How to Get Repeat Bookings for Vacation Rentals: 8 Proven Strategies
Turn one-time guests into loyal customers. Real tactics from a host who achieved a 12.7% rebooking rate in Year 1.
Here's the truth about vacation rental marketing: acquiring a new guest costs 5-7x more than getting a past guest to return. Yet most hosts focus all their energy on attracting new bookings through Airbnb and Booking.com, completely ignoring the gold mine sitting in their past guest list.
I'm Jason, and I run two vacation rentals in the Blue Mountains of NSW. In my first year, I had 100 guests stay. Here's what happened:
- • 94 guests gave me their email through my digital guidebook
- • I sent 3 automated rebooking campaigns (at 6, 9, and 12 months)
- • 24 guests rebooked directly (bypassing OTAs entirely)
- • That's a 12.7% rebooking rate and $9,600 in direct booking revenue
- • I paid $0 in OTA commissions on those 24 bookings
This guide shows you exactly how I did it—and how you can replicate these results with your properties. No gimmicks, just proven strategies with real numbers.
⚡ Quick Navigation:
- • Strategy 1: Capture Every Guest Email (90%+ Rate)
- • Strategy 2: Create an Unforgettable First Experience
- • Strategy 3: Send Strategic Follow-Up Emails
- • Strategy 4: Build Automated Rebooking Campaigns
- • Strategy 5: Create a Loyalty Program
- • Strategy 6: Track Guest Milestones & Personalize
- • Strategy 7: Leverage Social Proof & Reviews
- • Strategy 8: Encourage Referrals from Happy Guests
Capture Every Guest Email (90%+ Rate)
You can't market to guests you can't reach. The foundation of repeat bookings is owning the relationship—and that means having their email address.
The Problem Most Hosts Face:
- ✗Airbnb and Booking.com own the guest relationship
- ✗You can't legally email guests directly through OTA platforms
- ