Updated on May 2, 2023
When Francine and Kevin Rollock of Calgary, Canada, bought a condo on the Dominican Republic’s northern coast, they envisioned a retirement filled with volunteer work and basking in the sun.
The couple both had long careers in the oil and gas industry in Calgary, a city with long, freezing, and snowy winters. They wanted to retire to a warmer climate and had heard good things about the Dominican Republic.
“We had never been here before,” Francine said. “We just heard that the Dominicans were really nice people and that it was affordable, too.”
Owning a vacation rental in retirement
In 2006, they bought a condo in the resort town of Cabarete, known for its beautiful beaches and bay protected by a coral reef.
For the first three years, they took two vacations to the Caribbean nation to stay in their condo and met some of their neighbors.
In a remarkable coincidence, the Rollocks found out from a travel blog that two other homeowners in the condominium, known as the Victorian Cabarete, also lived in Calgary.
They contacted the other homeowners and later gathered together in Calgary to get to know one another over dinner.
Then, in 2009, the Rollocks decided that the time had come to retire and live fulltime in the Dominican Republic. By then, they had gotten to know several of the other expats who lived in the complex. Many of them were snowbirds, living in their condos only during winter months.
Not long after the Rollocks started living there full time, some of the snowbirds began asking if the couple would manage their condos and rent them out as vacation rentals when the owners weren’t using them.
By the time Francine and Kevin had settled into their new home, they were already managing four other condos.
Francine and Kevin quickly discovered that they loved hosting guests. “We were meeting a lot of people coming from everywhere in the world,” Francine said. “So, it was really interesting, and managing the properties put us in touch with more Dominicans.”
To manage the properties, the couple had to interact with vendors and service providers and eventually hire employees. The interaction helped the couple learn Spanish faster and learn more about the culture.
“We discovered more and more that it is very important to be part of their family. The Dominicans have a great sense of hospitality, and if you limit yourself to a boss-employee interaction, it doesn’t make things easy,” Francine said.
For their first Christmas in the Dominican Republic, one of their housekeepers invited them to her family’s holiday celebration attended by her eight children and 35 grandchildren.
“After the meal, we ended up dancing the merengue and the bachata, and we came home at 4 o’clock in the morning. That was really pleasant. It’s not like we talked a lot because at the time our Spanish was very basic, but just being here, being immersed in their life was a very amazing experience,” Francine said.
Not only was the culture and the language new to them but so was vacation rental management. Francine said the couple learned how to manage properties simply from doing so. Starting out on a small scale with just four properties helped to soften the learning curve.
Then, during the condominium’s annual meeting that year, Kevin was elected to the board of directors. His more prominent name in the community prompted more owners to ask the Rollocks to manage their properties at the Victorian Cabarete.
“As he became more known, people approached us more and more, knowing they could trust us and their condo was in good hands,” Francine said.
As their portfolio grew, they named their business Quisqueya Management. Quisqueya means “mother of lands” in the language of the Taino, the indigenous people of the Caribbean who largely died out from European disease after Europeans came to the Americas. The Taino called the Dominican island Quisqueya.
Quisqueya Management now manages 30 condos and employs seven Dominicans as housekeepers, office staff, and maintenance specialists. The homes are rented out on a daily, weekly, or month basis depending on the owners’ preferences and are listed on multiple listing sites. A few of the condos are rented long-term. A handful of owners didn’t want to rent out their condos as vacation rentals and just contracted with Quisqueya Management for cleaning and maintenance services.
“It’s really kind of like juggling or being the conductor of an orchestra,” Francine said.
As their company grew, she and Kevin wanted to professionalize it. They were dissatisfied with their website and began searching for companies that could improve it. During their research, they found Futurestay, a vacation rental management solutions platform for independent managers, and after learning about their services, decided to give it a try.
Futurestay not only provided them with a polished, user-friendly site, but they took the chaos out of keeping up with multiple booking sites with an automated system for reservations with instance notifications, Francine said. The platform also allowed the Rollocks to begin accepting credit cards from guests, an option that had been too expensive to offer on their own.
Explore Rent Responsibly Hosting and Management Resources
“In no time, we had a functioning website, our calendars were synchronized, and everything became a lot easier,” Francine said. “Four years later, we’re still very happy to work with them.”
The automation decreased the workload on Francine and Kevin. The couple now has more time to enrich the experience of their guests by organizing boat trips where they can see the local wildlife and try Dominican food like sancocho, a stew made of several kinds of meat and root vegetables.
Opening a vacation rental management company in a foreign country brings unique challenges: different laws, customs, cultures, and language.
Francine said it’s important to respect the culture and learn the language. It makes it easier to communicate with employees, work with contractors, and find out information for guests to make their stay more enjoyable. The couple treats their employees like family members, and they are rewarded with low employee turnover. For instance, the housekeeper who invited them to her home on their first Christmas in the Dominican Republic still works at the company.
The Rollocks’ life involves a lot more work than they had envisioned for their retirement, but it has been a satisfying and rewarding career reinvention, Francine said.
“We are very happy here,” she said. “We have a nice life. We love to have so many friends and families in the Dominican Republic. We hear that very often from our Dominican friends: You know, we are your family.”
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