
Holiday rentals in Pleasant Prairie
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Top-rated holiday rentals in Pleasant Prairie
Guests agree: these stays are highly rated for location, cleanliness and more.

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

Nonsmoke, No Cleaning Fees, No Long Chore Lists.
25 minutes away from the Naval Station 5 minutes away from the beach. 10 minutes to Wisconsin. 1 hour 40 minutes to O’Hare Airport and downtown Chicago. 40 minutes to Milwaukee Airport 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 8PM.

Downtown-Treetop Deck-2Bd/2Bth
Discover this one-of-a-kind, shabby-chic second-floor apartment in the heart of Downtown Kenosha — just steps from coffee shops, restaurants, museums, and the shores of Lake Michigan. Ideal for travelers who want everything within walking distance. Relax and unwind on the spacious, completely private back deck — your own hidden oasis tucked among treetops and historic neighborhood buildings. Perfect for stays up to four guests. Please note: This property is not suitable for young children.

Bay View MKE Hideaway - with Parking!
Cozy, inviting, one bedroom apartment in the heart of Bayview, literally steps away from some of Milwaukee's best restaurants, bars and shops! One of two Airbnb guest spaces in our house, this downstairs apartment is our home base when we're in Milwaukee, and we love sharing it with guests when we’re on the road! We are within five minutes of Summerfest grounds and East Side & Historic Third Ward districts, and within 10 minutes of the airport, downtown, Marquette University, and Miller Park.

Exquisite Modern A-frame all WithInnReach
An amazing space that truly caters to the guest experience. We've built this art piece to have our guests immerse themselves in all the amenities, from heated floors to in-ceiling speakers - all whilst losing yourself in the wood burning fireplace. At WithInnReach the attention to detail was paramount - with an emphasis of what we enjoy...amazing food through a well balanced kitchen, beautiful sound through Klipsch speakers and relaxation with floor to ceiling showers...enjoy to the fullest.

Master qtr close to nature & easy urban facilities
This amazing prairie style home sits on 2 acre land surrounded by lush lawn and majestic oak trees - a nature lover's dream with unparalleled serenity. Vacation-like setting blends country-like quiet with nearby conveniences including shopping, trains, restaurants, highways, Ravinia (18 MINs drive). 5 MINs to I 294. 20 MINS to O'HARE; 5 Mins to Discover, Baxter; 10 MINs to Walgreens Deerfield campus, TRINITY INT'L UNIVERSITY; 15 MINS to Lake Forest Academy. 25 MINs to Great Lakes Navy Base.

Funky 2BR in Prime Bay View - w/ Parking
Perfectly located on the main strip of KK in MKE's eclectic Bay View directly next to restaurants and bars. Minutes from downtown, Summerfest, art museum. You’ll have the entire first floor of this sunny duplex. Stylishly designed - 2 bedrooms with Casper mattresses, a bright kitchen with seating area, record player, a work space in the master, and a comfy living room with a smart TV. The space has a small backyard area, an in-unit washer & dryer as well as 1 off-street parking space.

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!

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!

Charming log cabin in the woods
This log cabin is an old hunting lodge. It is rustic, charming and quaint, nestled in the woods of Wisconsin and next to a tranquil pond. The location is close to the Johnson Park golf course and 5 miles from the beautiful Lake Michigan shore. It is a perfect place to relax, write or escape from the stress of life. In the winter a 4-wheel drive vehicle is necessary to reach the site. Please note: bathroom facilities are a close walk away. Heating from wood stove only.

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.

Calm here! Cozy, spacious, comfortable, lg space
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.
Popular amenities for Pleasant Prairie holiday rentals
Other great holiday rentals in Pleasant Prairie

Beach House Retreat with Firepit and Game Room

Designer luxury loft in perfect downtown location

Lago Amore - Channel house, pier, kayaks

Spacious Family Friendly Cottage, Close to Lake MI

Little House by the BIG LAKE

Lighthouse Retreat

Mid-Century Modern Dream Getaway

Wisc Winter Getaway-5BDRM, Firepit, Near the Lake
When is the best time to visit Pleasant Prairie?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 92 | € 92 | € 92 | € 94 | € 110 | € 113 | € 124 | € 122 | € 103 | € 91 | € 102 | € 94 |
| Avg. temp | -4°C | -3°C | 3°C | 8°C | 14°C | 20°C | 23°C | 22°C | 18°C | 12°C | 5°C | -1°C |
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 10 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 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 10 homes with a kitchen, over 10 homes with free parking, over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.
Quick stats about holiday rentals in Pleasant Prairie

Total holiday rentals
Explore 30 holiday rentals in Pleasant Prairie

Nightly prices starting at
Pleasant Prairie holiday rentals start at € 43 per night before taxes and fees

Verified guest reviews
Over 1,900 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space & child-friendly amenities

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Pleasant Prairie holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Pleasant Prairie rentals

4.9 Average rating
Pleasant Prairie stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Alpine Valley Resort
- Oak Street Beach
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Wilmot Mountain Ski Resort
- Milwaukee County Zoo
- The 606
- Racine North Beach
- Chicago Cultural Center
- Richard Bong State Recreation Area
- Bradford Beach




