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.

Guest favourite

Bungalow in Lake Geneva

4.97 out of 5 average rating, 138 reviews

Private Cozy Cottage Lake Geneva, WI

Come stay at our top rated Bed & Breakfast, located two blocks from the beautiful Lake Geneva. Relax in our California king suites, each contains a spa tub and shower, with heated floors and towel rails in the bathroom. Your complimentary breakfast basket is placed in your fridge prior to arrival, as well as complimentary gift of wine & cheese. Free WIFI is available on the property. No Pets, ADULTS over 21 ONLY. *NOTE all guests are required to pay a 8% Lake Geneva Bed Tax at check in.

Superhost

Home in Kenosha

4.92 out of 5 average rating, 265 reviews

Where Family & Friends Gather to Create & Remember

Come gather, relax & celebrate at our 1 acre estate near beaches, dining & Carthage College! The designer interior features 5 BR/4 Bath, chef's kitchen with Viking & Subzero, Coffee/Espresso Bar, dining area for 12, 2 spacious family rooms with piano, fireplace and TVs. Enjoy dining, lounging & fun in the great outdoors w/hot tub, fire pit, basketball, pickleball, ping pong & lawn games! Beaches are walkable under a mile & near lively downtown w/ harbor, restaurants, shopping & museums.

Guest favourite

Home in Antioch

4.9 out of 5 average rating, 127 reviews

Lakefront, beautiful views, spacious and private.

With panoramic views of the lake, you’ll love the stunning sunsets, private beach, pier, and kayaks. Experience outstanding fishing and walk to downtown for restaurants, bars, shopping, theater, and concerts in the park. Skiing at Wilmot/Vail is just a short drive away. Inside, unwind by two fireplaces, three TV screens, or play a game on the pool table. The large wet bar and expansive kitchen are perfect for gatherings, with additional space in the dining areas, private office, and gym.

Guest favourite

Home in Lake Geneva

4.94 out of 5 average rating, 34 reviews

The Clean Slate, Walk to down town, pet friendly

The Clean Slate is the latest offering from Lake Geneva luxury Rentals. Half mile walk to downtown. Pet friendly The house can accommodate 8 guests, but can be rented with its sister property, The White House, to accommodate larger groups. Contact host to inquire about renting both houses. This newly built home will surely delight. Tastefully decorated with all modern amenities. Easy access to downtown Lake Geneva’s shops, restaurants, Riviera Beach, and Geneva Lake Shore Path.

Guest favourite

Home in Round Lake Beach

4.99 out of 5 average rating, 129 reviews

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!

Superhost

Home in Fox Lake

4.9 out of 5 average rating, 160 reviews

Beach Bungalow Getaway ★ Chain O Lakes

Outdoor enthusiasts will be delighted with this quaint romantic cottage. Walk down to the lake to enjoy boating, swimming, fishing, and more. The fall colors, hiking, and nature setting is especially breathtaking this time of year. Experience all the comforts of home in this newly remodeled lake cottage desirably located on Lippincott Point. Perfect for gathering with friends by the lakeside fire pit, boating “the chain” and all that lake life has to offer!

Guest favourite

Home in Racine

4.91 out of 5 average rating, 134 reviews

The Beach House at Michigan Blvd.

Always Professionally Cleaned, Disinfected, and Absolutely Stunning 5 Bedroom Beach House across from a Top 10 Rated Beach. Relax in this completely renovated and professionally designed home. Enjoy breathtaking views, gorgeous sunrises on the front porch, and luxury accommodations. Walk to the beach, the zoo, downtown, and the marinas. Or, enjoy a relaxing bike ride along the pristine lakeshore. Perfect for any family size or occasion!

Guest favourite

Home in Lake Geneva

4.97 out of 5 average rating, 148 reviews

NEW! Cozy Downtown Farmhouse, 5BR 3 BA Sleeps 15!!

Our gorgeous home is set in the heart of downtown Lake Geneva. 5 bedroom, 3 bathroom home that is two blocks from the lake and a few blocks from downtown shopping and restaurants. We just completed an extensive renovation of the home and it is now ready for you to stay for your dream vacation. Our homes are fully licensed and legal for short term rentals. We also rent the home two doors down and another in nearby Williams Bay!

Guest favourite

Home in Lake Geneva

5 out of 5 average rating, 26 reviews

Modern Downtown Lake Geneva Charm - Sleeps 8

Beautiful 3 bedroom home located in the heart of Lake Geneva and walking distance to restaurants, bars, & the beach. This recently remodeled house is the perfect place for an escape. With an open kitchen concept, leading out to a large composite (Trex®) deck, there is no shortage of space for any activity or just to get back to a quieter more relaxing pace. *** This property is Licensed & Legal for weekend rentals ***

Superhost

Home in Fox Lake

4.88 out of 5 average rating, 117 reviews

Lakefront Paradise

Relax and have fun with the family and friends at this unique getaway! We are situated directly on the lakefront with private access to our pier where you can enjoy world class sunset views. Jump in and go swimming, roast s'mores over a campfire right next to the water, grill up some burgers on the spacious deck or get some rest in our luxurious suites in this newly renovated (June 2021) home.

Superhost

Home in Fox Lake

4.78 out of 5 average rating, 107 reviews

This is a VACATION spot! With a million dollar view! bring your water toys, or just float right off the pier, for wonderful swimming!

This home features, great views for relaxing. Or take the kayak for a morning or afternoon ride, or just jump right in and swim. Bring your own water craft, you can launch and park right on our pier! a short walk to restaurants, shopping, movies ect Great for winter activities also, snowmobiling, ice fishing or maybe just relax in front of the fireplace. There is a ring doorbell.

Guest favourite

Home in Burlington

4.88 out of 5 average rating, 17 reviews

5 Miles to Lake Geneva- Secluded with Game Room

Grandview Point by Stay at Lake Geneva Secluded hideaway with 4000sf of living space. 10 miles of sweeping views of nature and tranquility. A home that's meant to be enjoyed inside and out with a private pool (Memorial to Labor Day weekend only) pool table, wet bar, darts, foosball, ping pong, board games, and a gourmet kitchen.