Family-friendly vacation rentals in Pleasant Prairie

4.96 out of 5 average rating, 198 reviews

An open living area features a cozy workspace with a desk and chair beside a vibrant area rug. Natural light filters through large windows, illuminating a relaxed seating space with a lamp and plants. The adjoining kitchen with blue cabinets and a cart is visible in the background.

Loft in Woodstock

Curated Loft Retreat in The Heart Of Woodstock

Welcome to our spacious upper retreat with modern conveniences. We have great WiFi for you to stay in touch with and are well stocked with books for you to enjoy time unplugged. Close to the Historic Square (you may have seen it in the movie Groundhog Day) you can easily walk to unique shops, cafes, and restaurants. Our curated timeless decor is filled with storied items from our travels, and photos we've snapped locally. Come renew yourself here. We can't wait to share Woodstock IL with you.

4.81 out of 5 average rating, 114 reviews

A charming brick house is surrounded by well-maintained landscaping, featuring various green shrubs and white flowering plants. The front yard offers a neat lawn and a flower bed with stones. The adjacent houses are visible, showcasing a friendly neighborhood vibe.

Guest suite in Bay View

Basement Bay View Suite,express bus airport-north

Bay View is a walking community. Our place is close to family-friendly activities, public transport, & the airport. You’ll love our place. It's a short walk to express bus from airport, past downtown, UW-M and to Bayside. Located across the street from Humboldt Park. We are about a 20 minute walk from Lake Michigan. Summerfest grounds a short bus ride away. Winter is fun in the park. Tobogganing (2), skates and cross country skis to use. Hope the sizes fit you. I find if one plays in snow ⛄️ 😌

4.93 out of 5 average rating, 248 reviews

The image depicts a vibrant storefront building surrounded by trees and brightly colored flowers. The entrance features large windows and a doorway with a sign that indicates 15 years of celebration. A cobblestone path leads to the entrance, with a glimpse of a neighboring building in the background.

Apartment in Kenosha

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.

4.92 out of 5 average rating, 277 reviews

A charming coastal home is presented with shingle siding and a large covered porch. Lush greenery and flowering plants accentuate the front yard, while a tree stands centrally, framed by the inviting facade of the residence. The pathway leads to the inviting entrance.

Home in Kenosha

Hot tub getaway Extra Large capacity home

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.

4.84 out of 5 average rating, 389 reviews

A winding red mulch pathway leads towards a charming A-frame house nestled among tall trees. The surrounding lawn is lush and green, with a peaceful natural setting enhanced by the canopy of leaves above.

Chalet in Ingleside

"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.

4.87 out of 5 average rating, 212 reviews

A charming bungalow exterior presents a warm facade with well-maintained landscaping. Features include a welcoming front staircase with wrought iron railings, potted flowers under large windows, and a flag hanging from the porch. A lush green lawn surrounds the home, enhancing its inviting presence.

Bungalow in Mundelein

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 suite in Highland Park

A modern kitchen features sleek cabinetry and granite countertops, with an island and two bar stools. Stainless steel appliances, including a refrigerator and stove, are prominent. Soft overhead lighting enhances the neutral color palette, and an adjacent pantry is visible through an open door.

4.97 out of 5 average rating, 146 reviews

Charming in-law suite w/ use of deck and yard

Charming home in Highland Park. The space is my in-law suite which is in the lower level of my home and has its own full size kitchen and bathroom. We live up-stairs with our 3 little dogs so we will be available if you need anything during your stay. The in-law suite is set up like a studio and has one queen bed,a separate closet area and laundry. Please note- the suite is in the basement, but there is natural light. You have shared use of the deck/yard if desired.

4.91 out of 5 average rating, 332 reviews

A cozy living room features a gray sofa paired with an accent chair in a patterned fabric. Natural light pours in through a large window, illuminating the hardwood floor. Stained glass windows add colorful detail to the space, complemented by a wooden coffee table with decorative items.

Apartment in West Allis

The Cheese House

Large well appointed two bedroom, living room, dining room, kitchen, and private balcony. Apartment is located on the second floor right above the award winning West Allis Cheese & Sausage Shoppe. Each stay includes 4 breakfast sandwiches and house coffee vouchers for the cheese store cafe. The rental is centrally located minutes from Pettit National Ice Center, Milwaukee County Zoo, Wisconsin State Fair, and Brewers Stadium not to mention local restaurants.

4.94 out of 5 average rating, 161 reviews

A spacious backyard is framed by tall trees, providing ample shade. A set of colorful kayaks and canoes is neatly arranged on a rack. Steps lead up to a charming house, while outdoor seating options are visible near a firepit, allowing for relaxation and social gatherings.

Home in Racine

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.

4.83 out of 5 average rating, 661 reviews

A rustic cabin with a wooden exterior is situated near Lake Michigan. A wooden deck leads down to the water, providing easy access for outdoor activities. Lush green grass surrounds the cabin, and trees offer natural shade, creating a serene lakeside atmosphere.

Cabin in Kenosha

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.

4.94 out of 5 average rating, 115 reviews

The open-concept living area features a modern sofa with patterned pillows, a glass coffee table, and sleek cabinetry. Light-colored walls and recessed lighting enhance the spacious feel. A dining area with high chairs and a desk sits nearby, creating a functional and inviting space.

Apartment in Racine

The Hive 2BR Apt | Downtown Racine Escape!"

The Sunrise View apartment, situated upstairs in the historic 413 1/2 6th Street building, exudes privacy and comfort. Lightly styled with a modern flair and subtle bee-themed touches, this space offers an open-concept living area, two spacious bedrooms, two bathrooms, and a fully-equipped kitchen with island seating. Smart TV's are provided and you can stream from your own accounts.