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Military to Millions

The Howard’s journey from the front lines to luxury vacation rentals

Article by Savannah Vasquez

Photography by Shanna Magson -

Originally published in Destin City Lifestyle

If ever there was a Destin power couple, Jonathan and Rizzete Howard would be it. Jonathan is a serial entrepreneur and the head broker for AvantStay® in the state of Florida and Rizzete manages all the administration for the couple’s many businesses. However, if you ask the Howards, they will tell you they did not set out to build eight-figure businesses or even to work in real estate; the calling just found them.  

“I tell people all the time that I accidentally got into real estate,” Jon laughed. “Of course, they don’t believe me, but it all started with one little condo we named Destin Charms.” 

Let’s rewind a bit. Jon and Rizz met in 2008 while serving in the US Air Force. The pair do not share their story often, as their military jobs were quite gruesome - her being a mortician and him on the front lines in Combat Control and Special Operations - but it was the common bond of living through trauma that has made them a force to be reckoned with.  

“I knew she was the one after dating her for four months,” Jon said. “I was getting ready to cross-train into Special Ops, but I could not stand being away from her. We had a little courthouse wedding in 2008.” 

Military life was tough as the couple were often separated for extended periods of time and both served during the Middle East wars. The pair saw friends killed in action and had to live through countless funerals and war-front tragedies. But military life was what the Howards knew, it was what made them, it was what kept them close.  

“What we saw in the military was a really eye-opening experience,” Jon said. “But she and I being together, we didn’t have to talk about it; we knew. Because we could lose each other at any given moment, we became really close.”  

When Jon reenlisted for the last time in 2014, he used his bonus to buy a condo on the Destin Harbor. Together Rizz and Jon renovated the place and moved into it. A friend suggested renting their condo on VRBO while they were gone for the summer of 2015.

“We had designed our condo for our home, so it was really nice. I put it up on VRBO just to see what happened,” Jon said. “Three days later it was booked out for $18,000 for just six weeks! I remember thinking, ‘What did I just stumble upon?’” 

Over the next three years, Jon finished his military career, all the while renting out his condo and slowly adding more properties to his now growing vacation rental business. But moving on from military careers into the civilian world was daunting. 

“It’s kind of scary when you’re getting out,” Jon said. “I found myself asking, ‘What if I don’t adjust well, what if I’m damaged goods?’ I never thought I would do well on the outside because it’s hard to explain what you do and see as an operator in the military.”

But it’s no secret that the Destin community supports veterans. As so many residents are brought to the Florida panhandle area because of the military, there are many lines of support for veterans in Destin.  

“A lot of people would find out who I was and find out that I was a veteran and would want to help me with business,” Jon said. “Destin was a very welcoming place.” 

The couple had another thing going for them; the ability to thrive under pressure and to work together for a common goal. 

“Like any other couple it’s hard to work with your partner because you have to keep it professional and keep your emotions out of it,” Rizz said. "I’m very good at reading people and he’s very good at giving the benefit of the doubt so we balance each other out.” 

Jon echoed that sentiment, saying that while he is the face of the business, Rizz handles everything behind the scenes.  

“A lot of times spouses can’t work together but she and I work so well together because she knows my weaknesses and my strengths,” Jon said. “I’m like a sledgehammer, I set the temperature and tempo and she is the attention to detail and the administrative side, making sure all our ducks are in a row.” 

Jon decided to go to law school in 2018 with the vision to support military veterans like himself. Just as he completed his first year in Naples, the rental business and home sales were growing rapidly, so with 20 rental properties, Jon returned to Destin full-time from Naples to help Rizz run Destin Charms, later renamed Florida Charms Vacation Rentals and Realty in 2019.  

“From that point on the business doubled every quarter, just growing and growing,” Jon said. “We started getting offers to sell the business from private equity companies in 2020, but I didn’t really like these other companies, they were big corporations. The big appeal for my company was that the homeowners only dealt with me, and I had developed good relationships with them and never wanted to hand them off to a bad company.”

In March of 2022, the Howards received an offer they could not turn down. AvantStay® not only offered the right price, but also made sure every employee was taken care of and kept Jon on as the broker for the state of Florida.  

“To get recognized by a nationally ranked company like AvantStay® was really awesome,” Jon said. “They wanted a real estate broker that was vacation rental focused not sales focused. I didn’t care about selling every house on 30A, I just sold what I was going to manage.” 

With the weight of managing the company behind them, the Howards say a new chapter has opened for them, one that gives them more time for their passions and more time together.  

For Jon, he plans to dive deeper into his veteran advocacy projects.  

“One of my friends I was on the team with started First There Foundation,” Jon said. “The whole idea is to raise money for veterans to get mental health treatments without having to go through the VA. We also put on retreats with mental health professionals. It's things like this that give me purpose.” 

As for Rizz, she plans to start her doctorate in behavioral sciences and traumatology. And of course, the couple has plans to travel and enjoy their newfound time together.  

"We love helping people,” Rizz said. “We don’t view what we’ve accomplished as a success, we just did what we had to do when the time was good, we took the opportunities and I’m glad we did.”

“It’s kind of scary when you’re getting out. It’s hard to explain what you do and see as an operator in the military.” - Jon