The Guest Booking Journey (5 Steps)
Understanding When and How to Email Guests for Maximum Impact
If you’re managing vacation rentals, you already know timing is everything. Whether it’s updating your calendar before peak season or responding to an inquiry ASAP, the right action at the right time makes all the difference.
Email marketing is no exception.
You might already be sold on the idea of email as a powerful direct booking tool (and if not, go read this and this—you’ll be convinced!). But now it’s time to dig deeper and get strategic: when should you email your guests, and what should you say to make the most impact?
Because sending the right email at the wrong time? That’s a missed opportunity. But send the right message at just the right moment—and boom: that’s how you fill your calendar and build guest loyalty.
Let’s break down the guest booking journey and where email fits in at each step.
Step 1: The Discovery Phase
This is the dreaming stage—guests are browsing, fantasizing, and maybe even comparing properties across OTAs.
Email Opportunity: Lead Capture + Nurture
You probably won’t get a direct booking yet—but you can collect their email and stay in touch. Offer something of value to grab their attention:
A free local guide or travel checklist
Early access to dates before they go live on Airbnb
A small discount code for booking direct
Set up an automated welcome series for new subscribers to introduce your brand, highlight your top properties, and build trust. This is your chance to guide them toward a direct booking—before they even realize they were going to.
Step 2: The Consideration Phase
Now they’re serious. They’ve narrowed it down and are looking at specifics—availability, price, amenities.
Email Opportunity: Personalized Follow-Ups
If someone filled out a form, clicked a booking link but didn’t complete, or even just opened multiple emails… reach out. A well-timed message can nudge them forward:
“Hey [First Name], still thinking about your [Location] getaway?”
“We noticed you were checking out [Property Name]. Great news—it’s still available!”
Don’t underestimate the power of a simple, personal reminder. This is when they’re closest to booking. Be there.
Step 3: The Booking Phase
They’ve made the leap—congrats! But your work isn’t done yet.
Email Opportunity: Confirmation + Pre-Arrival
Send a warm, branded confirmation email right away. Then, schedule follow-ups that:
Answer FAQs
Share packing tips or must-do local activities
Offer add-ons like early check-in or local partnerships
You’re setting expectations and building anticipation, which leads to happier guests—and better reviews.
Step 4: During the Stay
Yes, email still matters even after they check in.
Email Opportunity: On-Site Touchpoint
A quick message mid-stay makes guests feel cared for:
“Hope your stay is going great! Need anything? We’re just a click away.”
Bonus: include a link to leave feedback or a referral incentive they can share.
It shows you’re proactive, which can help resolve issues before they turn into bad reviews.
Step 5: Post-Stay
This is your golden window. They’ve had the experience—they’re warm, familiar, and (hopefully) happy.
Email Opportunity: Thank You + Rebook
Within a few days of checkout, send a thank-you note with:
A personalized message and photo from their property
A discount code for their next stay
A request for a review or referral
Then, add them to a nurture list with occasional emails: birthday deals, seasonal promos, “We miss you” notes, or invites to new listings.
Keep them in the loop without overwhelming their inbox. This is where long-term loyalty is built.
Timing Matters—But So Does Relevance
Sending the right email at the right time is powerful. But to really make an impact, make sure your content matches their mindset.
A guest who just booked doesn’t need a “Book Now” button. They need details, reassurance, and a great experience.
A past guest doesn’t want general fluff—they want a warm message that says, “Hey [First Name], we remember you—and we’d love to host you again.”
Automation tools make this easy, but the real magic comes from intentionality: putting yourself in the guest’s shoes and crafting messages they’ll actually appreciate.
The Bottom Line: Map the Journey, Maximize the Impact
Your guests go through predictable phases—and your emails should, too. By aligning your messages with the guest booking journey, you create a smoother, more engaging experience that leads to more direct bookings and repeat guests.
So don’t just email when you have a sale. Email with purpose, with timing, and with the guest experience in mind.
