I’m pulling back the curtain on something a lot of short-term rental hosts are quietly experiencing right now — calendars that feel a little more open than we’d like.

Instead of panicking, I’m walking through exactly how I’m analyzing the numbers, evaluating pricing strategy, and digging into market data to understand what’s really happening. From dynamic pricing tools like PriceLabs to reviewing comps and optimizing listings, this episode is a real-time look at the behind-the-scenes decisions hosts have to make when bookings slow down.

If you’re a short-term rental owner who wants to understand how pricing strategy actually works — and how to respond strategically when bookings aren’t where you want them to be — this episode will give you a practical framework for navigating it.

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Why This Year Feels Different for Short-Term Rental Hosts

We’ve been hosting since 2019 across three different states — North Carolina, Kentucky, and now Virginia.

And honestly?

This has been the slowest booking season I’ve personally experienced.

Now, part of that may be because Luna is a brand-new property, so we’re still learning the seasonality of this market. But even our Kentucky property, which has been established longer, is showing slightly different booking patterns this year.

So instead of immediately assuming something is wrong, I started doing what every host should do in this situation:

Look at the data.

Because when your calendar isn’t full, the worst thing you can do is react emotionally.

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What Is Dynamic Pricing?

Dynamic pricing simply means adjusting your nightly rate based on real-time demand and market conditions instead of using one fixed nightly price year-round.

Factors that affect dynamic pricing include:

• Seasonal demand
• Local events and holidays
• Competitor pricing
• Booking trends in your market
• Your listing’s occupancy rate

When we first started hosting, I was technically doing a very basic version of dynamic pricing — raising prices in summer and lowering them in off-season.

But last year at the Level Up Your Listing Summit, I was introduced to PriceLabs, which automates much of this process.

Dynamic pricing tools analyze market data and automatically adjust your nightly rate to match demand — helping you avoid both underpricing and overpricing your listing.

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The Three Most Important Pricing Numbers

Inside PriceLabs, every listing revolves around three core numbers:

1. Base Price

Your base price is your starting point.

This is determined by:

• Comparable listings in your market
• Property size and layout
• Amenities
• Design quality
• Guest experience

However, if your property is unique, comps can sometimes be misleading. Two homes might have the same bed/bath count but completely different design, branding, and guest appeal.

So always review comps manually before relying entirely on automated pricing suggestions.

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2. Minimum Price

Your minimum price protects your profitability.

This ensures you never drop below a nightly rate that actually makes financial sense for your property.

When calendars feel empty, many hosts panic and drop prices dramatically. But that often leads to:

• Lower-quality guests
• Higher wear and tear
• Reduced profitability

Your minimum price acts as a safeguard against emotional pricing decisions.

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3. Maximum Price

Your maximum price caps the highest nightly rate the system can set.

Even though dynamic pricing software is smart, I still like setting a maximum just to ensure prices don’t accidentally spike beyond what the market will realistically pay.

The exception?
Special events.

For example, our Kentucky property can exceed our maximum during Kentucky Derby weekend, where demand justifies significantly higher pricing.

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Advanced Pricing Strategies Hosts Should Know

Dynamic pricing tools also allow you to create more advanced strategies.

Here are a few I regularly use.

Far-Out Pricing

If someone books far in advance — for example 90 days out — you can charge a higher nightly rate.

Why?

Because planners often prioritize securing the dates over finding the cheapest option.

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Last-Minute Pricing

On the opposite end of the spectrum, you can gradually lower prices as a date approaches.

For example:

• 30 days out → standard pricing
• 14 days out → slight reduction
• 7 days out → further reduction

This helps fill remaining dates without sacrificing revenue too early.

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Orphan Day Pricing

Orphan days are small gaps between bookings that can’t normally be reserved due to your minimum stay requirements.

Example:

If you require a 3-night minimum, but a booking leaves a 2-night gap, those nights typically go unbooked.

