Most vacation rental operators focus on filling their calendars with new bookings. But what if the secret to sustainable growth isn’t finding more guests—it’s bringing back the ones you already have?
Repeat bookings email marketing is the most overlooked revenue driver in the short-term rental industry. While you’re spending time and money acquiring new guests through online travel agencies, your past guests are booking their next vacation somewhere else. The solution? A systematic email strategy that keeps you top of mind and makes rebooking effortless.
Why Guest Retention Matters More Than You Think 💡
Consider this: a guest who books your property once for $2,000 seems valuable. But a guest who books three more times over the following years? That’s an $8,000 customer. This concept—guest lifetime value—transforms how you should think about marketing.
Beyond the obvious financial benefits, focusing on repeat bookings email marketing delivers three critical advantages:
Increased profit margins 💰. Direct bookings eliminate platform fees that can eat up 15-20% of your revenue. You keep more money, and guests often save too—creating a genuine win-win situation.
Brand loyalty and relationships 🤝. When you communicate directly with guests, you build a connection that transcends a simple transaction. You become their trusted accommodation partner for that destination, not just another listing in a sea of options.
Business resilience 🛡️. Relying solely on third-party platforms puts your business at risk. Account suspensions happen. Algorithms change. Diversifying your booking sources protects your revenue stream and gives you control over your business destiny.
The Foundation: Build Your Email List First 📧
Before you can implement any repeat bookings email marketing strategy, you need email addresses. This seems obvious, but many operators miss a crucial opportunity: collecting multiple emails per reservation.
Think about it—a six-bedroom property that sleeps twelve people represents one booking but potentially twelve email addresses. Each person in that group is a potential future guest who might book for their own family trip, work retreat, or friend gathering.
Tools like Stay Fi and similar Wi-Fi-based collection systems automate this process. Guests connect to your wifi, opt into communications, and you’ve instantly expanded your reach. If you’re collecting emails manually, make it part of your welcome process and follow proper consent protocols.
The key is starting now ⏰. Even if you’re not ready to launch email campaigns, begin building your list today. Future you will thank present you.
Email Sequences vs. Campaigns: Know the Difference 🔄
Successful repeat bookings email marketing uses two distinct approaches, and understanding the difference is critical.
Automated sequences (also called workflows or flows) are evergreen email series triggered by specific actions—typically when a guest checks out. Once set up, they run automatically without any manual effort. A guest checks out on Tuesday, and your sequence begins sending value-driven emails over the next 200-365 days.
Campaigns are one-time broadcasts sent to your entire list for time-sensitive opportunities—a last-minute opening, a local event like a festival or race, or seasonal promotions. These require manual creation and scheduling but serve specific strategic purposes.
Most operators should invest 80% of their email marketing energy into building solid automated sequences, with occasional campaigns for special situations.
What Makes an Effective Email Sequence? ✨
The most common mistake in repeat bookings email marketing is leading with discounts. Sending “10% off your next stay!” every few weeks trains guests to expect deals and attracts price-sensitive customers who aren’t your ideal repeat bookers.
Instead, focus on value-first content that triggers emotional connections to their experience.
Your sequence might look like this:
📅 Days 1-2 after checkout: Thank you message with direct booking information
🎁 Days 3-5: Limited-time direct booking incentive (if you choose to offer one)
💭 Day 30: “Can you believe it’s been a month?” nostalgic message with local updates
🗺️ Day 60: Insider tips they missed—hidden gems locals know about
❤️ Day 90: Personal story about why that destination is special to you
🍂 Day 120: Seasonal preview of what’s coming up
📆 Day 180: Gentle reminder about rebooking for next year
Notice how only one email directly pushes a discount. The rest provide value, trigger memories, and maintain connection. This approach attracts quality guests who choose you for the experience, not the price.
Keep emails conversational and personal—plain text format, signed with real names, and written like you’re messaging a friend. Skip the heavy branding, logos, and corporate templates. Authenticity builds trust ✓
The Reply-To Strategy That Changes Everything 💬
Here’s a simple tactic that dramatically improves engagement: invite replies instead of always pushing action buttons.
Instead of “BOOK NOW” as your only call-to-action, try: “Thinking about visiting for [local event]? Reply to this email and let us know—we’d love to help you secure dates.”
This approach works particularly well for older demographics who are less comfortable navigating booking sites independently. They want human connection, and giving them permission to reply reduces friction and builds a relationship.
