Today we’d like to introduce you to Austin Hair.
Hi Austin, we’d love for you to start by introducing yourself.
I’ve always been drawn to creating experiences that bring people together. My background as a world champion wakeboarder and American Ninja Warrior finalist taught me how to set ambitious goals, stay disciplined, and think creatively — lessons that carried over when I transitioned into real estate.
What started as a single investment quickly turned into a passion for building unique, large-group vacation rentals designed for connection and nostalgia. Over time, I acquired and expanded several iconic properties — including The Great Escape Lakeside and The Great Escape Parkside — transforming them into immersive “game-themed” estates that feel like private theme parks.
Today, my focus is on growing a portfolio of high-yield, experiential short-term rentals that redefine what a vacation home can be — places where families, friends, and groups can reconnect, celebrate, and create memories that last a lifetime.
Would you say it’s been a smooth road, and if not what are some of the biggest challenges you’ve faced along the way?
It’s definitely not been a smooth road. One of the biggest challenges has been financing — especially in today’s lending environment. Traditional banks aren’t built for creative projects like these. When you’re buying multi-million-dollar vacation homes that look more like private resorts than standard rentals, lenders don’t always know how to underwrite them.
Every deal has required a different puzzle to solve — between appraisals that undervalue experiential properties, short-term rental restrictions that spook underwriters, and fluctuating interest rates that make cash flow tight. I’ve had to get creative — combining DSCR loans, seller financing, and even pledging securities to make some deals work.
But in a way, that’s been the best part of the journey. Each challenge forced me to think differently, build stronger relationships, and find lenders who actually understand this new asset class. The process has made me sharper and more resilient — and it’s why I believe experiential real estate will keep outperforming as people seek connection and memory-driven travel.
As you know, we’re big fans of Orlando Area Luxury Rentals. For our readers who might not be as familiar what can you tell them about the brand?
At Orlando Area Luxury Rentals, we specialize in creating one-of-a-kind, large-group vacation experiences that blend luxury, nostalgia, and play. Our flagship estates — The Great Escape Lakeside and The Great Escape Parkside — are not just vacation homes; they’re immersive, game-themed destinations that feel like private resorts. Each property is filled with interactive design elements, from life-size board games to escape rooms and themed theaters, allowing guests to reconnect through creativity and fun.
What sets us apart is our focus on storytelling and emotion. We don’t just rent houses — we design experiences that help families, friends, and teams feel like kids again. Every detail is intentional, from the layout of shared spaces to the way lighting, sound, and design transport guests into another world.
We’re proud to continue the legacy of these iconic “Great Escape” properties while expanding into new experiential destinations that redefine what short-term rentals can be. Our goal is to build a portfolio of world-class, memory-driven vacation homes that inspire connection — because we believe the best trips aren’t just about where you stay, but what you feel while you’re there.
Before we go, is there anything else you can share with us?
You can follow our journey on instagram: OrlandoAreaLuxuryRentals
Pricing:
- $1600/night
Contact Info:
- Website: http://orlandoarealuxuryrentals.com
- Instagram: https://www.instagram.com/orlandoarealuxuryrentals/
- Facebook: https://www.facebook.com/greatescapelakeside
Image Credits
austin hair
