Family-friendly holiday rentals in Pleasant Prairie

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Top-rated family-friendly rentals in Pleasant Prairie

Guests agree: these family-friendly homes are highly rated for location, cleanliness and more.

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Guest favourite

Home

4.93 out of 5 average rating, 155 reviews

"About Time" You will love it! -12 beds

We are SUPERHOSTS !!!- Look for all inclusive boat and wave runner packages through Twin Lakes Boat Rental. Swimming at the Sand Bar in the middle of the lake or at Lake Mary’s beach in Twin Lakes is best for kids. About Time has a spacious yard for corn hole/wiffleball, basketball, Kayaks & SUP's. There’s a large playfield is just 200 yards East too. Visit the Sand Bar Restaurant also, a must! The spring fed clear water is great for fishing & skiing. We love this place and know you will too.

Guest favourite

Flat

4.92 out of 5 average rating, 236 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.

Superhost

Guest suite

4.95 out of 5 average rating, 73 reviews

Clean Country living at its best!

Beautiful Country Farm property on twenty acres that breathes peace, tranquility and cleanliness surrounded by Lake County Forest Preserves. A perfect place for fresh air and Vitamin D to rest and enjoy the company of your loved ones! Also located minutes from the beautiful Chain 'O Lakes, Fox River and several forest preserves, only a short drive to quaint little down towns of Antioch, Lake Villa and more not to mention a ten minute drive to Wisconsin and only 13 minutes West of Gurnee.

Superhost

Home

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.

Superhost

Chalet

4.84 out of 5 average rating, 385 reviews

"A" Frame Brandenburg Lake

Getaway to a cozy 1 bedroom w/loft for 2, up to 6 people. Full kitchen 1.5 bath all season getaway. There is a piano as well. A tranquil home steps from a private lake. Oak and Pine surround you plus a stone fireplace, it feels like the North Woods. The A Frame guest house shares a 5 acre compound ( total 20 Acres) with the owners residence and caretaker cottage. The Volo Bog 800ft away. No hot tub Nov - May. Swimming pool usually June-October often cool to use in early June.

Superhost

Bungalow

4.87 out of 5 average rating, 204 reviews

Quaint Bungalow, near Great Lakes Naval Base

This cozy bungalow is located 41 miles north of Chicago; 60 miles south of Milwaukee, WI; and just 12 miles west of Great Lakes Naval Base. Nearby train stations make Chicago just a 45-minute train ride away. O'Hare Airport is a 30-40 minute commute from our home. Additional nearby sites include Great America, and shopping venues--from outlet malls in Gurnee and Kenosha, to quaint downtowns, like Libertyville. Location makes this home an ideal venue for Midwest sightseeing.

Guest favourite

Flat

4.91 out of 5 average rating, 275 reviews

WAVES : Steps to the Harbor ~ Crash Here!

Welcome to "Waves Apartment," your ideal retreat by the harbor. This cozy apartment offers three queen-sized beds, two baths, and conveniences like onsite parking and a private deck. Enjoy the comfort of three bedrooms, two baths alongside an open living/dining area with scenic lake and harbor views. The fully equipped kitchen and laundry facilities ensure a hassle-free stay. Experience a blend of comfort and convenience, designed for your enjoyment.

Guest favourite

Home

4.94 out of 5 average rating, 156 reviews

Root River Home - Waterfront property - Sleeps 8+

Beautiful waterfront escape awaits you. Located along the Root River, Village of Caledonia, WI (Racine County) 10 Minutes / 3 Miles from North Beach (Lake Michigan) and only 5 minutes from Quarry Lake Park (Swimming and Recreation Area). Includes Kayaks, Canoes, Row Boat, Paddle boat, Firewood, Gas Grills, Netflix, WIFI, TV, and Wi and Playstation for the Kids, Ping Pong Table, outdoor firepits and much much more.

Guest favourite

Cabin

4.82 out of 5 average rating, 625 reviews

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.

Guest favourite

Home

4.95 out of 5 average rating, 193 reviews

Historic Racine Property! - The Parish House

Stay in a little piece of history in Racine, WI! Built at the end of the 1800’s for George Murray and his family, this portion of the Murray Mansion functioned as the servant’s quarters for the family home. Minutes away from downtown Racine and some of the most stunning beaches on Lake Michigan, this renovated historic home is the perfect escape for your stay in Wisconsin.

Superhost

Home

4.83 out of 5 average rating, 103 reviews

Beautiful Lakehouse sleeps 12 Boat/Pets/HotTub/Ski

Discover the perfect lakeside retreat just an hour away from both Chicago and Milwaukee! Our fully equipped home on the stunning Lake Shangrila offers a spacious, comfortable stay for up to 12 guests. While our home and the lake will provide your group endless entertainment, you will also be located in an area surrounded by various attractions available in every season.

Guest favourite

Home

4.94 out of 5 average rating, 146 reviews

The Retreat on Lake Michigan 6 bd/4bth 4000 sq ft

*** Please for 2025 a 7-night Friday-Friday reservation is required during peak season from June 13-August 15. *** The best revenge for hard work is harder relaxation, and the ideal getaway is The Retreat, a luxurious and scenic waterfront property where you and your guests are encouraged to relax, reward, and pamper yourselves in splendor.