Redefining Legacy Management with a Hospitality Mindset 

For Dennis Levy, success in the timeshare industry isn’t about selling weeks—it’s about serving people. As Vice President of Operations at FantasyWorld Management Services, Levy has transformed a legacy resort into a financially stable, owner-focused destination by leading with a hospitality-first approach and championing board member education across the industry. 

Originally developed in the 1980s, FantasyWorld is a mixed-use property located in Kissimmee near Disney. Two thirds of the resort consist of an owner-controlled legacy timeshare, however the property also includes a timeshare vacation club, short-term rentals, long-term rentals, and even a couple of owner-occupants. Facing the same pressures as many legacy resorts–aging infrastructure, owner delinquencies, and strained relationships with third-party management companies–in 2017, the timeshare’s board decided it had to do something different. 

“They didn’t want to be in the timeshare sales business anymore, but they had to remain a timeshare,” Levy recalls. “Without active sales, they knew they had to make up for lost maintenance fee revenue by maximizing rental revenues. They terminated their relationship with their management company, hired a hospitality-focused team, and began running the resort like a hotel.” 

Levy was a natural fit for this transition. After earning his hospitality degree from UCF’s Rosen College of Hospitality Management, the 2009 recession initially pushed him into real estate. He never lost touch with his former professor, Dr. Jeff Weinland—who happened to be president of the timeshare board at FantasyWorld. Dr. Weinland became both a mentor and business partner as Levy added revenue auditing services to his business interests. As Board president, Dr. Weinland knew that for the new management concept to succeed, he needed people with unique skills and that Levy was one of those people. Eventually, the very persuasive Dr. Weinland was able to convince Levy to join FantasyWorld. “Jeff loved FantasyWorld like his own child, and he wanted it to succeed and to create lasting memories for the families it served. He told me he needed me, and I decided to trust him.”  

The move was more than operational. It was ideological. “We don’t actively sell timeshare anymore,” Levy explains. “The only way to buy is through a third party. But what we do exceptionally well is hospitality. We deliver the services of a resort with the privacy and independence of an Airbnb. Historically, timeshare management firms were very good at HOA and condo needs like governance and compliance but lacked hotel style rental expertise. Often, excess timeshare inventory was dumped into the OTAs at a rate designed to put heads in beds. That attracts lower quality rental guests and puts a lot of wear and tear on rooms, fixtures, and amenities. In addition to elevating the guest experience, we use tried and true hotel management techniques like loyalty programs and revenue and yield management to maximize rental income. Everyone knows the Golden Rule, but we use the Platinum Rule instead: Treat others the way they want to be treated. It’s an ideal philosophy for hospitality; you give people what they want. We give our timeshare owners a beautifully maintained resort for a reasonable maintenance fee by giving rental guests a great experience for a fair price.” It’s a strategy that works. With an impressive amenities package and programs offering flexibility and fair exit options, Fantasy World has maintained high owner satisfaction without adding financial strain. “We’ve had exit programs in place since 2014,” says Levy. “They’re designed so that when one owner leaves, the others aren’t penalized. Owners can leave immediately with a fee or speed up usage. It’s about fairness and financial integrity.” 

His commitment to informed governance extends beyond his resort. Levy has been a longtime supporter of the Timeshare Board Members Association (TBMA) and now proudly supports ARDA, which recently began stewarding TBMA’s operations. “TBMA is essential,” he says. “It’s where board members learn how to protect their resorts from mismanagement. When ARDA stepped in to save TBMA, I felt personally obligated to support them. I became a VIP ARDA member because it was the right thing to do.” 

ARDA also offers him a chance to network with larger hospitality players. “As we look beyond 2030, we may need partnerships to keep the property thriving. ARDA brings together the type of companies we might work with in the future.” 

While Levy’s professional story is one of strategic transformation, his personal life offers a surprising twist: he’s a passionate glassblower. Introduced to the art form as a child, he rediscovered it during the pandemic and now helps run a local studio, even teaching classes and assisting on major commissions. “It’s a team sport and a creative outlet,” he says. “It gives me balance. When I’m blowing glass, I can’t think about anything else. It’s the best kind of therapy.” 

Levy’s passion for travel mirrors his work philosophy—immersive, thoughtful, and rooted in authentic connection. He prefers Airbnbs to hotels, savoring the opportunity to “feel like a local.” He often travels to visit his globe-trotting parents, who spend winters abroad, and enjoys group tours for their social element. “There’s a special magic in shared travel,” he says. “Just like in timeshare, people form bonds that last a lifetime.” 

From revitalizing a legacy resort to mentoring fellow property managers and board members, Dennis Levy is reimagining what success looks like in the timeshare industry. And whether he’s helping guests make memories in Orlando or shaping molten glass into art, his mission remains the same: serve with heart, and lead with integrity.