Owning a property in the scenic mountains of Winter Park, Colorado, offers more than just breathtaking views—it’s an opportunity to earn significant income through vacation rentals. Eighteen years ago, homeowner Dave Repka recognized this potential when he rented out his two-bedroom, ski-in/ski-out condo. Over the next few years, he managed the entire rental process himself and achieved impressive returns.
Today, Repka leverages his experience to help other property owners in Winter Park maximize the earning potential of their investments through Winter Park Escapes, a premier vacation rental management company that transforms properties into thriving income sources.
“We currently manage 225 properties with the same dedication and success that started it all. As a trusted name in vacation rental management, we handle everything—from marketing to maintenance—so the property owner can enjoy maximized rental income without the hassle,” says Repka, owner.
The company is highly selective in the properties it manages, with Repka personally handpicking each one and turning away properties that don’t meet his standards. The focus is on two-bedroom and larger properties catering primarily to families. This approach aims to provide the highest quality accommodations, locations, amenities, and white-glove services available, allowing the company to build an impressive inventory of rentals.
Well-Regarded in Vacation Rental Management
Homeowners often underestimate the demands of managing a vacation rental. According to Repka, it’s not simply about listing the property; it’s a full-time commitment that requires constant attention. Many who attempt to manage it themselves quickly realize how overwhelming the task can be. That’s where Winter Park Escapes, a full-service property management company, comes in. It manages every detail, ensuring homeowners have peace of mind without lifting a finger.
Drawing from his own experiences as both a homeowner and vacation rental owner, Repka offers keen insight into what works and what doesn’t. Under his guidance, Winter Park Escapes has been voted the best management company in Grand County for consecutive years—a testament to the specialized luxury accommodations available in the Winter Park area.
From acquiring short-term rental permits to maintaining compliance with HOA regulations, the company manages it all. Its management program has proven successful in eliminating surprise costs for homeowners by encompassing a comprehensive range of services. This package includes essentials like towels, linens, guest supplies, seasonal deep cleans, hot tub maintenance, snow removal, and general maintenance, providing significant cost savings for homeowners. To further ensure that properties are well-maintained and that any issues are promptly addressed, dedicated housekeepers and maintenance personnel are assigned to each property. This personalized approach helps avoid the pitfalls of a rotating team, which can lead to overlooked details.
On the Tenant Side
Providing a luxury living experience is the goal of Winter Park Escapes. Whether it’s arranging groceries, hiring a private chef, offering mobile massage services, or renting ski equipment directly at the property, the company guarantees that guests enjoy a seamless, high-end experience.
One notable advantage offered by Winter Park Escapes is that it is the only management company in the Winter Park area providing $500 worth of free activities daily for guests. These activities, tailored to both summer and winter seasons, include horseback riding, mountain biking, ski rentals, shuttle services to Denver International Airport, whitewater rafting, zip-lining, and more. Unused activity passes are provided as additional perks to homeowners throughout the year.
Flexibility and Peace of Mind for Homeowners and Guests
Winter Park Escapes understands that setting up a property— everything from furnishing to stocking essential items like silverware—can be overwhelming. That’s why it offers comprehensive support without any setup or onboarding fees, ensuring that properties are rental-ready with minimal stress for homeowners, especially those entering the vacation rental market for the first time.
“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 Repka.
For every homeowner, Winter Park Escapes provides a welcome packet that includes a checklist of essential items needed to get the property rental-ready. For those who are out of town, the company can even assist with ordering these items. When a property is nearly ready, the team conducts a walkthrough to confirm that everything is in order and to address any outstanding needs.
The company also has in-house designers who excel in helping homeowners improve the look of their properties, whether through complete redesigns or refreshing individual rooms. This expertise adds significant curb appeal and ensures that properties stand out in the competitive resort market.
The company offers flexible cancellation policies for guests up to 14 days before arrival and doesn’t charge a security deposit. Instead, it includes $3,000 of accidental damage coverage with every reservation, giving both homeowners and guests extra peace of mind.
