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Siesta Key vacation rental business launches national company

Heather Plampin founded a vacation rental management business out of near-broke desperation. Now, with attention to detail — and marketing — she’s targeting clients outside the region.

  • By Mark Gordon
  • | 5:00 a.m. July 28, 2023
  • | 2 Free Articles Remaining!
Heather Plampin founded The Cottages on the Key in 2008.
Heather Plampin founded The Cottages on the Key in 2008.
Photo by Mark Wemple
  • Manatee-Sarasota
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Some 20 years ago Heather Plampin had a booming home renovation business, especially doing work after Hurricane Charley ripped through Charlotte County. 

But that business nearly evaporated when the housing market tanked and work dried up. Plampin and her father Roger Van Wie, also in real estate, “both just got wiped out,” she says.  

“We had no income, we had nothing,” she says. “We were in a really bad way. We decided to see if we could salvage our very last asset — our homes.”

That was in 2008. Airbnb had just launched. VRBO was around, but more a niche business than a global vacation rental brand. Yet Plampin dove right in, renting out her home in Sarasota. Her dad rented out his home on Siesta Key. Then Plampin, her husband and her father — and their pets — moved into an annual rental place together.  

Not only did Plampin generate some life-saving income, she also found a new business opportunity. “It was great,” she says. “It was exactly what we needed.” 

Plampin, 45, has since turned that desperation into a thriving business, The Cottages on the Key, and more recently what she believes can be an even bigger business, in taking her model nationwide. After a decade-plus of growing the business organically, her growth mindset for both The Cottages and the new entity, The Compass Collection, she says, comes not necessarily from revenue goals, but a calling. “There’s been a real shift in housing, she says, “and we can really help homeowners.” 

The Cottages is a full-service concierge vacation rental market company, focusing on Siesta Key, that provides a variety of services for a vacation homeowner who in many cases lives far from Florida. The Cottages is on track to handle some $14 million in revenue for property owners this year spread through a portfolio of 65 owners and 80 properties. 

While the revenue figure is nearly double 2020, it’s come at cost. “Since the pandemic business has been explosive,” she says, “but also very volatile.”

The volatility stems mostly from the housing market. Prior to the pandemic, most of The Cottages’ homeowner clients, Plampin says, were buying properties and holding them for five years — at least. Now in some cases clients own a home for a year or two, then flip the property. That makes building and maintaining long-term relationships tougher. “It’s much more fluid than it’s ever been,” she says. 

Plampin, meanwhile, more recently launched The Compass Collection to handle luxury vacation rental management from afar. That company, she says, uses The Cottages’ process and systems, honed over 15 years, to do everything for the homeowner but be on site to fix the leaky faucet or busted garage door. The Compass’ model is to work with vacation homeowners across the country, from Park City, Utah to Nashville to the Hamptons in New York. 

The idea for The Compass Collections comes partially from Matt Farhat, who joined The Cottages in business development in 2021. After working with clients for a bit, Farhat went to Plampin with a proposal: why not take the firm’s collective expertise in vacation rental SEO, dynamic pricing and algorithms into a national enterprise? She embraced the idea. “We do everything that gets the guests to the door,” says Farhat, a former social studies and physical education teacher in both Sarasota and Manatee counties before he joined the company. 

Compass Collection officially launched in April. 

Steady and ready

In a sense, Plampin and her team at The Cottages have two separate but highly-connected clients. There’s the homeowners who pay a fee to the company for the services. And then there’s the guests. The rental rates the guests pay — as high as $10,000 per week during high-season for some properties — goes to the homeowners. 

That model is standard for the industry but what sets the firm apart, according to Plampin and some of the company’s clients and employees, is its devotion to details and customer service. "I want every guest to be full of happiness in every way possible,” says Plampin. 

The company’s way there is through its eight-part credo, which includes ideals such as finding a way to get to yes; being proactive not reactive; and eliminating silos. Overall, Plampin says the credo is The Cottages’ way of bringing back “the lost art of hospitality.”  

The company has 10 employees, in addition to a group of freelancers and on-demand employees. Her past few hires, including Farhat, have been A-players, Plampin says, but recruiting and retaining staff remains a top priority. She says finding, and even keeping, people hasn’t been as big a challenge as making sure the people the company does hire are in the right seats, doing the right things for the company. Citing a common second-stage entrepreneur challenge, Plampin says “I have to figure out how to scale and how to grow” without losing the high-touch personal service connections that makes The Cottages successful. 

One way Plampin handles hiring and building a successful team is by using an Orlando company, Better Talent, that exclusively finds employees in the vacation-rental industry. The company’s process includes personality tests Plampin heavily relies on. 

Asked who she emulates in hospitality or a company she’d like The Cottages and The Compass to be like, Plampin cites neither the Ritz-Carlton or the Four Seasons. Instead, it’s more of a mass consumer brand: Publix. “I’ve always admired the way George Jenkins created a culture base there,” she says. 

Plampin’s leadership style, of empowering employees and creating a positive team-driven environment, has paid off, says Farhat. From staying calm before hurricanes to handling a slew of mini and random crises that can envelop a day, Farhat says Plampin remains steady. “She can handle adversity like no one else I’ve ever seen,” she says. “We’re all out there chopping wood every day, grinding. She is somebody who we are very happy to follow.”

Stay current 

An underlying business reason for the company’s success, outside its credo and culture, goes back to a realization Plampin had a few years ago about its place in the market. “We call ourselves a vacation rental company that’s hidden as a marketing company,” she says. 

That mindset has guided the company’s decision-making process on where and how it spends its marketing dollars — some $300,000 a year, Plampin says. That includes the standards, like Airbnb and VRBO ads, to digital billboards in unexpected places. The company focuses mostly on a higher-end clientele, and because of that, Plampin says the changes in vacation rental regulations in municipalities has had little impact on the business. 

“We market to multigenerational families,” she says. “We are not here to bring the party to Siesta Key.”

A second reason for the company’s success, says Farhat, is that it takes the time to build relationships with current clients, looking within for more opportunities as opposed to always chasing the next big deal. Not that Farhat and the company turn away new homeowners, but, he says, “our current client is our best client.”

That approach resonated with Chris Nantista, a multifamily investor from the Midwest who recently bought his first building in Florida. Nantista, through CFC Investment Group, paid $2.3 million in January 2022 for a six-unit building on Avenida Veneccia on Siesta Key, near Siesta Key Village. He spent another $500,000 on renovation, he says, and hired The Cottages to oversee the upgrades and handle the property management of the complex, now called CJ’s on Siesta. And while Nantista took a chance he says, on not using a bigger corporate entity with deeper pockets for property management, he’s been impressed with Plampin and her team.

“Most management companies just want to send you the check and have you out of the way,” Nantista says, “But (The Cottages on the Key) is very owner-centric. They really want the owner to do well, which isn’t something you see every day in this field.”

Correction: This article has been updated to correct the spelling of Roger Van Wie’s name.



Mark Gordon

Mark Gordon is the managing editor of the Business Observer. He has worked for the Business Observer since 2005. He previously worked for newspapers and magazines in upstate New York, suburban Philadelphia and Jacksonville.

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