Vacation rentals in Pleasant Prairie

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Top-rated vacation rentals in Pleasant Prairie

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Guest favorite

Home in Kenosha

5.0 out of 5 average rating, 26 reviews

Sister House Cottage-Beachy Charm-Driveway Parking

Sister House Cottage is a 1920’s bungalow charmingly furnished in a beachy vintage theme. A restful screened in front porch looks out onto a quiet tree filled, family oriented neighborhood. Enjoy the many lovely beaches in Kenosha with provided beach towels, lawn chairs and sand toys! Just a 5 minute drive to Lake Michigan! 3 blocks from large park with playground, disc golf and garden. To help make your family stay more relaxing we offer a portable crib, stroller and high-chair for your use.

Aug 18 – 25

ﺩ.ﺇ542 per night

Guest favorite

Condo in Kenosha

4.93 out of 5 average rating, 172 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.

Sep 14 – 21

ﺩ.ﺇ316 per night

Guest favorite

Apartment in Kenosha

4.92 out of 5 average rating, 213 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.

Aug 15 – 22

ﺩ.ﺇ354 per night

Guest favorite

Home in Beach Park

4.98 out of 5 average rating, 161 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.

Jan 28 – Feb 4

ﺩ.ﺇ480 per night

Guest favorite

Apartment in Kenosha

4.98 out of 5 average rating, 217 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!

Dec 5 – 12

ﺩ.ﺇ464 per night

Superhost

Apartment in Kenosha

4.92 out of 5 average rating, 12 reviews

Designer luxury loft in perfect downtown location

Escape to our spacious and luxurious designer open-space loft with panoramic downtown views through our giant windows. Whip up your favorite meals in our modern kitchen with modern stainless-steel appliances and plenty of storage space. A cozy and comfortable bed, smokeless fireplace, and ample walk-in closet ensure a clutter-free and restful environment. Treat yourself to a rain shower in any of the two bathrooms, complete with luxurious features like towel and mirror warmers.

May 9 – 16

ﺩ.ﺇ575 per night

Guest favorite

Guest suite in Zion

4.89 out of 5 average rating, 138 reviews

Non-smoking, attached mother-in-law suite.

30 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour to O’Hare Airport and downtown Chicago. 1 hour to Milwaukee 25 minutes to Six Flags and Great Wolf Lodge. Safe and quiet neighborhood with plenty of wildlife right in the back yard. This Mother in Law suite has tons of natural light. For nature lover’s this unit is close to the beach and there are walking trails nearby. Small children maybe heard from 7AM to 7PM.

May 2 – 9

ﺩ.ﺇ297 per night

Guest favorite

Home in Kenosha

4.97 out of 5 average rating, 197 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.

Sep 25 – Oct 2

ﺩ.ﺇ456 per night

Superhost

Home in Racine

4.89 out of 5 average rating, 355 reviews

The July House - lake views - 3B/1 amazing bath

You won't want to pass up amazing lake views from this charming house! This place is designed for guests, including a newly renovated bathroom upstairs that will rival any upscale hotel AND a brand new bath in the lower basement level. Lake view from living/sitting room and all bedrooms. Walking distance to downtown food/shops. Beds: king, queen, full, twin with twin trundle. Available if needed: 2 pack-n-plays and full size air mattress.

Dec 1 – 8

ﺩ.ﺇ455 per night

Guest favorite

Apartment in Winthrop Harbor

4.94 out of 5 average rating, 226 reviews

Love my guests! Homey Elegant & Lake Michigan!

Large, Cozy, suite w sweet kitchenette for “portable” meals; full-size refrigerator/ freezer; a writing desk for work. Many little ( in case you forgot) items to keep you comfy. This is a quiet town on the gorgeous Lake Michigan. Near: 6 Flags, Great Lakes Navy Base; Cancer Treatment Centers of America & the city Chicago via the Metra in town. Convenient & Quiet. I have 3 dogs. They are kind, outgoing and will want to meet you.

