Holiday rentals in Pleasant Prairie

4.98 out of 5 average rating, 103 reviews

Bright, Airy Keno-Microsoft, Carthage, UW-P 10 min

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

4.93 out of 5 average rating, 248 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.

4.98 out of 5 average rating, 224 reviews

Home in Beach Park

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.

4.89 out of 5 average rating, 200 reviews

Guest suite in Zion

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

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 7PM.

4.98 out of 5 average rating, 134 reviews

Cabin in Salem

A Frame Log Cabin Near Multiple Local Lakes

Experience the allure of Salem Lakes Chalet, featuring modern comforts nestled within a quaint 3-story log cabin. Relax in a fenced yard offering picturesque vistas of woods, and relish in the variety of recreational options at nearby lakes. Your ideal retreat beckons! Enjoy the northern ambiance without the lengthy journey—be amazed by our expansive wall of windows! Whether you are in town to visit family or looking for a retrieve from the city we are conveniently located 10 mins from I-94.

4.84 out of 5 average rating, 104 reviews

Tiny home in Beach Park

Tiny home in not so tiny Yard

The house has a Queen bed, a Single bed and a sofa. A tiny home in a peaceful neighborhood. Built on 4 city lots, it has plenty of space and privacy. For families visiting the Naval Academy, we are close enough, yet give you space and privacy. Away from the hustle of North Chicago and Waukegan. Nearby attractions are: Naval Base - 11 miles, 20 minutes Six Flags - 7 miles, 15 minutes Illinois State Beach - 2 miles, 5 minutes Chicago - 46 miles, 60 minutes Milwaukee - 50 miles, 55 minutes

4.82 out of 5 average rating, 136 reviews

Flat in Waukegan

Cozy Corner, stylish 1bed near Navy Base!

Kick back and relax in this calm, stylish space. This is a newly remodeled 1 bedroom apartment. The Cozy Corner is designed to be a place of peace, for rest and relaxation. Feel right at home in this beautiful apartment. The kitchen is stocked with plenty of utensils and cookware for your favorite meal. Be sure to relax by the indoor fireplace and watch your favorite movies. Dedicated work space with desk and fast wifi perfect for traveling professionals. Longer stays discounted!

4.98 out of 5 average rating, 235 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!

4.99 out of 5 average rating, 151 reviews

Home in Round Lake Beach

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!

4.89 out of 5 average rating, 199 reviews

Flat in Racine

The Graduate Apt Downtown

Experience downtown charm at our fully renovated Graduate Apt, a stone's throw from the lake. Enjoy serene views from Main St facing windows. Our apartment features a quiet bedroom with a queen bed and smart TV, and a cozy living room that includes a convertible queen sofa with premium linens. Indulge in a fully equipped kitchen, in-unit laundry, and complimentary Hulu access. Ideal for both business and leisure. Ask about our adjacent Greyhound Suite for larger groups!

4.95 out of 5 average rating, 243 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.

4.99 out of 5 average rating, 174 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.

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Other great holiday rentals in Pleasant Prairie

5 out of 5 average rating, 53 reviews

Home in Pleasant Prairie

Lakehouse Retreat with Game Room

GenieRating, 5 stars2 weeks ago

Beautiful house! Well maintained, clean, and very nicely decorated. The space is layed out nicely, and offers thoughtful amenities. I love that everything is labeled, including the light switches, so you know exactly where to get what. House is within walking distance of the beach. Cristina is very responsive and helpful with whatever we needed. We hope to stay here again soon!

4.89 out of 5 average rating, 38 reviews

Townhouse in Kenosha

Welcome to Lakeview Kenosha!

ReneaRating, 5 stars1 week ago

Great place with a beach at your front door! Scott thought of everything, all the comforts of home away from home. Very clean, comfortable beds and even a baby gate!

5 out of 5 average rating, 40 reviews

Nancy's Place

Mary KayRating, 5 stars1 day ago

Joe was an outstanding host, and we enjoyed staying in his home. Nancy's Place was clean, free of clutter, yet we loved all the little local and family art he had throughout the home. He responded very quickly to questions before our trip and was accommodating with our flight schedule with check-in and check-out. We will stay here the next time we are in town visiting 😀 Thank you,Joe!

4.98 out of 5 average rating, 54 reviews

Screened in Porch-7 min to Lake-Beautiful Decor

JillRating, 5 stars1 week ago

We stayed in Heide's place while visiting family in the area, and we couldn't have had a more wonderful experience. Everything was even better than the photos and better than described - so many delightful details (from the coffee pods in the kitchen to the stash of travel size toiletries in the bathroom to the basket of beach essentials in the closet) - no stone was left unturned. The neighborhood was quiet and friendly and central to anything you wanted to do in Kenosha or the surrounding area. The beds were comfortable (although it does get a little toastier in the upstairs loft than it does in the rest of the house, the A/C worked fine and it was very comfortable even on the hottest days.) We wouldn't hesitate to return to Heide's Beach Cottage or recommend it to others.

4.94 out of 5 average rating, 18 reviews

Lighthouse Retreat

AnnaRating, 5 stars1 week ago

Keith was such a welcoming and responsive host, we loved our stay at this lovely place. We felt right at home!

4.84 out of 5 average rating, 56 reviews

Bekahs Boho House

MichaelRating, 5 stars3 days ago

Great instructions, very comfortable and clean and had everything we needed and more.

4.69 out of 5 average rating, 72 reviews

Home in Zion

Secluded Retreat with Workspaces & Nature Trails

DenisRating, 5 stars1 week ago

Thank you for hospitality, it’s very clean, cozy and comfortable house. I’m recommend everyone this place 👍👍