How Jayne McCaw built an award-winning Muskoka luxury rental business

Starting with her own cottage in Muskoka, Jayne McCaw has spent six years growing her rental property portfolio to over 200 — taking on VRBO and Airbnb in the Muskoka luxury rental market. The 2019 RBC Canadian Women Entrepreneur Award Winner in the Start-Up category shares her journey.

By Karen van Kampen

Picture this. You pull into the driveway of a grand estate overlooking Lake Muskoka. A man in a white linen shirt is there to greet you. He helps you with your bags and invites you inside. There is a bouquet of fresh flowers in the entrance way. Sunlight filters into the great room that overlooks the lake. 

You peer down at the dock where you will have a private yoga session at sunrise. Your kids squeal and point at the massive water trampoline and kayaks they picked from a menu of concierge services. Your personal chef has champagne chilling. The fridge and wine bar are stocked.  All this is yours for the next two weeks, care of Jayne’s Cottages, a luxury rental and concierge company.  

“It’s like a mini version of the Four Seasons,” says Jayne McCaw, founder of Jayne’s Cottages. “Guests arrive, and it just happens.” 

Behind the scenes, there is a lot that goes into making a guest’s Muskoka dream a reality. With a staff of 75 cottage managers, cleaners, administrative and property personnel, Jayne’s Cottages works with every guest’s requests to create a personalized, five-star vacation in the woods. 

When Jayne’s Cottages launched in 2014, it was the first luxury rental company with concierge services in Muskoka. Now with more than 200 properties and a return rate of 50%, Jayne’s Cottages has become a trendsetter in the sharing economy, taking on VRBO and Airbnb in the Muskoka luxury rental market. 

The founder behind the eponymous brand is Jayne McCaw, whose success was recognized in 2019 with an RBC Canadian Women Entrepreneur Award in the Start-Up category, honouring a business that’s been showing profitable and sustainable growth during its three to five years in business.

Jayne built her award-winning business on her own Muskoka dream. When she bought her cottage on Lake Rosseau in 2010, Jayne’s realtor mentioned that the previous owners rented out the property for the month of July for $25,000. 

Jayne couldn’t believe her good fortune. “I’m so excited to have this cottage, and I can actually make money off it too?” she says. “It was a dream come true.” 

In 2011, Jayne began renting her cottage during the summer. The following year, Jayne rented out her property again and put the money toward a family trip to France. Finding a suitable place to stay in Provence was a challenge. Jayne was apprehensive about some of the properties listed on VRBO. 

Then she came across a woman named Beverly who managed a dozen properties in the Luberon Valley. Beverly’s company offered kayak tours and a personal chef while Beverly personally greeted her guests. Beverly gave Jayne “such a feeling of trust,” says Jayne. 

“That was the turning point,” says Jayne. “I returned home and I thought, there’s no Beverly in Muskoka.”  

 “Life’s too short not to realize your dreams, you’re losing years if you’re unhappy.”

In the summer of 2013 and 2014, Jayne rented out three cottages on Lake Rosseau, including her own. Then on Labour Day in 2014, Jayne quit her sales job at a technology company and launched her business. “I had turned 50 and I wanted to have more control over my life,” she says. 

Her goal was to rent out 15 cottages. “Then I could make it work financially,” says Jayne. “I just wanted to get out of the rate race in Toronto and spend more time at my cottage.”

She reached out to cottage owners, explaining how their properties would be safe in her hands. She would personally screen guests, take a deposit of 50% and have cottage managers and cleaners watch over properties by dropping in regularly. 

In 2015, Jayne had 25 properties for rent, 22 of which had never been rented out before. Today, she has more than 200 luxury properties that rent from $3,000 to $55,000 a week, which doesn’t include the menu of concierge services. Most owners continue to list their property with Jayne until they sell their cottage or decide to use their vacation property full-time.  

While she lists properties on VRBO as well as her website, Jayne says that 98% of bookings come from the Jayne’s Cottages site. Potential customers want to gather as much information as possible and talk to someone before making their purchase. 

Once guests have signed on with Jayne, their preferences and details are saved in the customer management system so that in the future, Jayne’s Cottages can review people’s requests, refer to their spouse by name or wish someone’s daughter a happy birthday. “Business today is about being more personal and providing the best customer experience,” says Jayne. 

Jayne has a full-time photographer and posts new content on her website several times a week. This engages potential customers while maintaining the company’s strong organic search results. When Googling luxury Muskoka rentals, Jayne’s Cottages is listed before VRBO and Airbnb.

With 22% of her visitors from the U.S., Jayne ensures her digital marketing efforts target non-Canadian as well as local clientele. This includes some conquest marketing in which she is targeting people looking at luxury properties in the Hamptons, Martha’s Vineyard and Nantucket by promoting the safety and natural beauty of the Canadian wilderness, all paid in Canadian dollars. 

Several government and technology grants have also helped Jayne grow her business. Last year, she was awarded a $75,000 grant from the Ontario Centre of Excellence. With the help of Georgian College’s Big Data Technology program and graduate IT students, Jayne built an integrated technology platform to better serve her customers. 

Jayne’s goal is to continue drawing more people to Muskoka, the inspiration behind her business. “Life’s too short not to realize your dreams,” says Jayne. “You’re losing years if you’re unhappy.”