The Women Who Shaped Short-Term Rental History

The dudes got all the headlines and — let’s face it — because of ingrained sexism and the traditional old boys’ networks, they took an inordinate share of the top jobs, but there were many talented women leaders and entrepreneurs who likewise shaped the history and trajectory of the global short-term rental industry.

These women included Aurelie Lepercq, who ran HomeAway’s Europe business for a half-dozen years; Jennifer Hsieh, who incubated and launched Marriott’s Homes & Villas; Jeanne Dailey, a property manager who created DestinVacation.com, and the relatively anonymous women who scanned photos to build listings in VRBO founder David Clouse’s basement. There are many more.

Many of these women entrepreneurs went on to lead their own short-term rental companies: Lepercq is CEO of Edge Retreats in London, Rhonda Sideris is the founder and President of Park City Lodging in Park City, Utah, and Merilee Karr is the founder and CEO of UnderTheDoormat Group in London and is the chairperson of the UK Short Term Accommodation Association.

Skift documented many of their personal and business stories in the Skift Definitive Oral History of Short-Term Rentals Part 1, Part 2 and Part 3.

Aurelie Lepercq, Former HomeAway Europe General Manager and CEO of Edge Retreats

Lepercq isn’t buying the notion that patriarchy stood in her way.

“In my 16 years in the vacation rentals industry, I have not personally experienced an old boys’ network or sexism,” Lepercq said in an email over the weekend. “Quite the contrary: The two founders of the leading vacation rentals business I worked with in particular are not only exceptional professionals but also supportive human beings. The Board also had women representation very early on in the journey of the business.”

The Edge Retreats CEO, however, acknowledged that the venture capital arena is stacked against women and minorities.

“It is true that there are more men than women in senior and founding roles in the industry, as is the case in other sectors,” Lepercq said. “Where we need to look is how currently-minitory-led businesses are supported through financing. The stats are not legend: Only 2 percent of VC funding goes to women-led businesses and even less goes towards black and latino founders despite everyone’s efforts to change the game. So something is still amiss.”

In London, Lepercq joined Holiday Rentals, which HomeAway acquired in 2004, and then ran various parts of HomeAway’s European business. On entering the industry, she said, “there was just something there that just needed to be done and could change a sector.”

Ever wonder how HomeAway managed to make dozens of acquisitions of vacation rental businesses with such divergent technologies and blend them all, more or less?

HomeAway made 19 acquisitions when Lepercq worked there, and said the company used Holiday Rentals as the tech foundation to stitch them together.

You can read Lepercq’s story in the oral history Part 1 and Part 3.

Jennifer Hsieh, President of Homes & Villas by Marriott International

Jennifer Hsieh, president of Marriott’s luxury vacation rental business, Homes & Villas, was instrumental in proving the benefits of the concept to Marriott International leadership, and then launching the brand with a very small team.

“Another data point that was brought to us, was 27 percent of our guests in 2017 had stayed in a home, and that meant they were leaving our portfolio. And that data point for Arne (then-CEO Arne Sorenson) and for Stephanie (current Marriott President Stephanie Linnartz) was an aha moment,” Hsieh said in Part 3 of the oral history. “Why would we want 27 percent of our guests to leave our portfolio versus staying within Marriott, Bonvoy?”

Merilee Karr, Founder and CEO of UnderTheDoormat Group

Like Lepercq of Edge Retreats, Merillee Karr thinks male investors tend to skew their funding toward people with similar profiles.

“I would always believe that it’s about finding the right people, and I’ve got incredible investors who are men,” Karr said. “I do think that in the entrepreneurial world, people like to invest in people like them, and there are simply more investors who are male out there, and they’re more in the property world. There are more people who see themselves in male entrepreneurs than females. So I think that is just the reality. I mean, have I ever really felt there was a specific thing where I was like, “Well, I didn’t win that because I was a woman.”? No. But do I feel like you almost have to prove yourself twice as much? I think sometimes the answer to that has to be yes.”

Karr had been a triathlete and a procurement manager for Shell Retail in Europe, and found herself planning group trips with friends to holiday rentals, where she could squeeze in her bike with less hassle than in hotels.

