Navigating Difficult Owner Conversations During a Booking Slowdown
(With Honesty, Data & Strategy)
If you manage short-term rentals, you’ve likely had some tough conversations lately. Owners are asking the hard questions:
“Why aren’t we fully booked?”
“What’s going on with the market?”
“Are we doing enough?”
Owners deserve clear, honest answers. The key to these conversations isn’t just being optimistic. It’s about being real, bringing the data, and showing up with a strategic plan.
Start With Empathy and Facts
These are people who’ve invested in their homes and in you. When bookings slow down, it’s personal for them. The best way to start the conversation? Be transparent and data driven.
Let them know the truth about the current market temperature:
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Shorter stays are the new trend.
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People are traveling closer to home.
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Midweek bookings are slower across the board.
For example, in my specific market, the Texas Hill Country, we're seeing an increase in 2- to 3-night stays and a drop in overall stay length. This aligns with national data showing travelers are prioritizing affordability and flexibility, and they want value more than ever.
Use the data to take the emotion out of the conversation and give owners a bigger-picture perspective. They’re not alone; it’s not their property that’s underperforming; it’s a shift in guest behavior.
Reframe the Narrative
It’s natural for an owner to hear “shorter stays” and think “less revenue.” But here’s where we reframe the conversation.
Say something like:
“We can take advantage of this shift. Two 3-night stays with just one night in between could bring in the same or more revenue than a weeklong stay and it gives us flexibility to fill gaps.”
Then show how you’re pivoting:
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Marketing to nearby cities -where people are still booking, just on shorter timelines.
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Promoting 3-night getaways - perfect for long weekends or spontaneous trips.
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Optimizing pricing to be competitive while preserving value.
When you position the challenge as a new opportunity, it helps owners shift from worry to strategy.
Present a Clear Plan
The most reassuring thing you can give an owner in a tough conversation is a plan of action. Here’s what that might include:
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Running a limited-time promotion (with a discount code or bundled perk).
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Offering early check-in or late checkout to boost perceived value.
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Adding bonus amenities, like a free golf cart rental, beach gear, or bikes.
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Adjusting the calendar to allow shorter minimum stays, while closing high-gap nights.
You can also show how you're working to minimize unoccupied nights.
For example: “If we have two 3-night stays and only leave one night empty, that’s a 6-night booking week, it's not a bad outcome at all.”
This shows you’re being proactive, not passive, and that’s the confidence owners need to hear.
Focus on Long-Term Value
Remind owners that these small changes aren’t just about riding out the current dip, but it is about positioning their property to perform well in any market.
With the right strategy, short-term fluctuations can actually increase visibility, attract new guest types, and earn better reviews through thoughtful experiences. You are not just here to fill nights; you are here to build up their investment.
Final Thoughts: It’s Not Just a Conversation — It’s a Partnership
At the end of the day, difficult conversations are part of managing owner relationships. But with the right approach, rooted in data, empathy, and action, these moments can strengthen trust.
When owners see that you’re not just reacting, but strategizing, they’ll remember why they chose you in the first place.
Cheers to a long relationship!!
About Denise Morris
A Fredericksburg, Texas native, Denise Morris brings over 35 years of experience in the vacation rental industry. Formerly Director of Operations and Director of Owner Relations, she built trusted relationships with property owners while expertly balancing operational demands. Denise is known for her deep knowledge of property management software and her ability to enhance communication and transparency.
Affectionately called “The Queen of Culture,” Denise is recognized for creating genuine connections and fostering positive team environments. Her blend of operational expertise, tech fluency, and heartfelt leadership makes her a respected and authentic voice in the industry.
