Vacation Rental Pioneer Awards Honor Heather Bayer, Jeanne Dailey, and Carole Sharoff

At the Vacation Rental Women’s Summit, recently held at the Ritz-Carlton in New Orleans, Vacation Rental Pioneer Awards were presented to three outstanding women for the essential and transformative roles each played in building the vacation rental industry into what it is today: Heather Bayer of CottageLINK Rental Management in Ontario, Canada, Jeanne Dailey of Newman-Dailey Resort Properties in Destin, Florida, and Carole Sharoff of Atlantic Vacation Homes in Cape Ann, Massachusetts.

When each of these women started their businesses, less than 10 percent of travelers were choosing vacation rentals for accommodations. As the vacation rental industry grew, each of these businesswomen excelled in managing change, building successful businesses, and working with their destinations and in the industry as a whole to provide vacation rental accommodations that will exist for generations to come. 

“There are just simply some women in our industry who led the way, and we have all benefitted from it. It wasn’t hard to determine which women would receive the Vacation Rental Pioneer Award,” said Amy Hinote, founder of VRM Intel and the Vacation Rental Women’s Summit. “We owe Heather, Carole, and Jeanne an enormous debt of gratitude for all they’ve done over the decades to build their destinations, to professionalize the industry, to embrace others, and to set an example.”

 

HEATHER BAYER, CottageLINK Rental Management and Vacation Rental Success Podcast, Ontario, Canada

Heather Bayer was indoctrinated into the life of hospitality at a very young age, almost as if she had it in her blood. As a child of an Air Force family (her Canadian father and British mother met during World War II), hospitality was a part of life, growing up moving every few years. Now married to an Air Force officer herself, Heather and her husband Phil put down roots by purchasing a pub in Norfolk, England. The success of the pub soon led to the purchase of a small hotel and Heather’s first foray into the world of accommodation.

The person whom we know today as a pioneer in the vacation rental industry was ignited in August 1997 when her family traveled to Canada for a family wedding and rented a self-catering cottage on a lake in Ontario. The stay had ups and downs, and she decided that having a customer-focused mindset would make these rentals much more successful. Six months later, she formed her first rental company Clearwater Holidays, and her inventory rapidly grew to 40 properties as word got out. Heather discovered quickly that she needed to raise property standards and improve education. With her husband’s impending retirement from the Air Force, and as internet bookings began to boom, they purchased three properties of their own in Ontario. 

In 2004, a partnership was created with the owner of another Ontario-based online cottage catalog. With a continued focus on new owner acquisition and education, inventory grew to over 100 properties, and the need for an educational resource was born. Heather’s website cottageblogger.com was launched in 2006 to help the company’s homeowners improve the quality of their rentals; and in 2014, Heather created a podcast to help other vacation rental business owners.

Today with over 1 million downloads, the Vacation Rental Success podcast has been publishing episodes every Wednesday for nearly eight years. Heather’s journey has had many twists, turns, successes, and failures, but at her core, she has always had a passion to share her love for hospitality, kindness, and friendship with others—making her the perfect definition of a vacation rental pioneer.

“Heather has completely dominated in terms of making sure that our industry gets more professionalized,” said Hinote. “She brings people who are new to the industry into the fold, educates them, and gives them a launching pad to make their businesses. There are a lot of businesses that are still here today because of what Heather has done.”

 

 

JEANNE DAILEY, Newman-Dailey Resort Properties, Destin, Florida

In 1983, after graduating from East Carolina University, Jeanne Dailey’s college roommate took a job in Destin, a fast-growing beach community on the Gulf Coast of Florida. Her roommate’s excitement about moving to Destin was contagious, so Jeanne set up some job interviews of her own. A local real estate agent named Randy Newman happened to be in the process of launching a new real estate and resort property management company, and he hired her immediately. 

Once she arrived in Destin, she obtained her real estate license and her broker’s license, and she started selling vacation homes and condos and managing homeowners associations. It wasn’t long before Jeanne also assumed the role of developing the vacation rental program, a business that would become her passion for the next four decades. Recognizing genius determination, Dr. Randy Newman partnered with her in 1985 to launch Newman-Dailey Resort Properties. Taking over the company in 1988, Jeanne decided to keep the Newman-Dailey name because in three short years it had already become one of the area’s most notable brands. 

