
House vacation rentals in Pleasant Prairie
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Top-rated house rentals in Pleasant Prairie
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Center Lake View Cottage, near Camp&Silver Lakes
Relax & enjoy your stay in this peaceful home in quiet, friendly neighborhood. Launch your boat in Center Lake at end of street or visit one of many lakes nearby. Camp Lake less than 2 minutes away, close to Silver Lake and others. This home has an awesome sled hill, fire pit with seating area, and a relaxing deck with lake views. Close to Wilmot Mountain, Lake Geneva, & Bristol Renaissance Faire. 25 mins to Six Flags or Lake Geneva, 1 hr to Chgo or Milwaukee. 35 mins to Great Lakes Naval Base

Bright, Airy SuperHost’s Kenosha Backyard Home
Newer, modern 4BR/2.5BA home in peaceful residential neighborhood. 10min from beautiful Kenosha beaches, Microsoft, UWP, Carthage, harbor market, museums, restaurants, & more! The house features 2 dining areas, dedicated office space, and a large unfenced backyard with relaxing patio seating. Very family friendly! Perfect for your family vacation, friends getaway or business trip -we are experienced hosts. Book with confidence! 30min to Milwaukee airport, 50min to O’Hare, 25min to Six Flags

Stunning Home Across The Street From North Beach
Newly remodeled home on Michigan Blvd. We went the extra mile in creating this beautifully curated, lush, and stylish home! Kick back and relax in one of the many thoughtfully designed rooms and the huge front outdoor deck with amazing views of Lake Michigan! Anywhere you gaze, you will find a visually stimulating experience in this home! Across the street from Lake Michigan, North Beach, and Kids Cove Playground. Short walk to Racine Zoo, the Marina, downtown Racine shops and restaurants.

Beautifully Restored Historic Victorian
Whether this is for a single, couple, or small group, your stay at this historic home will truly be memorable. You’ll love the MBR suite featuring a gas fireplace, whirlpool tub, and double walk-in custom tile shower. There is an additional very nice full bath/shower on the main floor. The finished lower level has two separate rooms, each with a quality double futon with bedding available for your guests. For this attractive price, the upper 4 bedrooms are locked but may be opened for more

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.

Hot tub getaway close to Lake Michigan beaches
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.

Victorian! Pro Cleaned, Self Check In - Sleeps 10
This Victorian style "Homes by Christopher" has been completely renovated. New comfy plush beds with extra lumbar support and Serta Cool Gel pillows. You will get lost in history as you gaze at the stylish artwork throughout the home. It has blazing fast WiFi internet with U-Verse TV. The smart TVs have Roku, Netflix, and more with thousands of channels to choose from. The furnishings are themed to add to its ambiance. We have spared no expense in making it super nice for you! Book now!

Lakefront, beautiful views, spacious and private.
With panoramic views of the lake, you’ll love the stunning sunsets, private beach, pier, and kayaks. Experience outstanding fishing and walk to downtown for restaurants, bars, shopping, theater, and concerts in the park. Skiing at Wilmot/Vail is just a short drive away. Inside, unwind by two fireplaces, three TV screens, or play a game on the pool table. The large wet bar and expansive kitchen are perfect for gatherings, with additional space in the dining areas, private office, and gym.

Lakeside Getaway
Relax with the whole family at this peaceful, home on Lake Beulah. With the gorgeous lake and surrounding nature, you will feel you are hours up North, minus the long commute! Wake up and enjoy coffee on the deck. Bring your boat or grab a floaty and soak up the sun as you spend the day on the water. Wind down while you watch a stunning sunset from your own pier. Enjoy a show at the nearby Alpine Valley. Countless memories are just waiting to be made. Come play hard and relax even harder

Charming Lake Geneva, Wisconsin 3BR/2Bath Home
Step into the comfort of this sun-soaked 3BR 2Bath home in a tranquil area in Lake Geneva, WI. This relaxing retreat with a picturesque private pond is immersed in a breathtaking natural ambiance offering a perfect escape from the big city crowds. The stylish design and rich amenity list will leave you in awe. ✔ 3 Comfortable Bedrooms ✔ 2 Living Areas ✔ Sunroom ✔ Fully Equipped Kitchen ✔ Patio with a grill ✔ Pond Access ✔ High-Speed Wi-Fi ✔ Smart TVs ✔ Board Games/ Learn more below!

TheGlassCabin @ HackmatackRetreat
The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Lake Michigan Paradise Apartment
Private, top floor unit in a duplex on Lake Michigan w/ 900 square feet, 2 bedrooms, 1 large bathroom with shower and soaker tub, open concept living perfect for an amazing getaway. Unobstructed views of Lake Michigan. Relax on your enormous 500 square foot private deck overlooking the lake. Great for fishing. Backyard available for your furry family members. Beach is around the corner. Downtown is a 3 minute walk and has beautiful boutiques, shops, eateries, museums and more!
Popular amenities for Pleasant Prairie house rentals
House rentals with a pool

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Great girlfriend getaway with jacuzzi tub

Lake Geneva Home w/ Pool near the Lake!

Highwood Haven/Indoor Pool/Hot Tub/Arcade

Paradiso Vacation

Relaxing Getaway & Fall Fun near Lake Geneva

In Ground Pool, Full Ranch Home

Farmhouse with Heated Pool on almost 160 Acres!
Weekly house rentals

Lakefront 2BR | Deck | Fire Pit | Dog Friendly

Nancy's Place

Waterfront w/Lake Views, walk to the beach!

Lago Amore - Channel house, pier, kayaks

Lighthouse Retreat

Bekahs Boho House

Mid-Century Modern Dream Getaway

The Harbor House - Amazing!
Private house rentals

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

Relaxing Lakefront Stay w/ Deck and great views

Family Fun Zone! Theater, Arcade, Park Access

Cozy Lakehouse Only 20 min to Lake Geneva Area

Lakeside Getaway 1 Bedroom

Spectacular Lake Michigan views

Spacious Family Friendly Cottage, Close to Lake MI

Little House by the BIG LAKE
Quick stats about house rentals in Pleasant Prairie
Total rentals
10 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
10 properties are a good fit for families
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
10 properties include access to wifi
Destinations to explore
- Chicago Vacation rentals
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- Wisconsin River Vacation rentals
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Frank Lloyd Wright Home and Studio
- Alpine Valley Resort
- Oak Street Beach
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Geneva National Resort & Club
- Illinois Beach State Park
- Willis Tower
- Milwaukee County Zoo
- The 606
- Racine North Beach
- Grand Geneva Resort & Spa
- Wilmot Mountain Ski Resort
- Richard Bong State Recreation Area