How to Personalize Emails Based on Guest Behavior & Preferences
Email Segmentation
You’ve probably heard the phrase “right message, right person, right time.” But let’s take it one step further: what if you could make every guest feel like your emails were written just for them?
That’s the magic of email segmentation—and it’s a total game-changer for vacation rental managers.
Instead of only sending the same message to your whole list, segmentation allows you to tailor emails based on guest behavior, preferences, and history. The result? Higher open rates, more engagement, and more direct bookings.
Let’s dig into what segmentation really is, why it matters, and how you can start using it to grow your business.
What Is Email Segmentation?
In simple terms, segmentation means dividing your email list into smaller groups based on specific criteria.
This could be:
How often someone travels
Where they’ve stayed
Whether they’ve booked before
Their location, preferences, or even birthday
Why bother? Because sending one-size-fits-all emails is like throwing spaghetti at the wall and hoping something sticks. Segmentation helps you send relevant emails that actually connect with your audience—and drive action.
Why Segmentation Matters for VRMs
Let’s face it: not all guests are the same. A repeat visitor who books every summer wants a different message than a brand-new lead who just downloaded your travel guide.
With segmentation, you can:
Send exclusive offers to VIP guests
Follow up differently with new leads vs. past guests
Recommend properties based on guest interests
Share content that’s actually helpful (not annoying)
This kind of personalization builds trust and loyalty—which means more bookings and better guest relationships.
Smart Ways to Segment Your Guest List
You don’t need a massive CRM or a PhD in data to get started. Here are some simple, high-impact ways to segment your list:
1. Past Guests vs. New Leads
Treat your warm leads like the gold they are.
For past guests:
Send “We Miss You” emails with exclusive offers
Highlight properties similar to the one they stayed in
Offer early access to seasonal booking dates
For new leads:
Start with value—local guides, what to expect, FAQs
Introduce your brand and build trust
Gradually move toward booking calls-to-action
2. Location-Based Segments
Where your guest lives can influence when and how they travel. For example:
Promote weekend getaways to drive-in markets
Highlight flight deals from major hubs
Share seasonal events or weather-based inspiration
A guest in Phoenix might be craving a cooler escape in the summer, while someone in Seattle might be itching for sunshine during the winter months.
3. Stay History or Property Preferences
If someone has stayed in a beach condo, don’t push your mountain cabin on them right away. Instead:
Recommend similar listings
Promote upgrades or new amenities at the same property
Offer loyalty discounts for returning to a favorite spot
You can also segment based on length of stay—weekenders vs. weeklong vacationers—and tailor your messages accordingly.
4. Engagement Behavior
Track how guests interact with your emails:
Opened but didn’t click? Try a different subject line or offer.
Clicked a property but didn’t book? Send a reminder with urgency.
Haven’t engaged in months? Consider a re-engagement campaign or remove them from your main list.
This ensures you’re not over-emailing the wrong people—and that your content stays relevant and welcome.
5. Booking Window or Travel Habits
Some guests book months in advance. Others love last-minute deals. Segment by booking behavior and send emails that match their travel rhythm:
Early bookers get seasonal previews and priority access
Spontaneous travelers get flash sales and last-minute availability alerts
Tools That Make It Easy
Most modern email platforms (like Mailchimp, ActiveCampaign, or ConvertKit) allow you to create segments with just a few clicks. Even basic tools often support tagging based on behavior or sign-up forms.
And if you're using property management or guest experience software, you may already have the data you need—it's just a matter of putting it to work.
The Bottom Line: Personalization = Profit
In a world where inboxes are crowded, segmentation helps your message stand out. It’s how you stop sounding like a business and start sounding like a host who truly knows and values their guests.
Segmented emails perform dramatically better than generic ones. Higher open rates, better click-throughs, and more conversions—all because you took a little time to know your guests better.
Start small. Pick one segment (like repeat guests or leads from your last campaign) and build from there.
