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Inspiring Conversations with Andrew Greenstein of Orlando Area Luxury Rentals

Today we’d like to introduce you to Andrew Greenstein.

Hi Andrew, thanks for joining us today. We’d love for you to start by introducing yourself.
I’ve always been told that I’m a big kid (well, except when I was a little kid!).

I worked 125 hours per week from age 21-28 to retire young (in 2001)—cramming 20+ years of work into just 6.5.

But…..

I designed my own home for myself and my family to have a ball pit room filled w/ 23,000 colorful, air-filled balls, an indoor slide…carousel horse rides..and more.

We love to travel around the globe and were sometimes on vacation over 100 nights per year…so I decided around to rent out our own home (the now famous “Ever After Estate”) featured on HGTV’s “Most Outrageous Homes in America” whenever we traveled/vacationed.

That was around 2010— and by 2012 it was so in-demand that I decided to buy another home and remodel it into what is now known as The Sweet Escape Mansion (which Travel & Leisure Magazine called “….more fun than Disney itself!” We designed the world’s only remaining ice cream cone pool there and made the hot tub the literal ‘cherry on top!’ There’s even a splash park, a giant chocolate syrup bottle spraying the “chocolate waterslide!,” and a custom-built…candy-themed golf course.

As Sweet Escape became busier…and busier…my 2 kids were getting older…and older.. They were practically “tweens” and we were always talking about how cool it would be to have a “game-themed house.” Sometimes at dinner, we’d throw around fun ideas and write them in notepads on our devices. I realized that I didn’t want my kids to see me have ideas or dreams and throw them to the side. I wanted them to see that you can have a dream and make it into a reality.

So, as a family– we designed The Great Escape Lakeside. The game-themed house w/ the world’s first residential laser maze, a playable escape room, and a Guiness Book of World Records making gigantic word search wall.

THAT was the game changer (pun intended).

In January of 2018, a BuzzFeed “BringME” video about Great Escape Lakeside went mega viral. It accumulated 90 million social media impressions rather quickly and local and national news networks started picking up the story. In about 2 days, we sold out every night for a couple of YEARS. Our servers crashed. We couldn’t handle all the calls. At one point, we had our teenagers helping answer the lines…

It was INSANE!!!!

With the demand so high, we decided to announce that we were building another, The Great Escape Parkside. Before we even bought land for it, people were giving us down payments for family reunions, corporate retreats, and even weddings. The “fan” response was overwhelming….and Parkside went on to become just as popular as Lakeside.

Later on, a local homeowner hired me to re-model and re-theme his beautiful but ordinary vacation rental into The Lake Louisa Chateau, the world’s first sports-themed vacation mansion. That one opened in late 2020 and we helped bring his bookings up from about 20 nights per year to over 250 pretty much instantly!

We are blessed that so many people want to come stay and play in these unique “experience” homes. I am touched when I hear that people watch our online videos and plan their stay for 1-2 years before finally coming–and it’s so exciting when I get to witness the looks on their faces when they first arrive.

Sure, like any business– It has its issues and challenges from time to time–but my decades of experience in multiple businesses combined with the skills of my awesome wife, family, and work team—make it my life’s favorite endeavor.

We all face challenges, but looking back would you describe it as a relatively smooth road?
We built, decorated, and opened Great Escape Parkside in just 6.5 months from the moment we broke ground. That’s it. Yes, just 6.5 months– Most builders can’t even get an empty house shell done in that time– We had it built, decorated, laser mazes & escape rooms made…. 14 artists tattooing the walls w/ their intricately detailed themed murals, and more! Along the way, we had to deal w/ lost paperwork issues, vendors ripping us off, local hooligans sneaking in and cutting wires before drywall went up, windows mis-measured, and so many other construction headaches…and that’s just one house, one project….

There’s plenty more to overcome month to month to keep everything running smoothly for 15,000+ visitors per year!

Thanks for sharing that. So, maybe next you can tell us a bit more about your business?
Uniquely themed vacation estates on acreage that sleep at least 43 people each— and offer things NO ONE else does!

We’d love to hear about any fond memories you have from when you were growing up?
Non-specific– but I miss waking up and watching TV and having no phones and no responsibility.

Contact Info:

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