Orlando Vacation Homes · Short-Term Rentals
More Than Real Estate
25+ years in real estate. A lifetime built on relationships.
Brad Rogers · Florida Real Estate Professional
The Practice
A specialist in Orlando's vacation-home market
For more than 25 years, Brad has worked in real estate. Today, his focus is the vacation-home and short-term-rental market surrounding Walt Disney World — one of the most unique investment landscapes in the country.
Buying a vacation rental isn't like buying a typical home. The numbers have to work, the community has to allow it, and the property has to appeal to guests — not just owners. Brad walks his clients through all of it.
The relationship doesn't end at closing.
Brad's clients gain access to a network he has built over decades — property managers, contractors, handymen, maintenance companies and decorators who know the vacation-rental market inside and out.
Long after the keys change hands, Brad stays in his clients' corner — because to him, a closing is the beginning of the relationship, not the end of it.
The Personal Story
A Friendship That Started in Fifth Grade
Brad grew up in Auburndale, Florida — a small town where friendships tend to last. His oldest friendship began in fifth grade, with a classmate named Tracy McGrady.
Long before Tracy became an NBA star and a Basketball Hall of Famer, he was simply Brad's best friend. And as Tracy's career developed, Brad was there — serving as his personal assistant and business partner, while remaining, above all, his best friend.
It's the kind of loyalty you can't manufacture. Decades of trust, showing up, and treating people well — the same qualities Brad brings to every client relationship.
Auburndale, Florida — where a fifth-grade friendship began
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On set during Tracy's NBA years
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Celebrating Tracy's Hall of Fame honor
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Orlando Magic Hall of Fame — three generations of friendship
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Two families, decades of loyalty
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Backstage with Uncle Kenny and family
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A quiet moment before the show
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Kenny Rogers with the Rogers kids — the early years
ExpandThe Family Story
Lessons from an uncle named Kenny Rogers
Brad's uncle was Kenny Rogers. And while the world knew Kenny for his music, what left the deepest impression on Brad was his uncle's entrepreneurial and creative side — the way he saw possibility where others didn't.
Brad still remembers his uncle's property near Athens, Georgia — roughly 800 acres — and watching it transform over time into an estate and golf-course setting. As Brad recalls it, seeing what that land became planted something in him: a fascination with real estate, and with recognizing the potential inside a property before the rest of the world catches on.
That instinct — seeing what a property could be — still shapes how Brad serves his clients today.
Why It Matters
"Real estate is ultimately a relationship business. Trust, loyalty and treating people well matter to me—and they mattered long before I ever sold a house."
— Brad Rogers
What Clients Say
Google Reviews About Brad
"Brad Rogers and his team were excellent in helping me find the right home and closing the deal. Brad was incredibly responsive at each step of the way and guided me admirably. If you are looking for short term rentals in Disney/Universal area, I highly recommend Brad and Holiday Realty."
Ramesh Narasimhan
Google Review
"It was a pleasure to work with Brad as a realtor. He is very knowledgeable about the area, and the process. After a brief call he knew exactly what I was looking for, and provided only high quality leads. He was very responsive, and I felt that he went above and beyond to help me find a suitable property."
Chris Antaris
Google Review
"Brad is a great realtor — knows the market very well. He is always quick to respond and always helpful in the purchasing process. Thanks for everything!"
Kim Smiga
Google Review
Work With Brad
Whether you're buying or selling an Orlando vacation home or exploring a short-term-rental investment near Disney, Brad would love to hear your story.
Prefer the contact form? Send an inquiry.