating, 234 reviews

Cheerful Apartment in Downtown Arts District

Cheerful apartment in newly renovated building above Professional Acting Studio at edge of Kenosha's Downtown Arts District. Near Harbor, beach, 4 museums, art galleries, live entertainment, eclectic restaurants, diners, coffee shops, Trolly, bike paths, parks, lakeshore, antique stores and specialty shops, Prime Outlets, Bristol Renaissance Faire, Great America. Metra Line to Chicago, close to Milwaukee. My place is good for couples, solo adventurers, business travelers, friends and families.

Condo in Kenosha

4.92 out of 5 average rating, 207 reviews

Inviting, spacious apt! Ideal for stay & work

This brand new basement apartment is an amazingly pleasant, spacious and private unit (over 950 sq. ft). Whatever the motive of your trip is —work from home, business, family function, wedding, graduation, friends, or simply a vacation escapade — you will enjoy the freedom this space provides. This residential, private neighborhood apartment is carefully designed. The full kitchen, classy bathroom, plush and extra-comfortable king size bed, the TV and all the amenities will fulfill your needs.

Home in Beach Park

4.97 out of 5 average rating, 192 reviews

B’s Farmhouse Cottage 2-bedroom duplex.

Experience the best of the midwest! Enjoy a newly remodeled "Magnolia Farm" inspired 2-bedroom duplex, all to yourself near everything you need. 50 Miles from Milwaukee, miles from Chicago, and 2 miles having your toes in the sand at Lake Michigan. We are minutes away from the Great Lakes Naval Station and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge. Whatever brings you here make J&B's Farmhouse Cottage your home away from home today.

Home in Kenosha

5 out of 5 average rating, 125 reviews

LITTLE HOUSE by the BIG LAKE

Only steps away from Lake Michigan, our well-appointed home is your southeast Wisconsin retreat. The home is in a peaceful, safe neighborhood, less than 2 blocks from the Eichelman scenic park/beach. Kenosha's downtown which is loaded with fun shops, restaurants, cafes and breweries is a short walk away. Take a stroll to the harbor, lighthouse, Civil War Museum, and marina. Great Lakes Naval Station is 1/2 hour down the lakefront. Dates not available? Check out The Cozy Cottage next door.

Guesthouse in Lake Forest

4.95 out of 5 average rating, 115 reviews

The Green Door - safe and calm with walkability

This charming guesthouse in Lake Forest is only steps away from beautiful Market Square — the historic retail center of the community. Inside it features loads of light, in-unit washer and dryer, a well-equipped kitchen and a professionally designed stylish and calming interior. Outside, it has a vintage (ie. older) porch/breezeway with classic outdoor games. Walk to two grocery stores, bars/restaurants and our historic train station that connects to Chicago and various corporate shuttles.

Home in Kenosha

4.92 out of 5 average rating, 260 reviews

A Home for your Holiday! Hot tub/Chefs Kitchen

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

Villa in Racine

4.96 out of 5 average rating, 116 reviews

Gorgeous historical mansion on Lake Michigan

Welcome to the historic Carpenter House! This is an opportunity to stay in a former Bed & Breakfast overlooking Lake Michigan. A historical neo-classical home built in 1896 with tons on history. The home was completely renovated a few years ago. Wake up and sit on the front porch and enjoy the beautiful view of Lake Michigan. The house is located in the historical district in Racine. The home boasts a ballroom on the 3rd floor that is suitable for small events and a private cute garden.

Rental unit in Kenosha

4.98 out of 5 average rating, 227 reviews

Kenosha! Enjoy your stay as you work or play!

Soft towels, fluffy pillows, complimentary breakfast, soft drinks, and more in a safe and secure environment. Only children over 13 allowed and must be accompanied by an adult. This n-smoking, pet-free 1-bedroom w/king bed, twin mattress daybed and cot, furnished kitchen and bath apartment is on the 2nd floor of an office building. Free HI-SPD Wi-Fi and big screen Smart TV. Access to museums, universities, shopping, Chicago’s METRO train and only 37 miles from downtown Milwaukee!

