The Everyday Realities of a Short-Term Rental Property Manager

Managing short-term rental properties might seem like a straightforward venture — list your property, wait for bookings, and collect your earnings. But Derek DeCesere, founder of Sand Stays, quickly learned that the reality is far more nuanced. His journey, which began with just a few properties in Maine and now encompasses over 100, offers valuable insights into what it truly takes to thrive in this competitive industry.

In the latest installment of the Hostaway Webinar Series, Derek sat down with Hostaway CEO Marcus Rader to reflect on his experience and share the lessons he’s learned along the way. Here’s how Derek navigates the everyday challenges of managing a short-term rental business — and what others in the industry can take away from his approach.

Finding The Right Business Model

Every successful business begins with a model that fits its long-term goals. Derek’s journey in short-term rentals began with a rental arbitrage approach, where he would rent properties and then sublet them on platforms like Airbnb. It’s a model that can bring in significant profits — but it’s also fraught with risk.

“Lease arbitrage can be very profitable, but it comes with volatility,” Derek explained during the webinar. “You’re at the mercy of rising rents, market competition and other factors outside your control.” After weighing the pros and cons, Derek shifted his focus to property management, where he oversees properties on behalf of owners rather than leasing them outright.

This pivot allowed Derek to build a more sustainable business. This strategic move helped him focus more on long-term success rather than getting sidetracked by short-term ups and downs in the market. This transition reflects a key lesson for aspiring managers: the importance of choosing a business model that suits your comfort with risk and long-term aspirations.

Understanding Your Guests

At the core of Derek’s strategy is a deep understanding of the people who stay in his properties. Early in his career, he realized that different guests have very different needs. Some are families looking for a kid-friendly beach vacation, while others are solo travelers exploring Maine’s cultural landmarks or attending local events.

“Recognizing these differences helps us create a more personalized experience for each type of guest,” Derek noted. For example, while families may prioritize spacious homes with safe outdoor spaces for children, event-goers might be more interested in location and convenience. In Maine, where Derek operates, tourism can range from beach vacationers to Stephen King fans seeking literary landmarks. Catering to these varied preferences has been key to his success.

This deep understanding of guest needs also informs the amenities Derek offers. It’s not just about providing a place to sleep — it’s about creating an experience that matches guests' expectations. And as Derek has learned, tailoring the experience can lead to better reviews, repeat business and long-term success.

Building Strong Relationships Through Direct Bookings

For Derek, cultivating strong relationships with guests is critical to the long-term success of his business. One of the most effective ways he does this is by prioritizing direct bookings, bypassing third-party platforms like Airbnb and Booking.com.

“Direct bookings are crucial for us,” Derek shared. “Not only do we save on platform fees, but we also get the opportunity to build stronger relationships with our guests. We can communicate with them directly and encourage repeat stays.”

Using tools like StayFi, which captures guest emails through Wi-Fi logins, Derek has been able to gather valuable guest information. This has allowed him to market directly to past guests with special offers and incentives, encouraging loyalty and driving future business without the fees that come with third-party platforms.

The takeaway for other property managers? Direct bookings not only boost your bottom line, they also give you greater control over guest relationships, enabling you to create a more personalized experience that leads to repeat business.

Managing Relationships With Guests and Owners

Managing short-term rentals means striking a delicate balance between the needs of guests and property owners. For Derek, this is one of the most challenging aspects of the job. “It’s a delicate balance. You need to meet guest expectations and provide excellent service, but at the same time, you have to manage the property owner’s expectations,” he said during the webinar.

Guests, especially those staying in luxury properties, often have high expectations for amenities and services. If these aren’t met, it can negatively impact reviews and future bookings. On the other hand, property owners can be demanding in their own right, sometimes expecting more from the manager than is realistic or financially viable.

Derek emphasized the importance of clear communication from the start. “You need to set the right expectations, both with guests and with property owners,” he said. For guests, this might mean ensuring that listings accurately reflect what is offered. For owners, it’s about setting boundaries and being transparent about what can and can’t be done. In some cases, walking away from a difficult owner is the best way to protect your business.

Adapting to Seasonality: Maximizing Bookings Year-Round

Seasonality is an inherent challenge in the short-term rental business, particularly in regions like Maine, where summer tourism is at its peak. However, Derek has found creative ways to maximize bookings even during the quieter months. “While the peak season might end in early September, we’ve found that September and even early October are still great months,” he shared.

Understanding these “shoulder seasons” as they’re known in the industry, is key to keeping properties booked year-round. Derek has discovered that many travelers prefer quieter, off-peak vacations and he adjusts his marketing strategies to appeal to them. Promoting properties as ideal for remote work or long-term stays can attract a different type of guests and help smooth out seasonal ebbs and flows.

Leveraging Technology to Streamline Operations

One of the most significant factors contributing to Derek’s success is his use of technology to streamline operations. Managing over 100 properties is no small feat and automations have been critical in making that possible. Derek credits Hostaway, an all-in-one property management platform, for helping him keep his business running smoothly.

“Hostaway has been a game-changer for us,” Derek noted. “Managing bookings across multiple platforms would be impossible without it. The ability to sync everything in one place saves us hours every day.” Hostaway offers a range of features, from channel management to guest communication automation and even dynamic pricing tools that help managers adjust rates based on demand and seasonality.

Automation has freed up time for Derek to focus on higher-level tasks like guest experience and business growth, rather than getting bogged down in administrative work.

Data-Driven Decisions are Key to Continuous Improvement

In addition to automation, Derek relies heavily on data to make informed decisions about his properties. Data tools provided by Hostaway give him valuable insights into booking trends, guest demographics and property performance. “Data is your best friend in this business,” Derek emphasized. “It allows us to adjust our pricing, understand guest behavior and make improvements where necessary.”

For instance, by analyzing booking patterns, Derek can identify periods where demand is lower and adjust his marketing or pricing strategies accordingly. These data-driven adjustments have helped Derek maintain steady bookings and maximize revenue.

Thriving in a Competitive Industry

Derek’s story shows that managing short-term rentals is far more than just listing properties — it’s about balancing guest and owner relationships, adapting to market trends and using technology and data to stay competitive. The business of short-term rentals is demanding, but as Derek’s journey shows with the right approach, it can also be incredibly rewarding.

His key to success? Staying flexible, continuously improving operations and understanding that the needs of both guests and property owners are at the heart of the business. For property managers hoping to thrive in this industry, Derek’s experience offers a clear roadmap: leverage technology, build strong relationships and never stop learning.