If you’ve been thinking about buying an investment property in Tampa, you’ve probably already Googled the neighborhoods, watched a few YouTube videos about short-term rentals, and maybe even scrolled Airbnb to see what properties near you are earning. You’re doing your homework and that’s a great sign.
But here’s the question most buyers don’t think to ask: does your real estate agent actually own investment properties themselves?
It’s a question that matters more than you might think.
How I Got Into Real Estate (And Why It Wasn’t About the Commission)
I started in real estate in 2016, and from day one, my passion was investment properties. Specifically, the idea of taking something old, something worn down, and seeing exactly what it could become. The demo process, the design decisions, the transformation, I was obsessed with it.
So I didn’t just help clients buy investment properties. I started buying them myself.
I now own and personally operate three short-term rentals listed on Airbnb and VRBO. And those three properties have taught me more about real estate investing than any course, certification, or market report ever could.
What Running My Own Rentals Has Taught Me
When you manage your own short-term rentals, you learn things fast. You learn how to evaluate whether a property will actually perform, not just look good on paper. You learn what drives bookings, what kills your margins, and what red flags to catch before you’re ever under contract.
I’ve had the tough months. The unexpected repairs at the worst possible time. The “why did I buy this” moments at 2am. And I’ve had the months where everything clicks and you remember exactly why you got into this.
I’ve made mistakes and those have been just as valuable as the wins. Because now, when I’m sitting across from a client who’s looking at their first investment property, I’m not speaking from theory. I’m speaking from experience.
That’s a different kind of guidance than most agents can offer.
The Right Agent Makes a Difference Beyond the Closing Table
There are a lot of great agents in Tampa who can help you find a good deal. But the right agent for an investment property isn’t just someone who can negotiate a strong offer. They’re someone who can help you think through the long game.
Questions like: What will this property realistically earn as a short-term rental in this neighborhood? What’s the carry cost if occupancy dips in the off-season? Is this layout guest-friendly, or will you constantly be fighting bad reviews? What does the HOA actually allow? What renovations will move the needle on your nightly rate versus what’s just cosmetic?
When you work with someone who has been through it, someone who is actively running rentals right now, those conversations become a lot more grounded.
Why Tampa Is Still One of the Best Markets for Short-Term Rentals
Tampa continues to be one of the strongest markets in Florida for short-term rental investors. Between the year-round tourism, the growing population of remote workers, and major events that drive demand, the opportunity here is real. But not every property in every neighborhood is going to perform the same way, and that’s where local knowledge matters.
Whether you’re looking at a property in Seminole Heights, Ybor City, Westchase, or anywhere else in the Tampa Bay area, understanding the micro-market, the rental demand, the guest profile, the competition, is what separates a smart investment from an expensive lesson.
Let’s Talk About Your Investment Goals
If investment real estate has been on your mind, I’d love to have a real conversation about it. Not a sales pitch, just an honest breakdown of what to look for, what to avoid, and whether the numbers make sense for your goals.
I’m Brannen Huckery, a Tampa-based real estate broker and short-term rental investor. Reach out anytime, I’m always happy to talk through it.
813-922-5325
brannen.huckery@theriserealty.com
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