Home in Round Lake Beach

4.99 out of 5 average rating, 121 reviews

Round Lake Getaway Retreat

Looking for a calming, peaceful lakeside getaway for you and your loved one? Come stay at our remodeled retreat with private waterfront access to Round Lake. Enjoy peace and reflection meditating on the spirited lake waters rolling into shore. Wake up to inspirational lake views with soul warming coffee, tea or cocoa. Savor deep or lazy conversation with your loved one, surrounded by dreamy décor and captivating nature. Come and relax, restore, and rejuvenate by the lake!

Home in Kenosha

4.96 out of 5 average rating, 217 reviews

Lovely home near the beach in a safe neighborhood

Our simple, yet welcoming property is minutes away from beaches, downtown, minor league baseball, the farmers market, and many delicious restaurants, as well as having close proximity to Carthage College, 6 Flags, and a quiet 30 min drive to Great Lakes Naval Base. We are located in the Allendale neighborhood boasting a family-friendly atmosphere on a quiet street. Whether you are here to relax, have fun, or attend special events, our house can provide.

Rental unit in Kenosha

4.99 out of 5 average rating, 148 reviews

Downtown-Treetop Deck-2Bd/2Bth

This one-of-a-kind, shabby-chic second floor apartment is in the heart of Downtown Kenosha, walking distance to coffee shops, restaurants, museums, and Lake Michigan beaches. Enjoy the large, completely secluded back deck equipped to grill, dine, and relax tucked amongst neighborhood buildings with a tree top view. The apartment is great for a romantic rendezvous, a girlfriend getaway, or for an extended stay.

Condo in Racine

4.97 out of 5 average rating, 240 reviews

Gorgeous renovated 1200sf apt with lake views

Beautiful completely renovated and modernized 1,200 sq. ft 1 bedroom apartment on the upper floor of an old Main Street commercial building from the late 1800s in Racine. In addition to all the modern amenities inside the apartment, you'll enjoy using the "attached" public parking garage ($3.50), which allows you to enter a few short steps from where you park - without climbing any stairs at all.

Vacation rentals for every style

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Popular amenities for Pleasant Prairie vacation rentals

Free parking on premises

Air conditioning

Stay near Pleasant Prairie's top sights

Pleasant Prairie Premium Outlets59 locals recommend

Bristol Renaissance Faire35 locals recommend

Franks Diner24 locals recommend

The Spot Drive-In17 locals recommend

Jelly Belly Center16 locals recommend

Kenosha Kingfish Baseball Club10 locals recommend

Other great vacation rentals in Pleasant Prairie

Home in Winthrop Harbor

5 out of 5 average rating, 15 reviews

Harbor Haven/Near Base/Great America/Game Room/Gym

Condo in Racine

4.94 out of 5 average rating, 66 reviews

Artist loft in Racine

Home in Kenosha

4.97 out of 5 average rating, 38 reviews

Waterfront w/Lake Views, walk to the beach!

Home in Kenosha

5 out of 5 average rating, 24 reviews

Spectacular Lake Michigan views

Home in Racine

4.95 out of 5 average rating, 21 reviews

Mid-Century Modern Dream Getaway

Townhouse in Kenosha

5 out of 5 average rating, 13 reviews

Lakeside Song

Home in Antioch

4.98 out of 5 average rating, 41 reviews

Hideaway Lakehouse

Home in Waukegan

5 out of 5 average rating, 12 reviews

Cozy Vacation retreat

Quick stats about vacation rentals in Pleasant Prairie

Total rentals
30 properties
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees
Total number of reviews
1.7K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wifi availability
30 properties include access to wifi

Frequently Asked Questions

How much does it cost to stay in house rentals in Pleasant Prairie?
Experience the best of Pleasant Prairie with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Pleasant Prairie?
Yes! Work meets play with ease at over 20 vacation rentals in Pleasant Prairie featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Pleasant Prairie have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Pleasant Prairie. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pleasant Prairie have wifi?
Absolutely! We offer over 20 house rentals with wifi in Pleasant Prairie. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Pleasant Prairie?
Pleasant Prairie has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Pleasant Prairie have a kitchen?
Absolutely! We offer over 20 house rentals with a kitchen in Pleasant Prairie. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Pleasant Prairie have free parking?
Absolutely! We offer over 10 house rentals with free parking in Pleasant Prairie. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Pleasant Prairie?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a kitchen, over 20 homes with wifi, over 10 homes with air conditioning, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore