Ep679 – 2026 Pricing Strategies Every Short-Term Rental Operator Must Use

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In this episode of Get Paid For Your Pad, Kaye Putnam (Head of Marketing at Freewyld and Freewyld Foundry) sits down with Jasper Ribbers to unpack the newest KeyData trends report and the surprising disconnect between what operators say they prioritize and what actually moves revenue. Pricing was ranked the number two priority for 2026, yet ADR is flat, competition is rising, and most operators still lack a real pricing routine.

If you are an STR operator who wants to improve pricing strategy, reduce dependency on OTAs, and understand why mid sized companies are positioned for the most growth, this episode is a must listen. Jasper and Kaye break down why operators leave 20 to 30 percent of revenue on the table, what expert revenue managers do differently, and how pacing and process create meaningful gains even in weak markets.

You will hear:
Why ADR is flat nationally and why real ADR is falling once inflation is considered
What causes operators to think they are performing well while still missing major revenue
Why most pricing tool usage is reactive instead of strategic
How daily, weekly, and monthly pricing routines drive better decisions
Why only a small percentage of operators understand pacing and how it impacts performance

We also talk about:
Why so many STR teams stay stuck solving urgent tasks and never get to pricing
How rising Airbnb suspensions are pushing operators toward OTA diversification
Why mid sized operators are the most optimistic for 2026 growth
How the 2026 World Cup could create demand spikes across the United States
What operators should expect once the December 5 team draw is announced

🎯 Mentioned in the Episode:
Freewyld Foundry Revenue and Pricing Management
KeyData 2026 Trends Report
Topkey pacing webinar
Pricelabs industry insights

🔥 Favorite Takeaway:
“You do not know what you do not know. Many operators believe they are already optimized until real revenue management reveals how much they were missing.”

📍 Want us to audit your pricing strategy
Get your free, personalized revenue report at FreewyldFoundry.com/report.

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Jasper Ribbers
If you have a revenue manager overseeing your portfolio and that person does not know how to maximize revenue, you might be leaving 20 to 30 percent on the table. Many operators believe they are doing well because they have high occupancy or perform better than the market, so they assume there is not much upside. The reality is that you do not know how much revenue you are missing. We can estimate potential gains with more accuracy now, but the only way to know is to implement the right strategy and see the results. The difference can be significant.

Kaye Putnam
KeyData’s newest trends report shows that most operators say pricing is a top priority, yet ADR is flat and competition is rising. If everyone says pricing matters, why is revenue not improving? Today we will unpack what the best operators are doing differently with pricing, tech, and OTAs, especially mid sized companies that KeyData calls the growth engine of the industry.

Jasper
Thank you for the invite. I am excited to dive in.

Kaye
Welcome back to Get Paid For Your Pad. I sent you the report, and here is what stood out to me. They interviewed around 240 operators across different sizes and markets and asked what they were most focused on for 2026. Number one was marketing and distribution and number two was pricing. As a marketer, that felt like strong confirmation that we are in the right place at the right time. What stood out to you?

Jasper
These reports come out year after year. Pricing has been the number one or number two focus for at least five years, but operators rarely act on it. I hope 2026 will be the year when revenue management finally gets the attention it deserves.

Kaye
Why do operators say pricing is important but never take action? What stops them?

Jasper
Short term rentals have many urgent, reactive tasks. If a cleaner cancels and guests are arriving soon, operators will always prioritize that over pricing. They tell themselves they will work on pricing tomorrow, but something else always comes up. Pricing never feels urgent, so it gets pushed back.

Most operators also do not know what they should be doing in their pricing tools. They log in, look at numbers, make a few random adjustments, and hope it works. They lack a real strategy, a daily plan, and clarity about which data points matter. We follow a daily, weekly, and monthly process. When I start my day, I know exactly what to review and how to make decisions. Many operators do not have that.

When we ask operators applying for a revenue report about their process, we get completely different answers from everyone, and most admit they are making random adjustments. There is also very little education in STR revenue management. In hotels, you can study revenue management at Cornell. We do not have that equivalent in this industry.

Kaye
The report mentioned that national ADR is flat. What are you seeing in market and demand trends?

Jasper
Many markets are weaker than last year. Texas is a good example, especially San Antonio, which is down around 20 to 30 percent. If ADR is flat nationally, many markets might actually be slightly down. And with inflation, real ADR is declining because one hundred dollars today is worth less than one hundred dollars last year. ADR would need to increase four or five percent just to break even. It is a challenging market.

Kaye
This explains why operators feel pressure. Even if ADR is flat, purchasing power is dropping. Given that environment, what can an expert revenue manager actually do?

Jasper
A lot. It depends on how strong your current strategy is. I recently did a pacing webinar with Topkey. Only around one in twenty companies that apply for a revenue report are already doing an excellent job. The challenge is that operators do not know what they do not know. Many believe they are performing at the top of the market until their revenue increases 15 to 25 percent after we apply a real strategy. They are surprised because they thought they were already optimized.

Revenue management is powerful because revenue increases go directly to the bottom line. Most ways to grow revenue require investment, like new photos or amenities. Improving revenue management has no extra cost. Many operators use low cost revenue managers who are not actually maximizing revenue. One client used a very affordable manager overseas and thought it was a great deal. After switching to us, their revenue increased so much that our service effectively costs them nothing because the additional revenue is greater than our fee. The cost of a revenue manager is not what you pay them. It is the revenue you lose if they are not skilled.

Kaye
Missed revenue feels invisible, but the opportunity cost is very real. The report also showed that mid sized operators are the most optimistic about 2026. They are more tech forward, use pricing tools more often, and are more data engaged. Does that match what you see?

Jasper
There are three groups. Very small operators may not focus much on data. Large operators have more structure but may struggle to make big strategic shifts. Mid sized operators, with 25 to a few hundred listings, usually have the most opportunity. They have enough scale to benefit from strategy but are still small enough to move quickly.

Kaye
They have resources but can still adapt fast. Another interesting section of the report focused on OTA dependence. Direct bookings make up 26 percent of reservations but 38 percent of revenue because of longer stays and higher average rates. Airbnb accounts for 45 percent of bookings but only 34 percent of revenue. What are you seeing with OTA mix?

Jasper
Airbnb’s recent changes have pushed operators toward more OTAs and less dependency on Airbnb. If your rating drops slightly, your visibility can fall dramatically. Suspensions happen more frequently now. Because we manage many listings, we see suspensions almost daily.

Direct bookings usually involve longer stays. I am currently looking for a two month stay in the Netherlands. I will not book that directly on Airbnb. I will contact the host and negotiate. That is common behavior. Direct bookings have been a focus for years, and current Airbnb challenges are accelerating that trend.

Kaye
We recently interviewed Beth, one of our clients, who reached one thousand five star reviews. It is possible, but it takes a lot of work. When you manage revenue across different channels, do you aim for price parity?

Jasper
Clients usually prefer the direct channel to be the cheapest. Full parity across OTAs is almost impossible because each platform has different discounts. On Booking.com you must use Genius and mobile discounts or you lose visibility. If your base rate is one hundred dollars and you add a markup plus multiple discounts, the final price paid can vary widely. Perfect consistency is unrealistic unless you avoid discounts, but avoiding discounts costs more than price differences.

New listings sometimes require pushing a specific platform to gain reviews or visibility. In those cases direct might not be the cheapest option temporarily.

Kaye
There is always nuance in revenue management. What are you excited about for 2026?

Jasper
The FIFA World Cup. I am excited as a fan, but it is also a major opportunity for operators. Games will drive demand, especially in host cities, but also across the country. Travelers will visit other destinations while they are here. We do not know the exact impact yet, but it will be significant. On December 5 the draw will reveal which teams play in which cities. The fan bases matter because some countries will send many visitors.

Kaye
It is a great time to get pricing dialed in. Thank you for joining, Jasper. This was a fascinating breakdown of the KeyData Trends Report for 2026.

Jasper
Thanks for having me.

Kaye
Thanks for listening.

 

Eric Moeller hospitality CEO and STR leader