Email marketing helps you turn one-time guests into repeat bookings and referrals
Segmenting your audience and personalizing messages increases engagement and ROI
Automating key emails like welcome and rebooking offers saves time and improves guest experience
Booking calendars aren’t filling as fast as they used to. With guest acquisition costs rising and competition intensifying, relying on platforms alone to drive bookings is no longer sustainable. You need a direct line to your best guests, and email marketing gives you just that.
Done right, vacation rental email marketing becomes a high-leverage channel that brings past guests back, fills calendar gaps, and builds brand equity. It’s not about mass emails or promotions that go ignored. It’s about delivering the right message to the right guest at the right time—automatically.
This isn’t theory. Short-term rental managers who scale successfully use email not just to communicate, but to drive action. From automated welcome flows to post-checkout offers, each email becomes a tool to grow revenue and reduce dependency on booking platforms.
In this guide, we’ll break down five strategies that work for short term rental hosts, plus how you can get started building out an email list for long term success.
A strong vacation rental email marketing strategy starts with a clean, targeted list. Random contacts won’t fill your calendar, engaged guests who actually want to hear from you will. Think of your list as your guestbook. Every name should belong to someone who’s already booked or is seriously considering it.
No one signs up just to get another sales email. But offer a local restaurant guide, an events calendar with hidden gems, or a discount for returning guests? Now you’re giving them a reason to pay attention.
Travelers want more than a place to sleep. They want recommendations from someone who knows the area. A lead magnet like “3 Best Spots for Sunset Cocktails” will outperform a generic newsletter every time. Keep the tone friendly and helpful, and skip the hard pitch.
The goal isn’t to sell—it’s to help. Think like a host, not a marketer.
Guests who’ve already stayed with you are your best subscribers.
They know what to expect, and they’re more likely to come back. So ask for their email early—ideally before check-in. Use a welcome book to prompt them, or work it into your pre-arrival message.
If the booking came through Airbnb or another booking platform, you can still request an email—just be clear about why. Something like, “We’ll send you our local guide and a quick checkout checklist—drop your email here,” works well. It feels helpful, not pushy, and keeps the door open for future direct bookings.
Manage short-term rentals & bookings, message guests, take payment, and so much more. All in one easy-to-use platform (that never double-books).
No two guests expect the same experience and they won’t respond to the same message.
A family planning their annual beach trip wants different information than a business traveler dropping in midweek. Sorting your list based on guest behavior helps your emails feel intentional, not irrelevant.
Start by separating your contacts into clear groups based on how they travel. Repeat guests, first-timers, families, and business travelers all have specific needs and patterns. Returning guests often appreciate reminders about what made their last stay great. First-timers usually want more details about the property and nearby spots worth checking out.
Business travelers care about Wi-Fi speed, flexible check-in, and a quiet workspace. Families look for space, safety features, and extras like cribs or high chairs. When your message speaks directly to daily routines or trip goals, it feels useful instead of generic.
Here’s how to make your offers more relevant:
Repeat guests: Share early access to popular dates or a discount they won’t find on booking sites. A quick reminder of their favorite local café or hiking trail helps jog the memory.
First-timers: Offer a neighborhood cheat sheet, highlight top reviews, and make booking as simple as possible.
Business travelers: Focus on weekday availability, self-check-in, and a reliable workspace.
Families: Call out family-friendly features and kid-approved activities nearby.
When you send an email matters just as much as what it says. Use past booking data to send rebooking emails around the same time guests booked before.
If someone reserved a spring break week last March, reach out in early February. You’re not guessing—you’re catching them at the exact moment they’re making decisions.
Seasonal promotions work the same way. A winter guest who booked a mountain cabin? Reconnect in early fall with a cozy retreat offer before they start looking elsewhere.
Vacation rental email marketing works best when every message lands just when travel planning starts. Think of it as a helpful nudge, not a cold pitch.
Automation lets your emails work quietly in the background while you handle guests, vendors, and maintenance calls.
With the right setup, your guest communication stays consistent, timely, and helpful—without adding more to your plate. A few simple email flows cover the bulk of what guests need while opening the door to better reviews and return bookings.
Welcome email before check-in: Send this a few days ahead of arrival. Keep it friendly and clear. Include directions, parking details, and a few personal tips about the area—like your go-to coffee spot or a shortcut to the beach. Guests appreciate having everything in one place, especially when travel stress is high.
Thank-you or review request after check-out: Schedule this 24 to 48 hours after guests leave. Say thanks, ask how the stay went, and link directly to your review platform of choice. A short message that feels personal is often the nudge people need to leave feedback.
Rebooking offer or newsletter a few weeks later: Reach out after the trip glow fades but before the inbox swallows the memory. Mention something specific from the stay—a birthday celebration, a favorite restaurant—and offer a reason to come back. A private discount or early calendar access works well here.