UnderTheDoorMat was an early partner with Marriott’s Homes & Villas, which Karr saw as an endorsement for her business because of what she described as Homes & Villas’ high standards. You can read her story in oral history Part 1 and Part 3.

Jeanne Dailey, Founder and CEO, Newman-Dailey Resort Properties

Jeanne Dailey recalls everything changing in the late-1990s when Florida loosened regulations of vacation rentals, and the Internet changed how people found and booked vacation homes.

“So I had a really good web developer who I utilize now, and his previous boss helped us get a good URL, which was destinvacation.com,” Dailey said. “We started to just build that. Instead of one photo in a brochure, it might allow for 10 photos then, but 10 was way better than the one. And at this point you didn’t even have online booking. You were just barely starting to take credit cards instead of waiting for checks to come in and clear. You can read Dailey’s story in oral history Part 1.

Kim Rubey, Former Head of Airbnb Communications

Kim Rubey joined Airbnb in 2011 when it was approaching unicorn status, but wasn’t necessarily a mainstream brand. Naysayers in the press dismissed Airbnb’s potential, Rubey said.

 Airbnb’s founders “were big believers in the power of public relations from the very beginning,” Rubey said. “The mandate was build out a world class team, find us ways to get as much exposure as possible, and really use PR to help shape the brand.”

Airbnb’s launch in Cuba was an all-time career highlight for Rubey. “A few of us went at various times in the first couple of months of 2015, and we came back and made the case to the founders of how we should work really quickly and try to establish a presence there. Brian (Chesky) challenged us to be able to have 1,000 listings online by April. The casas particulares hosts don’t have internet. It was a gargantuan effort, but similar. A lot of people throughout the company came together and were super motivated by having this audacious goal. It was just phenomenal to go back there in the following years and to hear from the hosts. They loved hosting to begin with, but then, to have so much more demand and volume and meet more people, it really just then personally game-changing in a financial way for them.”

You can read Rubey’s story in oral history Part 1 and Part 2.

Rhonda Sideris, Founder of Park City Lodging

Rhonda Sideris founded Park City Lodging in 1984, first handling the property management for owners with a property or two looking to host ski vacations, and graduating to managing homeowners associations by the 1990s.

The pandemic was a time of robust expansion for her company as Sideris saw her portfolio grow from “120 properties in March 2020 to probably 286 in December or January of 2021,” Sideris said. You can read Sideris’ story in her own words in oral history Part 1, Part 2, and Part 3.

Sandra Brown, Vacation Rental Owner in Muskoka, Canada

Sandra Brown and her husband own and host a couple of holiday cottages, including one that accommodates 20 people, a popular vacation region, Muskoka, Canada.

Brown previously managed recruitment for a major bank in Canada and had project management experience, which comes in handy in dealing with the twists and turns of the vacation rental business. And, for Brown, it’s definitely a business, not a hobby or passion project.

“But at the end of the day, this is a hospitality business,” Brown said. “A lot of people don’t really understand how to do this right. They think they can just throw their property on the platform and off they go, and they don’t really have to think about it, and that’s bullshit. And I have to say, we seem to know what we’re doing. We’re very successful.” You can read Brown’s story in oral history Part 2.

Pamala Parris Wideen, Host, Tavares, Florida

Pamala Parris Wideen hosts a couple of properties in Tavares, Florida, mostly for families visiting for fishing tournaments, weddings, and funerals.

Parris Wideen finds a lot of her guests through Vrbo and Airbnb, but likes to solve any customer service issues in-house if she can.

“We put it on Airbnb and Vrbo,” Parris Wideen said. “I prefer Airbnb, and most of our business goes through Airbnb. Vrbo, their app is clunky, the calendar doesn’t always sync right. With the Airbnb one, I mark off a day before and a day after. I’ve got this paranoid thing that it won’t get cleaned in time or whatever. And Vrbo, you don’t have that option to mark off a day before, or a day after. And then, when you go into the app, there’s just so many more steps you have to do to access everything.”