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.

5 out of 5 average rating, 19 reviews

Blue Sky Landing

Enjoy a stylish experience at this centrally-located studio.Walking distance to popular restaurants/ taverns, Downtown and Lake Michigan.Separate private entrance for all units. Kitchenette with microwave, airfryer and toaster plus fully stocked cabinets for everything you need to stay in and enjoy meals.Water cooler with hot/cold water and Keurig coffee maker with a selection of premium coffees and teas.Nice size bathroom with shower and jacuzzi bath. Salon quality Shampoo/Conditioner provided

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.

Superhost

Tiny home in Beach Park

4.84 out of 5 average rating, 104 reviews

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

Superhost

4.84 out of 5 average rating, 56 reviews

Bekahs Boho House

Make some memories at this unique and family-friendly place located in a beautiful neighborhood steps away from a park and baseball field. This location includes a private fenced in backyard, fire-pit, and grill for enjoying outside activities. Central location to grocery and retail stores. Private driveway and free street parking. Free wifi and Apple TV available. Per Airbnb policy we have outside surveillance cameras for safety purposes. No large parties allowed per Airbnb policy.

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!

4.95 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

Superhost

Flat in Waukegan

4.78 out of 5 average rating, 58 reviews

Cozy Apartment I Naval Station

AlexRating, 5 stars3 weeks ago

I stayed for about two weeks while I was working in the area. It was the prefect location, close to highways and grocery stores. I travel with my dog and she was allowed in the rental which was a huge help. We went on many walks around the neighborhood which is very nice and quiet. The kitchen is so nice I think that was a favorite part. Thank you!

4.73 out of 5 average rating, 40 reviews

Designer luxury loft in perfect downtown location

MariaRating, 5 stars1 week ago

Our stay was great! It aligned well with the description, the pictures and the reviews. A well appointed, digitally enabled modern space, a refreshing surprise in the heart of Kenosha.

4.94 out of 5 average rating, 271 reviews

Flat in Milwaukee

Cozy 1BR Close to Fiserv with Parking

MichelleRating, 5 stars3 days ago

The communication was proactive and clear. It was a great value compared to local costs. There are several dog residents you may encounter riding the elevator (w/ their owner of course). Everyone was friendly. Wish I had more time to use all the amenities.

Place to stay in Racine

4.86 out of 5 average rating, 722 reviews

Wisconsin Treehouse Getaway!

NancyRating, 5 stars1 day ago

Amazing cozy place! We spent our honeymoon here and there were lots of great restaurants to eat from. Close by the beach and had a lovely beach day. Check out my TikTok under nancyluzarroyo for more inside footage of the place!

4.78 out of 5 average rating, 194 reviews

Private room in Kenosha

Private Cozy Brm with Bathrm and nearby Lake View

CynthiaRating, 5 stars1 week ago

Carlton's room was peacful and quiet. Perfect for sleeping. It was also close to Lake Michigan, so I went over to the park nearby there to have my dinner at sunset.

5 out of 5 average rating, 9 reviews

Little House by the BIG LAKE

CorieRating, 5 starstoday

We travel a lot, and this was perhaps our best experience yet. Our daughter and son-in-law wanted to celebrate their first wedding anniversary in Kenosha and be close to the lake. We vacation here a lot. Our older son who lives in Chicago joined us. This space was perfect for 5 adults. Short walk to beach (though I prefer Simmons Island which is short drive north). Beautiful walking in this area. Since we had so many favorite spots to visit, I didn’t cook here. Too bad. I usually do, and this was the best-equipped kitchen I have rented. We visit beach often and so we brought everything we’d need for that. Ethan actually also had all of that in the closet, so I didn’t need to bring all of our stuff. Beautifully decorated home. Hosts have thought of everything. I had a unique request the day before we left. Host easy to reach and also accommodating in response. We would love to bring our 85+ parents here next year. Rent this place if you can!

4.85 out of 5 average rating, 40 reviews

Backyard Oasis- 5BDRM, Firepit, Safe Area, By Lake

PatriciaRating, 5 stars2 days ago

Such a beautiful and spacious house - my grandkids came by and really enjoyed the foosball and air hockey in the basement, and my musical brother and sister used the piano and guitars for us all. The kitchen was very well equipped with everything we needed. The neighborhood was quiet, and being a residential area, it was handy to have street parking as well as the driveway for our meal and game times. Downtown was just a couple of turns away, easy to get to. If I ever lure my whole family back to Kenosha, I will definitely rent this again. Thanks Leida!