Holiday rentals in Pleasant Prairie

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Top-rated holiday rentals in Pleasant Prairie

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Superhost

Villa in McHenry

4.95 out of 5 average rating, 21 reviews

Fabulous Cabin

WELCOME TO WATERFRONT LOG-SIDED HOME! ARTISAN CRAFTMANSHIP HOME OFFERS A BACKYARD OASIS SITUATED , NESTLED ON A PRIVATE POND, Heated POOL(closed till April 1st), Hot tub open from Oct 15th to Apr 15thGAZEBO, FIRE PIT, FISHING! 4 BEDROOMS AND 4.5 BATHS The homes sits on the highest point in the neighborhood and has stunning views in the front & backyard! Enjoy the mornings sitting on your front porch. The main floor is completed by an office, finished walkout basement in with a custom built bar

Guest favourite

Bungalow in Lake Geneva

4.99 out of 5 average rating, 134 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, 261 reviews

A Home for your Holiday! Hot tub/Chefs Kitchen

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, 33 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, 125 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, 159 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, 133 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, 144 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, 25 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, 115 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

Cottage in Antioch

4.83 out of 5 average rating, 166 reviews

#1 The Lodge @ The Cottages on Petite Lake

This beautiful and spacious lakefront lodge has views, charm and wonderful amenities. Enjoy your morning coffee with a beautiful sunrise from your private deck right over the water. Spend your days on the lake with the beach just steps away. End the night with a bonfire or movie in the comfortable great room.