Holiday rentals in Pleasant Prairie

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.

Spacious 2-BDRM/ Safe area Great for work & vacay

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.

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.

J’s Farmhouse Cottage. 2 bedroom duplex.

Formerly known as Magnolia Farmhouse inspired. 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, 45 miles from Chicago, and 2 miles from having your toes in the sand at Lake Michigan! We are minutes away from the Great Lakes Naval Station (9 mi) and the Cancer Treatment Center of America, Six Flags Great America, Gurnee Mills, and Great Wolf Lodge.

TheGlassCabin @ HackmatackRetreat

The Pond House, a vintage glass cabin filled with art, water views & eclectic vibes privately perched on the sacred grounds of Hackmatack Retreat Center. Native prairie, a winding slow river, two ponds, 200+ year old oaks & big sky- Countless places to curl up, gathering, focus-- nooks and crannies indoors and out, we offer “time out for time in” amidst this noisy world. Minutes from 2 small towns, all amenities, we're all about peace & ease-- let us custom curate your experience !

Cozy mother inlaw suite. Private. Next to beach.

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.

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!

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.

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!

Little House by the BIG LAKE

Only a few steps away from Lake Michigan, our well-appointed home is your southeast Wisconsin retreat. The home is in a peaceful, safe neighborhood, less than 2 blocks from the Eichelman scenic park/beach. Kenosha's downtown which is loaded with fun shops, restaurants, cafes and breweries is a short walk away. Take a stroll to the harbor, lighthouse, Civil War Museum, and marina. Great Lakes Naval Station is 1/2 hour down the lakefront.

Modern! Pro Cleaned, Self Check In - Sleeps 10

Enjoy your time together in this modern three bedroom one and a half bath ranch. The newly updated interior will make you feel like you have arrived. Stately hardwood floors accent the new decor. Kitchen is stocked for your inner gourmet cook. You will love all the stainless steel appliances. With our all new queen double plush beds, you will enjoy the ultimate sleep experience.

Kenosha Gateway Getaway

Experience a modern retreat in the heart of Kenosha! Conveniently located just minutes from three colleges, downtown hotspots, and within walking distance of the picturesque Lake Michigan shoreline. Whether you're visiting to relax or explore, our home is the perfect base for making the most of your time in Kenosha.