You’ll be surprised how many conversations start this way, leading to bookings you wouldn’t have captured otherwise 🎯
Social Media’s Real Role (It’s Not What You Think) 📱
Many vacation rental operators waste countless hours trying to build social media followings, hoping it will drive bookings. The reality? Social media for vacation rentals works best as social proof, not discovery.
Your Instagram or Facebook presence serves one primary purpose: validation. When potential guests see your social icon on your direct booking site and click through to find active, authentic content, it builds trust. They see you’re legitimate, engaged, and professional.
The winning strategy? One quality post per week, scheduled in advance. Batch-create content quarterly—spend a few hours creating and scheduling 12-15 posts, then forget about it for three months. Cross-post to both Instagram and Facebook to maximize efficiency.
Focus on behind-the-scenes content, guest experiences (with permission), local highlights, and property updates. Don’t stress about followers, engagement rates, or viral content. You’re building credibility, not becoming an influencer 👍
SMS Marketing: Powerful But Proceed With Caution ⚠️
Text messages have 98% open rates compared to email’s sub-50% rates. That’s compelling. But SMS marketing for vacation rentals requires extreme caution.
Unlike email, SMS has strict legal requirements. Recipients must explicitly opt-in to receive promotional messages—not just operational ones. The penalties for non-compliance can be severe, including lawsuits for tens of thousands of dollars ⚖️
If you pursue SMS marketing, work with platforms that properly collect opt-ins with clear paper trails. Never text promotional content to phone numbers collected only for booking purposes. The risk isn’t worth the reward unless you’re operating with proper legal safeguards.
The Mindset Shift That Makes This Work 🧠
The biggest barrier to implementing repeat bookings email marketing isn’t technical—it’s mental.
Perfectionism kills progress. You don’t need flawless copy, sophisticated automation, or enterprise-level tools. You need to start somewhere. Build a simple three-email sequence. Test it. Refine it. Add more over time.
Many operators freeze because they want to do everything right from day one. They research tools for weeks, agonize over which platform to choose, and debate whether to hire help. Meanwhile, they’re collecting zero emails and sending zero campaigns 🙅
The mantra? Start somewhere. Pick a tool, write three emails, schedule them, and launch. You can always optimize later, but you can’t optimize what doesn’t exist.
Also, recognize your strengths. If writing isn’t your zone of genius, outsource content creation. If you love strategy but hate execution, hire help for implementation. Successful vacation rental marketing happens when you focus on what you do best and delegate the rest.
Your 30-Day Implementation Plan 📋
Ready to build your repeat bookings email marketing system? Here’s your roadmap:
Week 1: Set up email collection (implement Stay Fi or similar tool)
Week 2: Choose your email platform (options include Klaviyo, Mailchimp, or specialized vacation rental CRMs)
Week 3: Write your first three sequence emails—checkout thank you, direct booking offer, and 30-day check-in
Week 4: Load emails into your platform, test your automation, and go live ✅
That’s it. Nothing fancy. Just functional, effective, and ready to drive results.
As your list grows and you see bookings come through, add more emails to your sequence. Build your first campaign for an upcoming local event. Experiment with different subject lines and content approaches.
The beautiful part about repeat bookings email marketing? Every improvement you make benefits all future guests automatically. You’re building an asset that compounds over time 📈
Don’t Overlook the Money Already in Your Business 💵
Here’s the truth: your past guests represent the lowest-hanging fruit in your entire marketing strategy. They already know your property, trust your hospitality, and have positive associations with their stay (assuming you delivered a good experience).
Converting a past guest costs a fraction of acquiring a new one. They don’t need convincing that your area is worth visiting—they’ve already been. They don’t need to trust your photos are accurate—they’ve already stayed. They just need a reason to remember you exist and book again.
That’s what repeat bookings email marketing delivers. Not aggressive sales tactics, not desperate discounting, but gentle, valuable touchpoints that keep you present in their minds until they’re ready to book their next getaway 🏡
Ready to Transform Your Direct Booking Strategy? 🚀
Email marketing is just one piece of a comprehensive direct booking approach. Your website, SEO, guest experience, and follow-up systems all work together to reduce platform dependency and increase profitability.
If you’re ready to take control of your booking revenue and build a website that actually converts, CraftedStays provides vacation rental operators with fast, mobile-optimized, SEO-friendly websites that integrate seamlessly with your property management system. Set up your direct booking site in minutes and start capturing more revenue from every guest—including those valuable repeat bookings.
Start your free trial at CraftedStays.co →