Holiday rentals in Pleasant Prairie

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pleasant Prairie

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Racine

4.91 out of 5 average rating, 214 reviews

“Rustic Farmhouse Retreat” at a working farm

A charming little farmhouse filled with antiques & eclectic artwork from all over the world. It is situated in the middle of a working farm that raises a plethora of exotic fruits, vegetables, shiitake mushrooms, and flowers for local gourmet restaurants. The house interior has a unique design decorated with beautiful hand crafted stonework accented with exotic driftwood trim from old wooden shipwrecks. Try our outdoor Neapolitan wood fired oven for the best pizza ever. A truly unique getaway!

5–12 Aug

$199 SGD per night
Guest favourite

Apartment in Kenosha

4.93 out of 5 average rating, 170 reviews

Inviting, spacious apt! Ideal for stay & work

This brand new basement apartment is an amazingly pleasant, spacious and private unit (over 950 sq. ft). Whatever the motive of your trip is —work from home, business, family function, wedding, graduation, friends, or simply a vacation escapade — you will enjoy the freedom this space provides. This residential, private neighborhood apartment is carefully designed. The full kitchen, classy bathroom, plush and extra-comfortable king size bed, the TV and all the amenities will fulfill your needs.

16–23 May

$111 SGD per night
Guest favourite

Flat in Kenosha

4.92 out of 5 average rating, 212 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.

12–19 Sep

$138 SGD per night

Popular amenities for Pleasant Prairie holiday rentals

Stay near Pleasant Prairie's top sights

Bristol Renaissance Faire36 locals recommend
Pleasant Prairie Premium Outlets59 locals recommend
Cheddar's Scratch Kitchen3 locals recommend
Brat Stop3 locals recommend
Jelly Belly Center16 locals recommend
The Spot Drive-In17 locals recommend

Other great holiday rentals in Pleasant Prairie

Guest favourite

Home in Kenosha

5.0 out of 5 average rating, 52 reviews

Tu Casa Cottage - Your Home Away From Home

20–27 Apr

$139 SGD per night
Guest favourite

Home in Kenosha

4.96 out of 5 average rating, 69 reviews

Cozy 2 BR home close to Lake and Universities.

21–28 Aug

$159 SGD per night
Guest favourite

Home in Kenosha

5.0 out of 5 average rating, 92 reviews

LITTLE HOUSE by the BIG LAKE

12–19 May

$262 SGD per night
Guest favourite

Flat in Kenosha

5.0 out of 5 average rating, 36 reviews

Remodeled 4 bedroom 2 bath not your typical airbnb

15–22 Nov

$287 SGD per night
Guest favourite

Home in Kenosha

5.0 out of 5 average rating, 26 reviews

Sister House Cottage-Beachy Charm-Driveway Parking

3–10 May

$199 SGD per night
Guest favourite

Home in Kenosha

4.89 out of 5 average rating, 83 reviews

Brand New!!! Cabin style farm house

10–17 Dec

$279 SGD per night
Guest favourite

Apartment in Racine

4.91 out of 5 average rating, 32 reviews

Artist loft in Racine

23–30 Apr

$142 SGD per night
Guest favourite

Guest suite in Union Grove

4.97 out of 5 average rating, 75 reviews

Peaceful Horse Farm Retreat

17–24 Nov

$207 SGD per night
Superhost

Tiny home in Beach Park

4.82 out of 5 average rating, 61 reviews

Tiny home in not so tiny Yard

25 Jun – 2 Jul

$211 SGD per night
Guest favourite

Guest house in Lake Forest

4.95 out of 5 average rating, 93 reviews

The Green Door - safe and calm with walkability

29 Jan – 5 Feb

$133 SGD per night
Superhost

Home in Kenosha

5.0 out of 5 average rating, 9 reviews

Spectacular Lake Michigan views

7–14 Sep

$413 SGD per night
Superhost

Home in Pleasant Prairie

5.0 out of 5 average rating, 9 reviews

Lakehouse Escape! 2 Bedroom, 1.5 Baths, Private!

12–19 Jul

$549 SGD per night

Quick stats about holiday rentals in Pleasant Prairie

Total rentals

30 properties

Rentals with dedicated workspaces

20 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

1.4K reviews

Nightly prices starting at

$54 SGD before taxes and fees

Destinations to explore