Sheboygan Vacation Rentals
Sheboygan, WI
Jeremy Udovich wasn’t new to hospitality, but stepping into STR management with his wife and sister took things to a new level. In just a few years, they’ve built one of the most efficient teams in our entire portfolio, managing 16 high-quality lakefront homes with nearly no full-time staff. Since partnering with Freewyld Foundry for Revenue & Pricing Management, they’ve seen a 30% increase in total revenue with no change in properties or team size.
Before RPM:
$467K
After RPM:
$608K
Growth:
%
Owner-operator turned boutique PM
Grew from 1 to 16 properties in under 3 years through word-of-mouth and reputation
30% revenue growth YoY across same-property set
Jeremy came to STRs with a background in hospitality and a mindset forged through real-world adversity. He didn’t scale by chasing every unit. He hand-picked homes that could consistently deliver five-star experiences. But even the best-managed homes need pricing power to reach their potential.
Before partnering with RPM, Jeremy was already using dynamic pricing tools, but gut feel still played a big role. Since shifting pricing strategy to be fully data-driven, Sheboygan Vacation Rentals has seen performance take off. Their same-property portfolio saw a 30% increase in revenue YoY, all while Jeremy continued working his full-time job and managing the business with a small, nimble team.
With smarter seasonal pricing, tighter LOS rules, and better occupancy pacing, his team captured high-value bookings without sacrificing quality or reviews.
His mindset? “You can charge anything… if you deliver.” And Sheboygan Vacation Rentals delivers. From sauna-equipped luxury lake homes to ghost-hunting guests in their original cabin, they’ve built a business that wins repeat guests, glows with five-star ratings, and outpaces the competition.
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