Pleasant Prairie, Wisconsin Short-Term Rental Market
Pleasant Prairie area STRs averaged $293/night at 60.1% occupancy in June 2026, with revenue up 3.2% year over year.
Quick Answer: Pleasant Prairie, Wisconsin is an active short-term rental market. average occupancy in the Wisconsin Area market area is 60%. average monthly revenue in the Wisconsin Area market area is $4,359. average daily rate in the Wisconsin Area market area is $293. the top operator in the Wisconsin Area market area is Evolve with 553 listings. market score is 80/100 (grade B).
Market data reflects the Wisconsin Area regional market, which includes Pleasant Prairie. Regulations, taxes, and permit details below are specific to Pleasant Prairie.
Market Score Breakdown
Five dimensions StaySTRA evaluates per market.
Market Overview
Pleasant Prairie is a village of about 21,802 residents in Kenosha County, Wisconsin, sitting on the I-94 corridor roughly midway between Milwaukee and Chicago. Visitor demand here is shaped less by a single destination draw and more by a mix of outlet shopping at Pleasant Prairie Premium Outlets, the Jelly Belly Center’s free candy tours, and youth and amateur sports tournaments hosted at the 300,000 square foot RecPlex, one of the largest municipal recreation facilities in the country.
In June 2026, the Pleasant Prairie area short-term rental market averaged 60.08% occupancy and a $293.06 average daily rate, with average monthly revenue of $4,358.88 per active listing. Entire-place listings averaged $301.47 per night, while the small luxury tier commanded $521.70. Year over year, occupancy held nearly flat (down 0.08 points) and ADR softened 2.4%, but revenue still grew 3.23%, suggesting operators are filling more nights at slightly lower rates rather than losing ground overall.
Listing count, bedroom mix, and channel split data for this area are tracked at a shared regional level rather than uniquely for Pleasant Prairie, so this profile omits those specific breakdowns.
The market’s demand pattern reflects its role as a shopping and sports-event destination rather than a classic vacation getaway: bookings lean toward weekend and short-trip stays tied to tournament schedules and retail visits rather than extended vacation blocks.
Seasonal Patterns
| Month | Occupancy |
|---|---|
| Jan | 36% |
| Feb | 41% |
| Mar | 35% |
| Apr | 41% |
| May | 50% |
| Jun | 62% |
| Jul | 70% |
| Aug | 62% |
| Sep | 47% |
| Oct | 43% |
| Nov | 38% |
| Dec | 41% |
Month-by-month nightly rates and revenue figures for Pleasant Prairie are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Top Short-Term Rental Operators in Wisconsin Area market area
Ranked by total active listings. Useful for understanding the competitive landscape. Operator data is published for the Wisconsin Area market as a whole, which includes Pleasant Prairie, so these counts are not Pleasant Prairie-only figures.
| # | Operator | Listings | Reviews | Rating |
|---|---|---|---|---|
| 1 | Evolve | 553 | 19,893 | ★ 4.74 |
| 2 | Vacasa | 371 | 10,250 | ★ 4.62 |
| 3 | Hiller Vacation Homes | 95 | 1,823 | ★ 4.46 |
| 4 | Northwoods Property Managment | 63 | 444 | ★ 4.71 |
| 5 | Wild Eagle Lodge | 59 | 18 | ★ 4.50 |
What Kind of STR Should I Buy in Pleasant Prairie?
Revenue and nightly-rate breakdowns by bedroom count, property tier, and dwelling type for Pleasant Prairie are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Channel Mix
Distribution of bookings across major STR platforms.
| Channel | Share |
|---|---|
| airbnb | 38.3% |
| vrbo | 14.1% |
| both | 47.7% |
Home Value Trends (Pleasant Prairie)
Typical home values, median sale prices, and the 10-year price trend for Pleasant Prairie are available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Booking Insights
Booking-window and length-of-stay analysis for Pleasant Prairie — how far ahead guests book and how to price around it — is available to StaySTRA Pro members. Unlock with StaySTRA Pro or analyze a specific address free.
Short-Term Rental Regulations
Short-term rentals are legal in Pleasant Prairie and regulated under Chapter 320 of the village municipal code. Operators need a village short-term rental permit, which costs just $10 and is renewed annually through the Village Clerk’s Office. Anyone renting more than 10 nights a year must also hold a Wisconsin DATCP Tourist Rooming House (Public Lodging) license, and applicants must submit a copy of that license where applicable.
Lodging is subject to an 8% village room tax on gross receipts. There is no owner-occupancy requirement, no primary-residence requirement, and no stated cap on the number of nights a property can be rented. Structural modifications to create a rental unit trigger Building Inspection and Community Development review.
Enforcement is described as moderate, administrative rather than aggressive, and this is reinforced at the state level: Wisconsin’s right-to-rent law (Wis. Stat. sec. 66.1014, from 2017 Act 59) bars municipalities from prohibiting rentals of seven or more consecutive days and requires that local permits use objective, reasonable standards rather than functioning as a de facto ban. No major local ordinance changes have been identified in the past 24 months. Investors should still confirm current zoning-district allowances and Chapter 320 specifics directly with the village before purchasing.
Market Comparison
Pleasant Prairie’s 60.1% occupancy in June 2026 runs well above the roughly 55% occupancy that is typical across the broader U.S. short-term rental market, and its $293.06 ADR also outpaces the national median of roughly $220. That combination puts this market’s revenue performance ahead of a typical U.S. STR market on paper, even before accounting for its low-cost, low-friction permitting environment.
Property manager data for this area is tracked at a shared regional level rather than uniquely for Pleasant Prairie, so this profile omits naming specific operators here.
What differentiates Pleasant Prairie from many small STR markets is its demand driver: rather than natural scenery or a historic downtown, it draws visitors through built attractions, retail, and organized youth sports, which tends to produce steadier weekday-adjacent demand around event and tournament calendars, on top of the more typical weekend leisure pattern seen elsewhere.
Frequently Asked Questions About Pleasant Prairie, Wisconsin
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Is there a cap on how many nights I can rent my property in Pleasant Prairie?
What occupancy tax applies to short-term rentals in Pleasant Prairie?
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