Orphan day pricing allows you to:

• Reduce the minimum stay for those specific dates
• Fill gaps in your calendar
• Increase total occupancy

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Using Market Data to Compare Your Listing

One of my favorite PriceLabs features is the Neighborhood Data tool, which lets you view nearby comps on a map.

Looking at Luna’s comps revealed several interesting insights:

Competitor nightly rates

Our minimum nightly rate: $165
Nearby rustic cabin: $104

That’s a significant difference.

However, their property is far less designed and offers fewer amenities, so we still need to weigh positioning vs. pricing.

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Minimum stay requirements

Many competitors allow one-night weekday stays, while we require two nights.

Adjusting weekday minimums may help increase occupancy without sacrificing prime weekend bookings.

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Cleaning fees

Our cleaning fee: $125

Nearby listings ranged from $30–$100.

This pricing difference could affect booking decisions when guests compare listings side-by-side.

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A Hidden Factor: Airbnb Service Fees

Another interesting discovery while reviewing comps was the service fee structure.

Some listings operate under Airbnb’s split fee model:

• Host pays ~3%
• Guest pays ~12.5%

Others — like ours — use a PMS system (Property Management System) such as Lodgify.

This converts the listing to a host-only fee model:

• Host pays ~15.5%

Listings using host-only fees often rely on direct booking websites or multiple platforms like VRBO, but it’s possible Airbnb’s algorithm slightly favors listings fully hosted within their ecosystem.

This is something many hosts are actively watching right now.

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When Your Calendar Isn’t Full: What Not to Do

If your bookings feel slow, here’s what I don’t recommend doing.

– Panic
– Slash prices dramatically
– Assume your listing is failing

Instead, use open calendar space as data.

Ask questions like:

• Is the entire market slow?
• Are my comps booking faster than I am?
• Are my prices aligned with the market?
• Does my listing accurately represent my property?

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Using AI to Optimize Your Listing

Recently I tested a new PriceLabs feature called Listing Optimizer.

This AI tool scans your listing and provides improvement suggestions.

Some insights it caught on our Luna listing included:

• Our best photos weren’t in the top five images
• Some amenities listed did not have photos attached
• Our listing title contained characters Airbnb doesn’t recognize
• Certain features (like our stargazing dome) weren’t visually represented

These small adjustments can directly affect how Airbnb ranks your listing.

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Why Listing Accuracy Matters

One important takeaway from the listing optimizer:

If your listing says you offer an amenity but there’s no photo showing it, Airbnb may treat that as a trust issue.

In our case:

• We listed a grill
• We listed a stargazing dome

But neither had photos yet because the outdoor areas weren’t fully staged.

The algorithm flagged this mismatch.

Even though our intentions were good, the system interpreted it as a potential discrepancy.

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Another Tool Hosts Should Use: AirDNA

While PriceLabs helps with pricing, AirDNA helps with broader market research.

AirDNA aggregates data across Airbnb listings and provides insights like:

• Average nightly rate
• Market occupancy
• Revenue potential
• Seasonal demand patterns

There’s both a free and paid version, and it’s incredibly useful when evaluating a new market or troubleshooting an existing listing.

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If 2026 feels a little different for your short-term rental business, you’re not alone.

Even experienced hosts are seeing shifts in booking patterns.

But instead of reacting emotionally, this is the moment to:

• Review pricing strategy
• Analyze market data
• Optimize your listing
• Make strategic adjustments

The hosts who succeed long term aren’t the ones who panic — they’re the ones who pay attention to the numbers.

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Want a Market Report for Your Area?

If you’re considering purchasing a short-term rental — or want to compare your listing performance with your local market — I’d be happy to run a quick AirDNA market report for you.

Just DM me the word REPORT on Instagram at @brandandmarket.co, and my automation will walk you through submitting your city and state. I’ll send back a quick video breakdown of what the market data looks like in your area.

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🎧 Listen to the full episode:
Brand & Market Podcast – Episode 90

If this episode was helpful, please consider rating and reviewing the podcast so more hosts can find it.

And as always — I’m cheering you on as you build the best brand in your market.