Family-friendly holiday rentals in Pleasant Prairie

Find and book unique family-friendly homes on Airbnb

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 in Bay View

4.95 out of 5 average rating, 111 reviews

This Must Be the Place- Bayview Bohemian Vibes

Perfect for families! We have a cozy light filled home in a quiet walkable neighborhood of Bayview. Enjoy the back porch with a coffee or local brew. We are a 5 minute drive from the airport, 10 min to downtown Mke and 5 minute walk to public transit. Parks are in walking distance as well as cafes & restaurants. Our home is a great place for couples, solo adventurers, business travelers, families, groups, and furry friends (Fee of $150 up to two well behaved dogs) Relax, unwind & enjoy our home!

Guest favourite

Home in Richmond

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.

Top guest favourite

Flat in Kenosha

4.93 out of 5 average rating, 241 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.

Top guest favourite

Apartment in Lake Geneva

4.91 out of 5 average rating, 105 reviews

Top location, no cleaning fee, everthings close B

If you want the best of Lake Geneva from the one of the hottest locations in the city this then you will love staying here! You are a block from great restaurants, bars, the Riviera docks, the Riviera beach, boat rentals, shopping, and more. You'll park your car in our free parking and not need it for the rest of your stay. Relax in your private suite, or sit and enjoy the outdoor balcony with a beautiful view of the lake and downtown. When you’re ready to enjoy the town, simply step outside

Superhost

Home in Kenosha

4.92 out of 5 average rating, 270 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.

Top guest favourite

Flat in Lake Geneva

5 out of 5 average rating, 239 reviews

Downtown Geneva Street Getaway

Geneva Street Getaway is one block from downtown and 2 blocks to the beach!! The unit consists of the entire, private first floor. It has 2 bedrooms (1 king- 1st and 1 queen -2nd) 2 full bathrooms, 2 common areas with sleepers (queens with gel memory foam mattresses), and a kitchenette, to accommodate 8. The décor is tasteful, bright, and airy. Licensed and approved by the city, our comfortable home is within steps of downtown restaurants, bars, shopping, boat rentals, and the beach!

Superhost

Home in Cudahy

4.83 out of 5 average rating, 101 reviews

Wonderful Family Home Across from Park

Extended Stays Welcome! Everything you could want in a home away from home. Our place is a comfortable and beautifully updated mid-century brick ranch on a quiet tree-lined street overlooking 36-acre Greene Park. Super convenient location, just 10 min from both the airport and downtown. Walkable to Lake Michigan and just down the road from Bay View's great restaurants and nightlife. Pet-friendly and perfect for families, small groups, or business travel. You'll feel right at home here!

Superhost

Chalet in Ingleside

4.84 out of 5 average rating, 387 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

Flat in West Allis

4.78 out of 5 average rating, 189 reviews

Station No 06 Inn

Very spacious two bedroom condo style apartment completely remolded and updated. Located behind Wild Roots restaurant which offers fine dining in a casual setting. The Award Wining West Allis Cheese & Sausage Shoppe (deli & cafe), Station No 06 beer garden, and Becher Meats are across the street. Once you arrive you won't need to leave, and you get two free breakfast sandwiches and house coffee per adult per stay at the cheese shop are amazing!

Guest favourite

Home in Racine

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.

Superhost

Home in Bay View

4.76 out of 5 average rating, 139 reviews

Peaceful home in beauitful Bayview!

Enjoy the best that Bay View has to offer! Located in a quiet neighborhood just blocks from the lakefront and Kinnickinnic Ave, lined with cafés, restaurants, and bars, this modern and spacious house is the perfect home away from home. Fully furnished kitchen, finished basement, back patio, washer/dryer, office den. Pets considered. 10 minute drive from downtown or the airport.

Superhost

Home in Bristol

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.