Nestled in the heart of Colorado’s mountain landscape, Winter Park has long been a haven for travelers seeking the perfect balance of adventure and tranquility. Behind every unforgettable stay, however, lies an intricate network of care, precision, and vision. It takes more than beautiful scenery to deliver an exceptional vacation experience—it takes thoughtful management, attention to detail, and a deep understanding of what makes a getaway truly special.
At the center of this vision stands David Repka, the Founder of Winter Park Escapes. Blending his entrepreneurial spirit with firsthand experience as a homeowner and rental operator, David Repka has transformed how property management is experienced in Winter Park. Under his leadership, the company has become a trusted name in luxury vacation rentals, earning recognition as the best management company in Grand County for several consecutive years. His dedication to service excellence and innovation continues to redefine what homeowners and guests can expect from Colorado’s premier vacation destination.
Growing Excellence in Vacation Rental Management
20 years ago, David Repka identified a unique opportunity in the Winter Park, Colorado market when he began renting out his two-bedroom ski-in/ski-out condo. Managing the rental process independently, he quickly recognized the complexities and demands involved but also saw the significant potential for steady income. This hands-on experience laid the foundation for his deeper understanding of vacation rental management.
Drawing on this personal journey, David Repkaestablished Winter Park Escapes, a boutique property management company dedicated to helping other homeowners unlock the full earning potential of their investments. “We currently manage 250 properties with the same dedication and success that started it all,” David Repka explains. His company provides a comprehensive suite of services—from marketing to maintenance—allowing property owners to maximize rental income while enjoying peace of mind. This commitment to excellence has made Winter Park Escapes a trusted leader in the local vacation rental market.
Ensuring Excellence in Vacation Property Management
Winter Park Escapes is a leading vacation management company specializing in luxurious rental properties ranging from ski-in, ski-out condos at the resort base village to custom mountain homes, offering guests a welcoming retreat for an ideal vacation experience throughout the year.
David Repka personally selects each property, focusing on luxury two-bedroom and larger homes mainly suited for families. This careful selection ensures top-quality accommodations, prime locations, excellent amenities, and exceptional white-glove service. The company handles everything from obtaining short-term rental permits to ensuring HOA compliance. Its comprehensive management package includes essentials such as towels, linens, guest supplies, seasonal deep cleaning, hot tub and snow removal services, and general maintenance. Dedicated housekeepers and maintenance staff are assigned to each property, providing personalized care and avoiding the issues that come with rotating teams.
This approach allows homeowners to avoid surprise costs while maintaining their properties at the highest standard, backed by David Repka commitment to excellence and guest satisfaction.
Personalized Services for a Seamless Stay
Winter Park Escapes aims to provide a luxurious living experience for all its guests. The company offers a range of services, such as grocery delivery, private chefs, mobile massage therapies, and ski equipment rentals right at the property to ensure a smooth, high-end stay.
A unique benefit of booking with Winter Park Escapes is its new RAD program (Rentals, Activities, Discounts) that include discounts for activities, equipment rentals, restaurants and transportation at some of the top attractions the area has to offer. Partnerships supporting local businesses is a priority to Winter Park Escapes and ensures guests ‘feel like a local’ by knowing where to enjoy their time for the duration of their stay. .
Winter Park Escapes: Excellence in Vacation Rental Management
- Prime Location: Grand County, Colorado—year-round adventure hub
- Luxury Rentals: Handpicked properties with stunning views
- Wide Variety: Accommodations for every vacation style and group size
- Exclusive RAD Program: Discounts on activities, dining, rentals & transport
- No Hidden Fees: No security deposit or booking fee
- Loyalty Rewards: Returning guest discounts
- Support 24/7: Around-the-clock reservation help
- Easy Access: Keyless entry & direct check-in
- Flexible Booking: Cancel up to 14 days before arrival
- Best Price Guarantee: Save by booking direct
- Immaculate Cleaning: Premium towels and linens professionally cleaned
- Complimentary WiFi: High-speed internet throughout
- Award-Winning: Year over year, voted Best Management Company in Grand County, in addition to top10 national awards and recognitions.
- Optional Extras: Grocery shopping, private chefs, equipment rentals, massages
- Save Up to 50%: Best prices on top rentals and locations
Streamlined Property Onboarding and Guest Assurance
Winter Park Escapes recognizes that preparing a property for rental—including furnishing and stocking essential items like silverware—can be a challenging process for homeowners. To ease this, the company provides extensive support with no setup or onboarding fees, making it simple for property owners, especially first-timers, to have their homes rental-ready.
“We take a highly streamlined and tech-driven approach to onboarding homeowners and preparing their properties for rental. Our dedicated onboarding team works closely with homeowners to ensure everything is in place and ready for guests, and we offer this service without any additional fees. It’s part of our comprehensive program,” says David Repka. Each homeowner receives a welcome packet containing a checklist of essential items needed for the property. For out-of-town owners, Winter Park Escapes can assist in ordering these items. Before listing, the team conducts a walkthrough to confirm readiness and address any remaining needs.
The company also employs in-house designers who help homeowners enhance their properties, whether through full redesigns or refreshing specific rooms. This design expertise adds significant curb appeal, helping properties stand out in a competitive market. Additionally, Winter Park Escapes offers flexible cancellation policies for guests up to 14 days before arrival and does not require a security deposit. Instead, each reservation includes $3,000 in accidental damage coverage, providing peace of mind for both homeowners and guests.
