How to Win Direct Bookings from Event Travelers
—Even Against Airbnb and Vrbo
Last year during our city’s marathon weekend, every short-term rental in the area sold out—except one.
The host had great reviews. A beautiful place. But they were only listed on Airbnb and didn’t realize the event was happening until guests stopped messaging.
Meanwhile, two other hosts I work with? They were booked solid six weeks in advance, all through direct bookings.
One even had a waitlist.
The difference?
A little planning. A direct booking strategy. And just enough personalization to make guests say, “This is exactly what I need.”
7 Smart Ways to Compete With OTAs—And Win
1. Build Your Local Event Calendar
Create a simple spreadsheet of events in your area 3–6 months out. Include major tourism draws and niche happenings.
Examples:
Bluegrass Festival – July 12–14
City Marathon – Sept 8
Fall Craft Fair – Oct 5
Fishing Season Opener – May 1
🛠️ Use tools like ChatGPT or Perplexity AI to uncover overlooked events and seasonal trends in your region. Old skewl tip, check the chamber of commerce or tourism website for their calendar of events.
2. Promote Events Before the Platforms Do
Update your Google Business Profile with posts, photos, and offers tied to upcoming events. Share quick updates across your site, socials, and email list.
📌 SEO Tip: Include keywords like “festival lodging,” “vacation rental near [event],” and “direct bookings in [location].”
Visual idea: Screenshot of a festival landing page or a Google post highlighting a limited-time special.
3. Use AI to Market Like a Pro
Even if you’re not a marketer, you can create high-converting content quickly.
AI tools help with:
Personalized guest messaging
Blog posts or emails for event-driven travel
Social media captions
Creating dynamic pricing around peak demand periods
4. Create Direct-Only Perks (With Real Value + Urgency)
Give guests a reason to skip the OTAs—and make them act fast.
🎁 Popular perks:
Early check-in or late checkout
Free room upgrade (when available)
Book 3 nights, get the 4th free
Event-themed welcome kits (festival snacks, runner's breakfast, etc.)
Local partner discounts (restaurant, spa, tour guide)
Loyalty discounts for repeat guests
Early-bird specials: “Book by July 1 and save”
Urgency matters—try “Only 5 spots available” or “Offer ends Sunday.”
5. Personalize for Niche Travelers
Tailor your messaging and amenities to the event’s audience.
🏃 Marathon weekend: early breakfast, energy snacks, foam rollers
🎶 Festival stay: sunscreen, snacks, late checkout
🎣 Fishing trip: early morning coffee, freezer access, drying rack
Ask guests about their plans when they book—even a simple “What brings you to town?” in your confirmation email can help you tailor a welcome kit, guidebook, or local recs.
Guests are more likely to remember—and return for—the thoughtful touches tailored to their event experience.
6. Keep Your Brand Name Consistent
Event-driven travel often starts on an OTA... but guests will Google you to book direct.
✅ Use the same property name across:
Your website
Airbnb/Vrbo
Google Business
Social media
Your email signature
Make it seamless for guests to find and trust you.
7. Make Sure Your Site Converts
You can do everything right—but if your site doesn’t work, you’ll lose the booking.
✅ Your booking engine should be:
Fast and mobile-friendly
Secure and easy to navigate
Clear about pricing and availability
Optimized with event-specific offers or FAQs
📸 Visual idea: Example of a direct booking page with a “Festival Weekend Package” clearly promoted.
📘 Free Resource: VR Local Event Marketing
Micro-Case Study: Todd Parker’s $100K Direct Booking Success
Todd Parker manages several cozy cabins in the Smoky Mountains (Tennessee) and Blue Ridge Mountains (Georgia). By leaning into direct bookings, he generated over $100,000 in revenue—without relying on Airbnb or Vrbo.
His site, overlookcabinrentals.com, made it easy for guests to see the value:
✅ No booking fees
✅ Transparent pricing
✅ Trust-building messaging (“Book direct, save more”)
✅ Side-by-side comparison with OTA rates
“When guests compare Airbnb or Vrbo to our direct booking, they see there are no booking fees, no extra hidden service charges, and they appreciate that.”
Todd’s approach didn’t just increase revenue—it changed his lifestyle.
He gained more control over guest communication, built stronger relationships, and saw a boost in repeat stays and referrals.
💬 What struck me most about Todd’s results?
It wasn’t just the $100K—it was how simplified, repeatable, and personal his process became. Direct booking gave him freedom and focus, not just better margins.
🔁 Final Thought
OTAs are helpful for visibility.
But if you want stronger guest relationships and a sustainable business, direct booking is the long game.
You don’t need to do everything—just be more intentional.
Plan ahead. Personalize the guest experience. And use AI to simplify your strategy without sacrificing your time.
What About You?
What’s your next big event?
Have you tried any of these strategies?
👇 Share your story below or hit reply—I read every message.
📩 Know a host who could use these tips? Forward this post!
About the Author
Hi, I’m Kay—founder of Smart Pineapple and a lifelong hospitality nerd who believes small properties deserve big opportunities. I started one of Mexico’s first online travel platforms back in the 90s, and I’ve been helping vacation rentals, boutique hotels, and tourism brands grow ever since.
Here on Substack, I share practical strategies, simple tech tips, and honest stories about what it really takes to stand out, get booked, and build a business you actually enjoy running.
Got a question or want me to cover something specific? I’d love to hear from you. Drop me a note at kay@smartpineapple.ai or swing by smartpineapple.ai.
Connect with me on Linkedin
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References:
1 Lodgify: Writing a Great Vacation Rental Newsletter
2 Corsica Megan Castor: Vacation Rental Newsletter Ideas
3 Erica Drayton Substack Guide
4 Forbes: The Rebirth of Newsletters
5 BuildUp Bookings: Vacation Rental Copywriting Tips
6 Tim Denning: Substack Success