Posted 3 months ago

What I Learned Managing 25+ Short-Term Rentals

When I started managing a cute little vacation cottage for a friend five and a half years ago, I really didn't know what I was getting into. I thought success would come down to the right furniture, good photos, and taking excellent care of our guests.

Those things matter — they are the foundation, but they’re not what actually moves the needle on profit.

I eventually built and ran a boutique short-term rental management company with 25+ properties. Looking back, there are a few lessons I wish I had understood much earlier — especially when I was still in the “I can handle this myself” phase.

Here are the biggest ones.

1. Pricing isn’t a set-it-and-forget-it decision

Early on, I treated pricing like a task:

Pick a tool
Set a base price
Trust the algorithm

What I came to understand was that pricing is a strategy, not a setting.

Once you get the hang of the basics of hosting guests, you start to find yourself focusing on revenue, and the questions change:

How far out are bookings pacing?
What exactly is RevPar, and how do I use that info?
Where are gaps forming?
Are weekends carrying weekdays, or vice versa?
Am I optimising for occupancy or margin — and why?

Dynamic pricing tools are vital tools, but they don’t replace insightful decision-making. They amplify whatever strategy you give them — including bad or outdated ones — those based on panic or what your gut tells you.

2. Revenue problems often show up as “operational stress” first

A lot of times, if we are looking for clues, we can see our problems early on by pausing to dig down, notice, and name the challenges. Before we verbalise, “Revenue is down,” we often say things like:

“I feel like I’m working harder for the same results”
“Bookings feel unpredictable”
“I don’t trust what’s coming in anymore”

When I was managing just a few properties, I thought this was just part of hosting.

Over time, I learned that these feelings were an early sign that:

Booking windows are shifting
Rates aren’t aligned with demand
Or the market has changed, and the strategy hasn’t

Catching this early is critical. You can head off issues before they snowball.

3. More properties don’t automatically mean more clarity

This one surprised me.

Adding properties didn’t make things simpler — it made patterns harder to see. Every property has its own nuances.

Without intentionally stepping back to review performance:

One strong month can hide a weak strategy
One great property can mask underperformers
Gut feelings start to replace data

I keyed in on conducting consistent and honest reviews of each of my properties' performance using data tools.

4. The biggest revenue gains come from small, boring adjustments

Most meaningful revenue improvements didn’t come from:

New furniture
New amenities
New platforms
(although these can all have a positive impact)

Instead, I saw consistent improvement in revenue/profit by pulling different levers:

Slight changes to minimum stays
Adjusting lead-time pricing
Rethinking shoulder-season strategy
Being honest about what a property is (and isn’t) good at
Reviewing and adjusting fees
Considering more flexible cancellation policies

None of this is flashy — but it’s effective.

5. Getting a second opinion is a strength, not a failure

This is the one I wish I’d learned first.

For a long time, in the back of my mind, I thought needing help meant I wasn’t good at this. Since I came to short-term rentals with no experience in that specific industry, I had a bit of impostor syndrome. I was becoming burned out, unable to keep up with all the details, growing my portfolio; I thought I should be able to handle it all.

Now I see it differently:
Running short-term rentals is complex. Markets shift. Guest behavior changes. Platforms evolve. Competition changes.

Having someone look at your numbers without emotional attachment can save months (or years) of trial and error. I finally hired a revenue manager to provide perspective and help me apply the data effectively to my pricing decisions.

This was so impactful on the success of my business that, after I sold my boutique management company, I decided to help others in the same way my revenue manager helped me.

If you’re a STR owner, investor, or boutique manager and ever want a second set of eyes on pricing or performance, I'm always game to chat. I really enjoy sharing what I learned.

Wishing you happy and profitable hosting!