As Destin grew to become one of the premier beach destinations in the world, Jeanne grew along with it and became a force of nature on the Gulf Coast. From serving as the first woman to be inducted into the Destin Rotary Club to her advocacy for vacation rentals to her passion for beach nourishment, Jeanne is a true pioneer and has been breaking barriers in the community since she made Destin her home. 

Jeanne Dailey has built a company that values integrity and ethics, where team members are treated like family, and where everyone works together to achieve common goals. As a testament to Jeanne’s leadership, Newman-Dailey Resort Properties constantly earned accolades like Best Places to Work by Florida Trend Magazine as well as Best Management Company on the Emerald Coast by the readers of Emerald Coast Magazine. As founder and CEO of Newman-Dailey Resort Properties, Jeanne has shown us each day that anything’s possible. This year, Newman-Dailey will celebrate 37 years of helping guests, homeowners, and employees make their dreams a reality at the beach. With signature grace and poise. Jeanne Dailey has been a consistent example of passion, drive, innovation, and leadership for thousands of women in the vacation rental industry.

“I have watched Jeanne Dailey my entire career since I started at an ad agency before I was even in vacation rentals,” said Hinote. “I’m not ashamed to admit that I copied many of her marketing concepts. She is the star—the standard that we all want to be on the Gulf Coast. When you look around Destin, it’s easy to see the growth, and Jeanne was instrumental in that.”

 

 

CAROLE SHAROFF, Atlantic Vacation Homes, Cape Ann, Massachusetts

After getting her master’s degree in anthropology and historical archaeology, Carole Sharoff took a job in Gloucester, Massachusetts, in the early 1970s working with at-risk teenagers who were restoring colonial burial grounds. Carole fell in love with the city and its history, and she developed a passion for collecting antiques by exploring local yard sales and consignment shops. A few years later, she bought an entire antique co-op building to sell her antique items.

Visitors would often come into Carole’s antique shop asking if she knew about any apartments or houses for rent or for sale. As a matter of fact—she often did, and Carole realized that real estate might be a more lucrative business than selling antiques. Seizing the opportunity in front of her, Carole obtained her real estate license and started renting out vacation homes that belonged to her friends before contracting with British company New England Country Homes which was expanding to the United States.

Today, over three decades later, Atlantic Vacation Homes is by far the oldest and largest vacation rental management company on the North Shore with 150 short- and long-term rental properties. Atlantic Vacation Homes has even been called the “rental agency to the stars” due to the many A-list actors, directors, producers, and film crews that stay in her homes. Carole Sharoff has been, and continues to be, a leader in both her community and in the industry serving in countless volunteer and nonprofit roles. Carole also cofounded the New England Vacation Rental Management Association and was elected to the Board of Directors for the International Vacation Rental Management Association where she served as secretary, membership chair, and a member of the credentialing committee. Through these roles, she worked to build industry standards, accreditation processes, and educational programs. Throughout her many leadership roles, Carole has spearheaded efforts and initiatives to bring diversity, equality, and inclusion awareness to the forefront.

“Carole embraces the next generation at every event, and every single time, it shocks me at how much she has spent of her career building up the industry while being completely successful in her own business. Whether it is promoting us, teaching us, or dancing with us, she’s just been the person that we all look up to in terms of the person in this industry who gives the most. Carole makes us all feel special and like we each belong. This entire industry owes her a debt of gratitude for everything she has done,” said Hinote.

 

Heather Bayer, Jeanne Dailey, and Carole Sharoff, were given the 2021 Vacation Rental Women’s Summit Pioneer Awards based on their ability to create the vacation rental industry we know today through hard work, perseverance, and dedication. We owe these women so much, and it was an honor to have the opportunity to celebrate them and their achievements at the 2021 Vacation Rental Women’s Summit. You will each continue to be an inspiration to us all. 

In honor of International Women’s Day and in celebration of these incredible women as pioneers of our industry, you can save 50% on the video package (5o sessions) from the Vacation Rental Women’s Summit with promo code IWD22.