Master Direct Bookings: Stop Leaving Money on the Table
Make this the month you start bringing in more bookings direct.
Still letting Airbnb or VRBO take a cut of every booking?
Between guest service fees and host commissions, many bookings lose 15–20% to the platforms—sometimes more. But you don’t need to keep playing someone else’s game.
This week, we’re diving into the direct booking strategies top-performing hosts are using to fill their calendars before the platforms catch on. If you want more control, better margins, and long-term growth, this is your playbook.
Inside This Issue:
✅ Your 7-Step Direct Booking Strategy
✅Real Case Study: $100K+ booked direct
✅ Free Resource: “Local Event Marketing” eBook
✅ Prompt of the Day: Build your custom event calendar in 30 seconds
Direct Bookings That Work
Stop feeding platforms. Start building a business.
Here’s the math:
Airbnb takes up to 17% per booking when you combine host and guest fees (sometimes even 16% host-only)
VRBO charges around 8%, or a flat annual fee
→ Either way, that’s money you could be keeping with a direct booking strategy.
The most profitable hosts? They’re planning around local events, offering real incentives, and building a direct relationship with guests that pays off for years.
Let’s break it down:
✅ Your 7-Step Direct Booking Strategy
1️⃣ Build Your Local Event Calendar
Start with a simple spreadsheet of events 3–6 months out:
marathons, food festivals, fishing openers, wine walks—anything that draws visitors.
→ Pro Tip: Use ChatGPT to surface lesser-known events in your area.
2️⃣ Be First, Not Last
Post event-specific content on your Google Business Profile, blog, and social media before Airbnb listings catch on.
Use search-friendly phrases like:
“Vacation rental near [Event Name]”
“Lodging for [Festival] in [City]”
3️⃣ Let AI Do the Heavy Lifting
Use AI to create:
Guest message templates
Blog content and social captions tied to events
Dynamic pricing strategies that auto-adjust for demand
You stay focused on hosting—let AI handle the marketing engine.
4️⃣ Create Direct-Only Perks That Matter
Make booking direct irresistible:
Book 3 nights, get the 4th free
Event-themed welcome kits (runner’s breakfast, festival snacks)
Early check-in or late checkout
Local discounts
Time-sensitive promos: “Only 5 spots left. Offer ends Sunday.”
5️⃣ Personalize the Stay
Tailor your offerings to guest type:
Marathon guests: Foam rollers, protein bars, early breakfast
Festivalgoers: Sunscreen, recovery snacks, late checkout
Anglers: Freezer access, coffee at dawn, gear drying station
→ Ask: “What brings you to town?” during booking—and deliver accordingly.
6️⃣ Keep Your Brand Consistent
Use the same name, logo, and voice across:
Your website
Airbnb/VRBO listings
Google Business Profile
Social media
Consistency builds trust. Trust drives bookings.
7️⃣ Make Your Website Convert
Ensure your booking site is:
✅ Fast
✅ Mobile-friendly
✅ Optimized for seasonal keywords
✅ Easy to use and secure
Consider tools like Hospitable, Uplisting, or Hostfully to streamline the process.
💼 Real Results: The $100K+ Case Study
Todd Parker manages vacation cabins in the Smoky Mountains. By building a professional direct booking site and planning around local events, he brought in over $100,000 in direct bookings using Hospitable’s platform.
His key moves:
Clear communication of savings (no platform fees or hidden charges)
Event-targeted content
A frictionless booking experience
👉 Transparency sells—and direct saves.
📖 Free Resource of the Week
🎁 Local Event Marketing: Turn Events into Bookings
This free Smart Pineapple eBook shows you how to:
Find high-impact local events year-round
Plan seasonal strategies to fill gaps
Use AI + dynamic pricing to stay competitive
Event Goldmine Prompt
Want to find hidden-gem events that drive bookings? Let AI do the research for you.
Here’s how:
1. Open Your AI Tool of Choice
Pick your favorite. Any of these will work:
ChatGPT by OpenAI → chat.openai.com
Gemini by Google → gemini.google.com
Claude by Anthropic → claude.ai
Or use whichever AI you prefer.
2. Copy and Paste This Prompt
Fill in the brackets with your city, timeframe, and guest type.
“List [X] lesser-known or niche events in [city or region] happening in the next [timeframe] that are likely to attract [target audience type] but are not widely promoted on Airbnb, OTAs, or major tourism channels. Prioritize events that align with [themes like food, music, outdoor recreation, cultural festivals, etc.].
For each event, provide:
Event Name
Dates
Event Type (e.g., art walk, indie concert, local sports tournament)
Why it appeals to [target audience]
Estimated size, visibility, or travel draw (if known)
(Optional: Notable nearby attractions or lodging demand insights)
Format the results as a clean, easy-to-scan list.
Pro Tip: Save your favorite prompt versions in a doc or Notes app. You can reuse them monthly as your event calendar updates.
Try These Prompt Variations
Tailor the prompt to fit your property, your audience, or the season:
By Traveler Type:
“...that appeal to digital nomads / remote workers / traveling nurses / families with kids”By Booking Window:
“...happening in the next 45 days”
“...scheduled 3–6 months from now to plan ahead”By Niche Event Type:
“...centered around food trucks, craft beer, outdoor fitness, or art markets”By Neighborhood Focus:
“...within 10 miles of [neighborhood or attraction] to attract local event-goers”By Season:
“...perfect for off-season travel or shoulder season experiences”
Use variations to uncover booking opportunities your competitors are ignoring.
💬 When Words Hit Home
Sometimes, a client puts into words exactly what we strive for: to support with clarity, empathy, and action.
This message from Brian Montgomery reminded us why we do what we do.
Here’s a glimpse that says a lot—and the rest, well, you’ll want to read it yourself.
👉 Read the full review
🍍 Final Thought from Me
Here’s the deal: you don’t need to do everything to start winning at direct bookings—you just need to do the right things. One event. One strategy. One move that puts you in control.
If you want help spotting those moves (the ones that actually make a difference), I open up a handful of strategy sessions each month for hosts who are serious about growing smarter—not just bigger.
📅 Snag a spot on my calendar before they’re gone:
👉 [My calendar]
This is where the good stuff happens—clarity, strategy, and maybe a little tough love if you need it 😉
Talk soon,
Kay 🍍
P.S. If you uncover a weird local event using the AI prompt (goat yoga, pie festival, you name it), please tell me. I collect these now.