Strengthening Rentals through Expert Partnership
A homeowner with a large custom property at the base of the ski resorts had owned it for several years. As their children grew older and used the property less, they decided to rent it out. Initially, they managed the rentals themselves, but soon found the demands overwhelming, including property upkeep, guest management, reviews, maintenance, housekeeping, and adhering to local rules.
Eventually, they contacted Winter Park Escapes through a referral. The company onboarded them and made strategic improvements to their marketing and added amenities to enhance the property’s appeal. Within six months, the homeowner saw rental income rise by nearly forty percent. They valued the full-service support so much that they referred two friends to Winter Park Escapes, creating a successful partnership for all involved.
Dedicated to a Greener, Cleaner Future
David Repka states, “Sustainability is something we, as a company, take to heart, and feel it’s our responsibility to do our part to keep the mountains beautiful and pristine, making positive impacts where we can.” Winter Park Escapes has made significant progress in adopting sustainable practices with a strong focus on reducing plastic waste and promoting environmentally friendly choices.
A key part of its efforts is eliminating single-use plastics, understanding the harm these cause to the environment and marine life. The company has replaced such plastics with alternative packaging and encourages reusable options across its properties. Additionally, it ensures that all bath and body products used in its rentals are free from microplastics, carefully selecting items that align with its eco-friendly values.
Winter Park Escapes continues to explore new ways to advance its green initiatives through ongoing innovation and commitment. It seeks to lead by example in sustainability, inspiring others while contributing actively to preserving the mountain community for future generations through transparent communication and dedicated environmental efforts.
AI-Powered Marketing for Targeted Outreach
Winter Park Escapes recognizes the growing impact of artificial intelligence (AI) in various industries, including hospitality. The company embraces AI to enhance its marketing efforts, improve data collection, and facilitate better communication with both homeowners and potential guests.
By using social media, Winter Park Escapes highlights the unique charm and beauty of its properties and the surrounding attractions. Through targeted marketing campaigns, the goal is to answer the question, “Why travel to Winter Park and stay at your home?” The company makes booking simple by incorporating direct calls to action like QR codes and quick links, enabling potential guests to reserve their stays easily.
AI plays a vital role by providing insights into guest behavior and preferences. Tracking popular amenities and booking trends allows Winter Park Escapes to tailor its marketing strategies effectively. The company also encourages homeowners to participate on social media, valuing their feedback to strengthen these efforts and expand its online reach. This focus on data-driven marketing and community engagement helps the company connect with the right audience and boost bookings.
Dedicated Team Delivering Personalized Care
For the past 20 years, Winter Park Escapes’ dedicated team has played an essential role in managing properties efficiently. Their deep market knowledge is a significant strength of the company. The team operates through specialized departments, including homeowner relations, onboarding, marketing, guest services, operations, maintenance, and housekeeping. This organized structure helps streamline processes and deliver excellent service.
“We offer 24/7 availability, which our homeowners greatly appreciate. They can reach out at any time and speak with someone who can assist them directly. This level of accessibility and expertise is something we take immense pride in,” says David Repka .
Commitment to Growth and Environmental Care
Looking ahead to the coming 20 years, Winter Park Escapes is enthusiastic about continuing its growth and commitment to excellence, benefiting homeowners, guests, and preserving the natural beauty of Winter Park. Through ongoing innovation, a strong dedication to sustainability, and a passion for delivering outstanding experiences, the company is well-positioned to adapt to the changing travel industry.
David Repka concludes, “We’re here to stay, and we’re here to make a difference. We love Winter Park, and our goal is to preserve its beauty and appeal for generations to come.”
Open Letter to Fellow Hospitality and Property Management Leaders
Dear Industry Colleagues,
Over the past 20 years, I’ve learned that true hospitality is not just about beautiful locations or high-end amenities—it’s about trust, consistency, and care. Every guest and homeowner places their confidence in us, and it’s our responsibility to honor that with integrity, precision, and innovation.
My advice is simple: never compromise on quality, no matter the scale of growth. Invest in people, not just processes—your team is your greatest asset. Embrace technology, like AI, not to replace the human touch but to enhance it. Sustainability is no longer optional; it’s our duty to protect the places that fuel our livelihoods. And above all, focus on creating meaningful experiences, not just transactions.
Success in our industry isn’t built overnight—it’s built by earning trust again and again, one stay at a time.
Sincerely,
David Repka
Founder & CEO
Winter Park Escapes
5 Key Takeaways from David Repka’s Inspiring Leadership at Winter Park Escapes
- Founder’s Vision Built on Experience: David Repka successfully transitioned from being a hands-on rental owner to founding Winter Park Escapes, leveraging his personal property management expertise to create a highly trusted, award-winning company.
- Commitment to Quality and Niche Focus: His leadership emphasizes personally selecting larger, luxury, family-friendly properties in prime locations, ensuring a consistent standard of excellence and superior guest experience.
- Comprehensive Service Maximizes Owner Value: David Repka created a full-service model that handles everything for homeowners—from marketing to maintenance and compliance—resulting in significant income increases (e.g., a 40% rise for one client).
- Innovation in Guest Benefits and Technology: He drives innovation by offering unique perks like the RAD discount program and implementing AI-powered marketing to ensure targeted outreach and efficient operations.
- Leading with Integrity and Sustainability: David Repka prioritizes ethical growth, stressing the importance of trust and consistency in his “Open Letter,” while actively promoting sustainability by eliminating single-use plastics to preserve the mountain environment.
