Vacation Rental Women’s Summit Honors Heather Bayer, Jeanne Dailey, and Carole Sharoff with Pioneer Awards

Vacation Rental Women’s Summit Honors Heather Bayer, Jeanne Dailey, and Carole Sharoff with Pioneer Awards


The 2nd Biannual Vacation Rental Women’s Summit was held at The Ritz-Carlton hotel in New Orleans in December, and as the vacation rental industry’s first-ever women-focused event, we had the honor of presenting Pioneer Awards to three outstanding women.

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, each played essential roles in building the vacation rental industry into what it is today.


Today, condos and vacation homes take up as much, if not more, vacation real estate as hotels and resorts, but that wasn’t always the case. When each of these women founded and started their businesses, more families were opting for places to stay aside from these vacation rentals. As the vacation rental industry grew, each of these businesswomen excelled in managing change, building successful businesses, and working with their destinations and the industry as a whole to provide vacation rental accommodations that will exist for generations to come.

“There are just some women in our industry who have led the way, and we have all benefitted from it. It wasn’t hard to come up with the women we wanted to honor this year,” said VRM Intel Founder Amy Hinote.

HEATHER BAYER, CottageLINK Rental Management, 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 to a Canadian father and British mother who 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 that we know today as a pioneer in the vacation rental industry was ignited in August 1997 when her family traveled to Canada for family weddings 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. Within six months, she had formed her first rental company Clearwater Holidays, and inventory rapidly grew to 30 to 40 properties as word got out. The biggest challenge of this model was to raise property standards and improve education. With her husband’s impending retirement from the Air Force 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 college catalog. With a continued focus on new own acquisition and education, inventory grew to over 100 properties, and the need for an educational resource was born. Heather’s website was launched in 2006 as the blog to help the company’s owners improve the quality of their rentals, and in 2014, Heather created a podcast to help rental business owners while in the car on the move, becoming a good addition to the resources available.

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 Amy 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 female 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 Amy Hinote. “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 so 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 co-founded the New England Vacation Rental Management Association and was elected to the Board of Directors for the International VRMA 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 Amy 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 from the 2nd Biannual Vacation Rental Women’s Summit with promo code IWD22

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