Automated messages don’t have to sound like they were written by a robot. Use the guest’s name. Mention the dates they stayed. If they brought a pet or stayed for an anniversary, reference it. Small details make the message feel like it came from someone who actually paid attention.
Even with templates, you can write like a person and not a policy manual. Skip “valued guest” and “please be advised.” Write like you’re texting a friend and be clear, helpful, and direct.
It’s simple to automate repetitive tasks with Uplisting's short-term rental software. You’ll save hours every week and eliminate human error. Go ahead — take some time off.
Every time a past guest comes back through your direct site, you keep more revenue and avoid platform fees. The inbox is where you build loyalty and repeat stays—without the expensive middlemen.
Guests won’t book directly just because they can. They need a reason to skip the platform they used last time. Start with small perks that feel personal—ones you’d appreciate as a traveler.
Offer a discount for returning guests: Even 5–10% off makes direct booking feel like a reward, not a hassle.
Add early check-in or late checkout: High value, no extra cost if your schedule allows.
Send a shareable referral code: If their friend books, both get a bonus. You grow your audience without spending on ads.
When you pair these extras with a well-timed email, they outperform any generic promotion sitting on a listing page.
Once someone clicks your link, the experience needs to match the promise.
Direct booking sites should load fast, work on mobile, and reflect the same care you put into your guest experience. If the site feels clunky or inconsistent with your emails, trust erodes fast.
Vacation rental email marketing isn’t just about sending property photos and updates. It’s about building a relationship that encourages guests to return—on terms that work better for you. Every email is a chance to shift behavior from platform-first to direct-first.
Guessing what works in vacation rental email marketing usually leads to missed bookings and frustrated guests.
Instead of relying on hunches, let the numbers show what’s connecting—and what isn’t.
Start with the numbers that matter: open rate, click-through rate, and booking conversion. If open rates are weak, the subject line didn’t pull its weight. If clicks stay low, the message didn’t hit home. When clicks go up but bookings stall, the offer or landing page needs work.
Try A/B testing one variable at a time. Compare a casual subject line to a more direct version. Swap one image for another. Experiment with offer timing. Every test tells you something useful, even if the results aren’t what you hoped for.
Break results down by guest type. Returning guests, business travelers, and families respond differently. A discount for weekday stays may work well for work trips, but not for school holidays. Watch the trends in each group to figure out where to focus next.
Sending emails too often turns interest into annoyance fast.
One thoughtful message with clear value gets more traction than a flood of reminders. If inboxes feel crowded, people stop reading—or unsubscribe altogether.
When open rates drop or unsubscribes climb, the message likely arrived too late, too often, or with too little to offer. Pull back and focus on timing and relevance instead of volume.
Some of the largest short-term rental operators (with 250+ properties) rely on Uplisting's software to scale their businesses.
Marketing your short term rental doesn’t need to feel like another job you didn’t sign up for.
You don’t need a creative team or a polished brand to send emails that bring people back. If you’re managing multiple properties, the right setup helps you stay connected with past guests—and fill your calendar—without adding more to your plate.
Combined with strong calls to action and ongoing performance tracking, these five strategies help you turn every guest interaction into a long-term opportunity. When done consistently, email becomes more than communication—it becomes a growth channel you control.
Ready to take the next step? Sign up for Uplisting to streamline your vacation rental management and put your email marketing—and your entire operation—on autopilot.
Yes, but timing matters. You can ask after the booking is confirmed—usually through the welcome message, check-in instructions, or a friendly follow-up. Let guests know what they’ll get in return, like a local guide or helpful tips about the stay.
Mailchimp, ActiveCampaign, and ConvertKit are all reliable options. The right choice depends on how many listings you manage and which tools already handle bookings and automation. Look for a platform that syncs easily with your system and supports workflows like guest segmentation and scheduled campaigns.
Aim for every one to two months. That’s often enough to stay relevant without turning into noise. If you run seasonal offers, promote high-demand weekends, or want to fill calendar gaps, bump up frequency—but only when you have something specific to share.
Yes. Even with one listing, vacation rental email marketing helps keep more control over bookings and build stronger guest relationships. A single well-written message can lead to a repeat stay without paying commission or relying on a platform algorithm.
Send guest-focused content they actually want to read. Share local recommendations, limited-time offers, or early access to high-demand dates. When messages are helpful, guests don’t mind seeing your name in their inbox—and they’re more likely to book again.
Yes—platforms like Mailchimp and ActiveCampaign support features tailored for operators managing multiple listings. You can sort contacts by stay history, property, or guest type, then send targeted messages without juggling separate lists or starting from scratch each time.
We’ve built an all-in-one property, channel management and automation tool to help property managers scale seamlessly.
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