Vacation rentals in Pleasant Prairie

Spacious 2 BRM- Perfect for Work or Getaway

You will enjoy this carefully designed, well-decorated and well-furnished basement apartment. It is roomy (over 950 feet), pleasant, private and quiet in a residential area. Whether you ( 1-4 guests) come for work, business, family or a special function, its full kitchen, classy bathroom, extra-comfortable king and queen size beds, blender, high-speed internet and ergonomic chairs (2nd on demand) as well as free parking will add comfort and extra ease to your stay, and make it one to remember.

Unique Dome Home Golf Range Experience by the Lake

As featured in Golf Digest, this memorable place is anything but ordinary! Our spacious dome home is perfect for a quiet weekend away or hosting a large group of people. Located on a secluded driving range with your own private access and 1 mile west of Lake Michigan, our location is perfect! Beaches, parks and two golf courses all within 10 miles from the house! Here in the winter? No problem! We have ski hills all around us! Our home is the perfect place to resort to after a day on the slopes.

Bekahs Boho House

Make some memories at this unique family-friendly place located in a beautiful neighborhood steps away from Becker park. This location includes a private fenced in backyard, covered porch, fire-pit, and grill for enjoying outside activities. Central location to stores and 15 min from Renaissance fair! 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.

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.

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.

Wisconsin Treehouse Getaway!

Featured in Timeout Magazine as Chicago's Top 10 Airbnbs, and in other outlets as Wisconsin's most romantic and top 5 Airbnbs, this space has an immersive nature experience, overlooking a creek and woods with all modern comforts. Imagine yourself in a cabin in the woods to unplug and recharge, waking up to chirping birds as if in a Treehouse! 3 miles to Lake Michigan & dwntn. lf we're home, a complimentary Chai! Come, make lifelong memories at Racine's Best Kept Secret No local bookings.

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.

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.

Kenosha Retreat - Created to help you Relax

Relax with the whole family in this peaceful home, created with real intention to help you slow down and enjoy being together. It’s an easy, comfortable space that feels calm the moment you walk in. You’re close to everything—bike to the lake, walk to the Kenosha Kingfish baseball park, or take a quick drive downtown or to the highway. The neighborhood is friendly, parking is easy, and everything about your stay is meant to feel simple and relaxing.

6th Ave Harborside

Perfectly located near downtown Kenosha, this cozy and comfortable home makes it easy to enjoy the best of the area. Ride the bikes to the farmers market, stroll to the beach, or spend time along the marina and harbor. The large dining room invites long meals and relaxed evenings together. An ideal home base for a peaceful getaway, visiting family, or attending local events. One night stays are available on a limited basis - reach out for details!

Lake Michigan Writer’s Cabin

Beautiful Lake Michigan retreat perfect for relaxing, boating, fishing, swimming and more! A true cabin experience. 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. Two decks overlooking the tranquil landscape. A short walk to downtown shops, cafes and restaurants.

Lighthouse Retreat

Discover a unique lakeside-style retreat in the heart of Kenosha! Perfectly situated just minutes from three colleges, downtown attractions, and within walking distance of the stunning Lake Michigan shoreline. Whether you're here to explore or unwind, our home offers the ideal base to enjoy all that Kenosha has to offer!