Sep 22 – 29

ﺩ.ﺇ321 per night

Guest favorite

Apartment in Kenosha

4.98 out of 5 average rating, 114 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.

Nov 5 – 12

ﺩ.ﺇ435 per night

Guest favorite

Cabin in Kenosha

4.81 out of 5 average rating, 534 reviews

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! Fully remodeled. Perfect for ice fishing in the winter. A Sportsman’s paradise. Ideal for the adventurous. Relax, do some writing or work overlooking the breathtaking scenery. A stone's throw to the beach. Massive deck overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Oct 21 – 28

ﺩ.ﺇ428 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pleasant Prairie vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pleasant Prairie's top sights

Bristol Renaissance Faire35 locals recommend

Pleasant Prairie Premium Outlets59 locals recommend

Cheddar's Scratch Kitchen3 locals recommend

Brat Stop3 locals recommend

Jelly Belly Center16 locals recommend

The Spot Drive-In17 locals recommend

Other great vacation rentals in Pleasant Prairie

Guest favorite

Home in Kenosha

5.0 out of 5 average rating, 52 reviews

Tu Casa Cottage - Your Home Away From Home

Jul 13 – 20

ﺩ.ﺇ378 per night

Guest favorite

Apartment in Kenosha

5.0 out of 5 average rating, 18 reviews

Anna's Cozy One Bedroom Lakefront Apartment

Dec 9 – 16

ﺩ.ﺇ568 per night

Guest favorite

Guest suite in Union Grove

4.97 out of 5 average rating, 76 reviews

Peaceful Horse Farm Retreat

Jan 3 – 10

ﺩ.ﺇ564 per night

Guest favorite

Home in Kenosha

5.0 out of 5 average rating, 96 reviews

LITTLE HOUSE by the BIG LAKE

May 21 – 28

ﺩ.ﺇ744 per night

Guest favorite

Home in Pleasant Prairie

5.0 out of 5 average rating, 13 reviews

Large Modern Lake Michigan Beach House & Game Room

Jul 9 – 16

ﺩ.ﺇ1,416 per night

Guest favorite

Home in Antioch

4.96 out of 5 average rating, 26 reviews

Hideaway Lakehouse

May 7 – 14

ﺩ.ﺇ519 per night

Guest favorite

Cottage in Racine

4.99 out of 5 average rating, 76 reviews

Clementine Cottage

Sep 19 – 26

ﺩ.ﺇ614 per night

Guest favorite

Condo in Racine

4.91 out of 5 average rating, 35 reviews

Artist loft in Racine

Jun 12 – 19

ﺩ.ﺇ386 per night

Show all

Quick stats about vacation rentals in Pleasant Prairie

Total rentals
30 properties
Wifi availability
30 properties include access to wifi
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Family-friendly rentals
20 properties are a good fit for families
Total number of reviews
1.5K reviews
Nightly prices starting at
ﺩ.ﺇ184 before taxes and fees

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 $50 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 20 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 10 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 wifi, over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Pleasant Prairie

Top-rated vacation rentals in Pleasant Prairie

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Pleasant Prairie vacation rentals

Stay near Pleasant Prairie's top sights

Other great vacation rentals in Pleasant Prairie

Home in Kenosha

Apartment in Kenosha

Guest suite in Union Grove

Home in Kenosha

Home in Pleasant Prairie

Home in Antioch

Cottage in Racine

Condo in Racine

Quick stats about vacation rentals in Pleasant Prairie

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in house rentals in Pleasant Prairie?

Are there vacation rentals with a dedicated workspace in Pleasant Prairie?

Do house rentals in Pleasant Prairie have air conditioning?

Do house rentals in Pleasant Prairie have wifi?

Are there family-friendly vacation rentals in Pleasant Prairie?

Do house rentals in Pleasant Prairie have a kitchen?

Do house rentals in Pleasant Prairie have free parking?

What are the most popular amenities for House Rentals in Pleasant Prairie?

Destinations to explore