A Personal Retreat Turned into a Profitable Investment: A Homeowner’s Success Story
Winter Park Escapes had a homeowner with a large custom home at the base of the ski resorts, which they had owned for several years. When their children grew older and used the property less frequently, they decided to rent it out. However, they faced challenges in deciding whether to manage the rental themselves or hire a management company. They initially tried self-managing but soon realized the workload was overwhelming, especially with maintaining the property, managing guest expectations, handling reviews, maintenance, housekeeping, and complying with local regulations.
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
Exceptional Expertise and 24/7 Service
For the last 18 years, the company’s dynamic team has played a key role in efficiently managing properties. Their extensive market knowledge is a key strength of Winter Park Escapes. The whole team is organized into specialized departments, including the homeowner’s division, onboarding, marketing, guest relations, operations management, maintenance, and housekeeping. This structure allows it to simplify processes and provide the best 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 Repka.
The Sustainability Movement is Here
“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,” says Repka.
Advancing Sustainability
In a world facing increasing environmental challenges, Winter Park Escapes has made notable progress in adopting sustainable initiatives and working towards a greener future. With a strong emphasis on reducing plastic waste and embracing eco-friendly practices, the company is committed to fostering a more sustainable world. It has made substantial strides and, in its ongoing efforts, proudly acknowledges the certifications that reflect its dedication to protecting the environment.
Eliminating Single-Use Plastics
This is a key sustainability initiative for Winter Park Escapes. The company understands the detrimental impact these plastics have on the environment, particularly on marine life and ecosystems. By embracing alternative packaging solutions and promoting reusable alternatives, it actively reduces its reliance on single-use plastics. This effort not only benefits the planet but also encourages a culture of responsible consumption across its properties.
Microplastic-Free Products
Another critical aspect of Winter Park Escapes’ sustainability journey is ensuring that all products used in its properties are free of microplastics. Through careful examination of product ingredients and manufacturing processes, the company has transitioned to offering bath and body products that are free from microplastics. This practice underscores its commitment to providing environmentally friendly options for its guests.
Continuing Green Initiatives
As the company strives to become more environmentally conscious, its commitment to green initiatives remains unwavering. Winter Park Escapes understands the importance of continuous learning and innovation in its sustainability efforts. By exploring new solutions that align with its mission, it seeks to stay at the forefront of sustainable practices, inspiring others and contributing to the broader movement towards sustainability. Through transparent communication and a commitment to growth, it aims to continue this journey for the future of the mountain town it cherishes.
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We currently manage 225 properties with the same dedication and success that started it all. As a trusted name in vacation rental management, we manage everything—from marketing to maintenance—so the property owner can enjoy maximized rental income without the hassle
AI is increasingly making its mark across various industries, and the hospitality sector is no exception. As AI continues to evolve, Winter Park Escapes embraces its potential to enhance marketing strategies, improve data collection, and create more effective communication with both homeowners and potential guests.
Leveraging social media, the company showcases the visual appeal of its properties, highlighting the unique beauty of homes and local attractions. By strategically featuring properties alongside many of its offerings, potential guests are given a compelling reason to visit and stay at these homes. The goal is simple: answer the question, ‘Why travel to Winter Park and stay at your home?’ through impactful marketing campaigns. Also, these efforts are designed to make booking seamless, with direct calls to action, such as QR codes and quick links, allowing potential guests to reserve their stay with ease.
AI plays a crucial role in this process by offering valuable insights into guest behavior and engagement. From identifying the most searched amenities to understanding the demographics most likely to book, data-driven decisions are made to refine marketing efforts. This deeper understanding of guest interactions allows for more targeted and effective promotion of featured properties. Winter Park Escapes also encourages homeowners to engage with its social media platforms, as their feedback and participation are invaluable in strengthening these efforts. With an increased focus on social media outreach, the company appreciates the support of homeowners in amplifying its presence and reach.
Gearing Up for the Next Phase
Looking ahead to the next 18 years, Winter Park Escapes is excited about continuing its journey of growth, excellence, and commitment to its homeowners, guests, and the natural beauty of Winter Park.
Through innovation, an unwavering dedication to sustainability, and a passion for delivering exceptional experiences, it is well-prepared to meet the needs of an evolving travel landscape. 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."
