Episode 634

Listener Q&A: Mastering Airbnb Pricing, Photo Tours & Last-Minute Bookings

August 6, 2025 Jasper Ribbers
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In this episode of Get Paid For Your Pad, Jasper Ribbers (Co-founder of Freewyld) broadcasts from Savannah, Georgia, where he’s visiting a revenue manager. He kicks off the episode with updates from the field before diving into key revenue management questions submitted by listeners.

If you’ve ever been confused about Airbnb’s photo tour functionality, dynamic pricing tools, or how to set last-minute rates, this episode delivers practical, data-driven strategies that will help you master pricing and listing optimization.

You’ll hear:

  • Why Airbnb’s Photo Tour is misunderstood, and how to keep control over your top 5 images
  • How to structure your photos to boost conversion using space-based sorting
  • The difference between full sync and limited sync when using PMS platforms like Guesty
  • How Jasper approaches dynamic pricing and why manual overrides still matter
  • The most effective way to manage last-minute pricing (without killing your weekends)
  • How Jasper uses occupancy pacing, minimum night rules, and orphan gap logic to maximize revenue

We also talk about:

  • Common mistakes with pricing tools like PriceLabs and how to avoid them
  • Why most “bad pricing” issues are actually “bad settings”
  • The benefits of using group-level or account-level overrides to save time
  • Jasper’s analogy of pricing tools as a car (you still have to drive it!)

🎯 Mentioned in the Episode:

  • Freewyld Foundry: Airbnb Listing Optimization Checklist - A free 18-page PDF packed with expert tips (no email required)
  • PriceLabs - Dynamic pricing tool for STR operators
  • Guesty - PMS with full and limited sync modes that impact Airbnb functionality

💡 Key Pro Tips from Jasper:

  • Set a minimum weekend rate to avoid discounting high-demand days
  • Use occupancy-based rules instead of relying solely on last-minute pricing factors
  • Use custom coupons and old-fashioned surveys to track attribution of direct bookings
  • Think of your pricing tool as a race car, you still have to steer

📍 Want Jasper to answer your question on the podcast? Email him at jasper@freewyld.com.

Whether you’re struggling with pricing automation, photo strategies, or just want to improve your Airbnb revenue management game, this episode is a must-listen for every STR operator who wants to stay ahead.

Jasper Ribbers:

Welcome back to Get Paid For Your Pad. I'm currently in Savannah, Georgia, visiting Thomas, one of our revenue managers. It's my first time here and it's a great experience. The weather is beautiful, the people are friendly, and the historic vibe of the city is impressive. We’re even planning to go kayaking this weekend.

Thomas has been doing fantastic work for our clients, building systems, coming up with ideas, and delivering strong results. It’s always a pleasure to meet our remote team in person.

Since relaunching the podcast with two episodes per week, I’ve received a bunch of listener questions, some via email, others as YouTube comments. Today, I’m answering four of the most common ones. If you ever want to submit your own, email me at jasper@freewyld.com.

  1. Should You Use Airbnb’s Photo Tour Functionality?

There’s a lot of confusion about Airbnb’s photo tour feature. Some hosts avoid it because they think it removes control over the first five photos. That’s not entirely true.

You still have control over the first five images. While the photo tour reorders images by room after clicking into a listing, you can drag and drop the initial five on the backend. Just go to your listing, click "All Photos," and rearrange them.

Why use Photo Tour at all? Two reasons:

  • It improves user experience. Guests can view photos room by room and see associated amenities, making navigation intuitive.

  • Airbnb tends to reward hosts who adopt new features. Listings using all available tools usually rank higher in search.

So yes, use Photo Tour, just manage the first five photos carefully.

  1. PMS Sync Issues with Photo Tour

Many hosts report that their PMS undoes their photo tour setup. This varies by platform. For example, Hostfully allows correct syncing if set up properly. But yes, there’s a learning curve.

My advice: start with one listing. Figure out the correct setup process with your PMS, then apply it to others.

A note for Guesty users, be aware of the difference between Full Sync and Limited Sync. If you're on Full Sync, Guesty will override your Airbnb changes. Limited Sync gives you full control over Airbnb’s photo layout.

  1. Why You Should Still Use a Pricing Tool (Even in Small Markets)

Some hosts worry that dynamic pricing tools like PriceLabs don’t work in smaller markets. That’s a misconception.

Tools like PriceLabs expand their data set geographically when there’s limited local supply. Even if your market is small, they’ll gather enough comps from nearby areas.

Even if you're not confident in the price recommendations, you can use pricing tools for:

  • Dynamic minimum night rules

  • Gap logic to fill orphan days

  • Adjacency booking incentives

You can even override prices manually within the tool if needed. It’s still far more efficient than setting prices directly in Airbnb or your PMS.

  1. Managing Peak Pricing with Precision

For events like college football games, PriceLabs sometimes sets prices extremely high, too high to convert. In one case, we saw bookings listed at $4,000 due to a system safety cap.

Here’s what we do: look at the highest ADR historically booked for that property and add a reasonable premium (e.g., $300 higher). Then we set that as the max price so the algorithm can adjust downward as the date approaches.

That gives us dynamic pricing with guardrails.

  1. How to Automate Last-Minute Discounts (Without Tanking Weekend Rates)

Last-minute pricing is tricky. If you lower prices too aggressively, weekends get undervalued.

Solutions:

  • Use the Occupancy-Based Adjustments feature to discount weekdays without affecting weekends.

  • Set a minimum weekend price so the system never drops below that threshold.

If you need to do overrides, do them at the group or account level, never listing by listing. It saves hours.

For example: set a 90% discount for weekdays 0–7 days out to hit your $99 minimum, while setting the weekend minimum at $149. That way, your strategy remains consistent without daily manual adjustments.

Final Tip:

If your tool is giving bad prices, it's likely a settings issue. Adjust demand sensitivity or seasonality to get more accurate results. These tools don’t “guess”, they follow your rules.

Free Resource:

Want to make sure your listings are fully optimized? Download our Airbnb Listing Optimization Checklist. No email required. It includes the most commonly missed opportunities and links to request Airbnb categories.

Thanks for tuning in. I’ll be back next week with more insights. And if you’re ever in Savannah, go check out those container ships, they’re incredible!