Seasonal Employee Retention: 5 Tips for Rental Businesses

One of the biggest challenges rental business owners face each year is seasonal employee retention. It’s an issue that simply comes with the territory: How do you cultivate a loyal team when you aren’t in a position to offer year-round employment?

Here are a few tried-and-true tips on how to incentivize part-time employees to stick with you:

1. Give Them a Sense of Pride in Their Role

“It’s the little things—especially for recent college graduates. Spend $25 on business cards and give them to your employees so they can show them to their parents, pass them out to family and friends, and give them to prospective customers. Little stuff like that is really nice.”— Jon Wilson, Co-owner, Action Watersports of Incline Village

It doesn’t matter if you run a bank, manage a small boat rental business, or own a chain of coffee shops: Being a great place to work is linked to outstanding business results, according to the Workforce Institute.

Taking steps (even small ones) to show workers they’re valued members of the team can instill pride, boost morale and a encourage a sense of ownership in the company—all contributing factors that might entice them to keep coming back, season after season. Jon points out that even simple gestures, such as ordering business cards for your top workers, sends a message that they’re valued.

Quick tips:

  • Give your best workers some extra authority and responsibility
  • Hand out business cards
  • Give everyone a title, e.g. “dock manager,” “beach manager,” “rentals specialist,” etc.
  • Recognize and reward an employee of the week or month
  • Look for opportunities where employees can develop additional skills while working for you, and encourage team members who might by shy or hesitant to take on new challenges or responsibilities outside their wheelhouse.

2. Better Business Tools = Better Workday = Better Seasonal Employee Retention

“I can’t believe this company survived without an online booking system before.”— Jon Wilson, Co-owner, Action Watersports of Incline Village

Having the right operational resources in place can spell the difference between a chaotic workday, vs. a workday that runs like a well-oiled machine. If you’re trying to run a growing business—but still using outdated methods for managing reservations, payments, scheduling and customer communication—your team might not be jumping up and down to return next season.

Adopting smart and easy-to-use technology such as online booking software can drastically streamline the day-to-day minutiae for your employees, and enable them to be more efficient (and happy) at their jobs.

Adopting online booking software can drastically streamline the day-to-day minutiae for your employees

Prior to implementing an online booking software, Action Water Sports “would hand-write a sheet of what boats were going out at what time and bring that down to the dock every single morning,” Jon recalls. “We had five people in our gazebo, and we had a clipboard for each product (catamaran, jet-ski, kayak, etc.) So whoever had the one clipboard, they were the only person who could take a reservation.”

Nowadays, thanks to their robust online booking software, Jon’s employees can…

  • Easily track inventory from one place with a check-in, check-out feature
  • Receive daily manifest reports automatically via email
  • Accept walk-ups and manage reservations from anywhere using a mobile app
  • Stay up to date on things like weather warnings and reservation cancellations via a real-time dashboard
  • And a whole lot more

For rental businesses that also offer guided tours, an online booking software like Peek Pro lets managers set up “Guides” in the backend and assign them to lead specific tours or trips. The Guides can then receive automated text and email notifications updating them on key details, such whether they’ve been assigned/unassigned to an experience, reservation cancellations or changes, etc.


  1. It Pays to Pay More

When we spoke with Jon, he was quick to address the core issue most summer or winter-oriented businesses face.

“One of the hardest things we have to deal with is our staffing. We’re a seasonal business and we’re a transient community where it’s hard to get people year after year,” he explained. “We’ll be lucky to get people to work with us for three seasons. We’re constantly re-hiring and re-training, and it’s tough to staff.”


Photo courtesy Kayak Annapolis


Eventually, Action Water Sports made a game-changing decision to start paying some of its top team members year-round on salary, and it’s made a big difference with seasonal employee retention, Jon said.

While this strategy isn’t practical for small seasonal businesses just getting into the game, it’s worth considering down the road as operations grow, especially from a financial perspective: The typical cost of turnover for positions earning less than $30,000 annually is 16 percent of an employee’s annual salary, according to the Center for American Progress.

4. If You’re a Summer Business, Team Up with a Winter Business (and Vice Versa)


“If you basically work it out to where the employees have guaranteed work between your company and another company year-round, it’s a win-win for everyone involved.”— Jon Wilson, Co-owner, Action Watersports of Incline Village


We especially love this out-of-the-box suggestion from Jon: Explore the possibility of setting up a partnership with a business that operates during your off-season. For example, if you’re a kayak/SUP outfitter in an alpine lake area, do some networking and establish a relationship with someone who specializes in wintertime experiences, such as snowmobile rentals. If you “basically work it out to where the employees have guaranteed work between your company and another company year-round, it’s a win-win for everyone involved,” Jon suggests.

5. Perks Work, Too—Even Little Ones


“We do a lot of donations to our community, so we get invited to things like golf tournaments and crab feeds, and we tend to pass that stuff on to our staff.”— Jon Wilson, Co-owner, Action Watersports of Incline Village


Photo courtesy of Kayak Annapolis


Understandably, many small and mid-size companies aren’t in a position to offer more pay. But there’s other ways to get creative: Even in low-stakes, seasonal jobs, doling out perks can also encourage seasonal employee retention. According to Jon, this can be as simple as re-gifting freebies or giving employees a paid day off to go do something fun in the area.

If you’re running a rentals business, consider giving out a “friends and family” pass to each employee so they can bring a few pals on one of their off days. Or perhaps designate one day of the week “team breakfast” day, and bring in bagels, fruit and coffee for everyone to enjoy before their shift.


Your seasonal business doesn’t have to be a summer job slacker destination just because it’s only in full swing for half the year. Using these creative work-arounds can help foster better seasonal employee retention and a direct line to business growth.