Winter Park Property Management

Winter Park Property Management

Meet Your Host!

With over 110 glowing reviews and an average 4.9-star rating, Winter Park Property Management is proud to offer a top-tier hosting experience built on professionalism, care, and local expertise. As a seasoned property manager, I specialize in maximizing efficiency, protecting your investment, and ensuring every guest enjoys a five-star stay. From seamless operations to personalized service, my goal is to take the stress out of vacation rental management—so you can enjoy the rewards without the hassle.

Let’s connect to explore how I can help manage your property with the same attention and excellence my guests have come to love!

Real Talk From Real Guests…

Trailside Escape - Guest February 2025

“My friends and I really enjoyed our stay! The place was cozy and very clean. Matthew was very responsive and a great help. The location is beautiful. You can’t go wrong with this spot. Also it’s perfect if you plan to go to Winter Park. There is a shuttle super close by!”

Arrow 216 - February 2025

“This place was perfect for our family of 4. It was extremely comfortable, spacious and clean. The location was perfect for of ski vacation without a car! The town is walkable and the shuttle to Winter Park was practically across the street. One of our best stays in an airbnb!”

Arrow 216 - February 2025

“This new unit was an absolute gem! Beautifully appointed and incredibly comfortable, it had everything we needed for a relaxing, long ski weekend in Winter Park. The kitchen was a dream to cook in, with top-notch appliances that made making meals very fund. It even has a top of the line Breville Convection Toaster Oven Air Fryer. Super pet-friendly—our dog loved it, and the provided crate for medium to large dogs was a great touch. We don't have children but it is clear that the host has made efforts to welcome families with small children. The location was perfect, with a bus stop just steps away offering free service to Winter Park Resort. After a day on the slopes, the spacious hot tub on the deck was the perfect place to unwind. Plus, the host was fantastic—very communicative and helpful throughout our stay. Highly recommend!”

Trailside Escape - Janurary 2025

“Unit was excellent and much nicer than the pictures. Lots of space and high ceilings it met our needs perfectly. Great location and only took about a minute walk to get to the bus which took us everywhere we needed to go. Also had garage parking away from the elements that fit our large truck. Thanks to the location, we didn’t need to drive anywhere the entire week of our stay. I would absolutely recommend this place to anyone and would stay again if we have the chance.”