We Started as Homeowners. We Never Forget It.
Winter Park Management was built from a lot of lessons learned through personal experience.
A passion for the mountains. A commitment to excellence. Winter Park is not just where we work, it’s where we live, play, and build lasting relationships. Over the years, we’ve grown from managing a single home to over 100. Through it all, our core values have remained the same: honest service, attention to detail, and a deep respect for both our homeowners and guests. Whether it’s welcoming travellers to a cozy mountain retreat or helping homeowners unlock the full potential of their properties, our mission is simple—to provide a seamless, high-quality experience every step of the way.
Our story
Built by Homeowners, for Homeowners
Like many vacation homeowners, we dreamed of enjoying the mountains while generating rental income. In 2005, we purchased a ski-in/ski-out home at Iron Horse Resort, expecting a seamless experience. But the reality fell short—the on-site rental program lacked the personal care we envisioned, the service was inconsistent, and the financial results weren’t optimized.
Determined to do things differently, we took matters into our own hands. We fine-tuned our approach, ensuring each guest received a high-quality experience while implementing strategic pricing and meticulous property care. It wasn’t long before other homeowners took notice. They saw how we maximized revenue while keeping our home in pristine condition, and they began asking if we could do the same for them.
In 2007, Winter Park Management was born from a simple belief. If you treat every home like it’s your own, everything else follows. Nineteen years later, that belief hasn’t changed.
Why Stay With Winter Park Management?
Handpicked Homes
Thoughtfully designed stays, from cozy cabins to sleek mountain lodges
Effortless Stays
Seamless booking, easy check-in, and hotel-quality housekeeping
Prime Locations
Slopeside retreats, secluded getaways, and homes near downtown Winter Park
Personalized Service
Locally managed, 24/7 guest support, and real-time recommendations tailored to you
why homeowners choose us
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Maximize Your income
Earn up to 80% more while renting fewer nights
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Smarter Marketing & Premium Bookings
Targeting high-quality travelers locally & internationally
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Guest Screening & Property Protection
Ensuring your home is treated with care
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FiveStar Housekeeping & Maintenance
Keeping your home pristine and guest-ready
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Total Transparency
Access real-time booking data & earnings reports anytime
Locals Who Know Winter Park Best
We don’t just manage properties here. We live here
From the best ski runs to hidden hiking trails and top après-ski spots, our team knows Winter Park inside and out. Whether you’re visiting for a winter adventure or a summer escape, we help you make the most of your stay with personalized recommendations and local expertise.
Experience Winter Park like a local.
Need insider tips? We’re just a call or message away.
