Seasonal rentals play a critical role in Southwest Florida’s dynamic real estate market. For both homeowners and renters, they offer opportunities, challenges, and unique market dynamics that demand attention.
Recently, I had the pleasure of speaking with Jack Breyman, a seasoned expert in this field, on my podcast. With over a decade of experience specializing in seasonal rentals, Jack’s insights shed light on the intricacies of managing these properties, the evolving market, and how to best serve clients.
You can watch the full podcast episode here.
Today, let me give you a glimpse of the takeaways from our interesting conversation!
Jack Breyman’s Real Estate Journey
Jack’s path into real estate was anything but conventional. After college, he realized that the degree he was pursuing wasn’t the right fit. Instead of wasting time in a career he wasn’t passionate about, he made a bold pivot and joined his uncle at Berkshire Hathaway. It was here that he got his first taste of the real estate business.
However, it wasn’t long before Jack found himself wanting more. He moved to Domain Realty, where he gradually carved out his niche in seasonal rentals.
Over the past 12 years, he has become a leader in this space, managing properties from South Naples up to Southwest Cape Coral.
What stood out to me was Jack’s passion and drive to learn, grow, and make a difference in the lives of his clients.
Insights and Market Trends in Florida’s Seasonal Rentals
Seasonal rentals hold a unique position in Southwest Florida’s real estate market. They offer a blend of opportunity and challenge, and few understand this better than Jack. His years in the field have given him a deep knowledge of market shifts, client expectations, and effective strategies.
Seasonal Rentals vs. Resale Market
At first glance, seasonal rentals and property sales may appear vastly different, but there are underlying parallels—particularly in the emotions they evoke.
Jack pointed out that rentals often come with emotional baggage, especially for owners who might have to accept lower returns or face tough financial realities. The rental market, closely tied to property values, is not immune to fluctuations. Rising insurance costs and market softening have also led some owners to grapple with whether to hold onto their properties, even if it means taking a loss or selling at less-than-ideal prices.
Jack’s role is often to guide his clients through these decisions, offering both practical advice and empathy.
Market Trends and Challenges
The market landscape in Southwest Florida has seen an increased supply of rental properties, as exemplified by the current apartment boom, without a corresponding rise in demand. As a result, rental prices have taken a hit.
This trend puts property owners in a difficult position, where they must weigh the cost of keeping their properties occupied at lower rates against the potential of higher vacancies.
Jack explained that the rental market is intrinsically linked with the sales market, meaning that a dip in one often mirrors a dip in the other. This delicate balance requires vigilance and adaptability from both property managers and owners.
It’s a challenging dynamic, but with the right guidance, it’s possible to weather the storm and maintain long-term profitability.
Client Retention and Seasonal Rental Strategies
Jack understands that satisfying clients requires more than just renting out properties—it’s about creating an exceptional experience. By being attentive to their needs, whether it’s finding the best mortgage brokers, recommending contractors, or resolving minor maintenance issues, he ensures that his clients always feel supported.
Satisfied clients are far more likely to return season after season, creating stability and consistency in a market that can sometimes be unpredictable.
Jack also shared that maintaining strong relationships with renters involves being highly responsive. If a client calls about a maintenance issue, his team makes it a priority to resolve it quickly!
Property Management Practices
For Jack, the heart of successful property management is customer service. He is a firm believer that great service begins with small actions, such as changing a smoke detector battery, replacing a light bulb, or addressing minor concerns promptly. These seemingly small tasks can make a big difference in how clients perceive their experience.
Repeat business is key to success in the seasonal rental market. And, when renters feel valued, they are more likely to return in subsequent years!
Shifts in Renter Behavior and Market Dynamics
The market is constantly evolving, and so are renter preferences. Economic factors, insurance hikes, and even past hurricanes have influenced renter behavior.
Jack observed that some seasonal renters who used to book four-month stays are now opting for two months due to financial constraints or other considerations. This shift requires property managers and agents to be adaptable, finding new ways to meet changing client needs without sacrificing occupancy rates.
Another notable trend is the increased demand for flexibility. Jack noted that some renters prefer shorter stays, and this presents both challenges and opportunities. While shorter stays may require more work on the part of property managers, they also open the door to new clients who might have yet to consider seasonal rentals in the past.
Jack’s approach involves understanding these shifts and responding proactively to ensure that both renters and owners benefit.
Adapting to Market Conditions
To stay competitive in the seasonal rental market, adaptability is crucial. Jack emphasized working closely with property owners to adjust rental terms, such as minimum stay requirements or pricing structures. By doing so, you can help them remain flexible, making it easier to keep properties occupied.
Jack’s ability to read market trends and adjust strategies accordingly is one of his key strengths. He knows that the market won’t wait, and proactive adjustments are often necessary to maintain profitability.
Whether it’s dropping a three-month minimum to two months or finding creative solutions to attract renters, Jack’s focus remains on maximizing occupancy and keeping properties rented.
Digitalization and Consumer Education
The rise of digital platforms, like Zillow, Airbnb, and VRBO, has transformed how renters search for and select properties.
As Jack and I discussed, today’s renters are more informed than ever before. They can browse countless listings online, compare prices, and make highly educated decisions about where to rent. This trend has shifted the power dynamic, making it essential for agents and property managers to stay ahead of the curve.
For me, podcasting has been an incredible tool for educating and engaging with my audience as well. By working with a professional real estate podcast production company, I’ve been able to create high-quality content that resonates with my listeners.
It’s a strategy I recommend for agents looking to elevate their industry presence and share their expertise.
Subscribe to the 239 Real Estate Roundtable Podcast to Hear More Profound Stories and Insights from Industry Experts!
Jack’s insights offer a window into the evolving world of seasonal rentals. His experience, compassion, and dedication to serving clients make him a standout professional.
If you found the information I shared here valuable, I invite you to subscribe to the 239 Real Estate Roundtable Podcast. Each episode brings expert knowledge, industry trends, and real stories impacting homeowners, renters, and real estate professionals.
And, if you’re ready to embark on your real estate journey in Southwest Florida, contact me today to explore your options and benefit from my expertise. Let’s make your investment a success!
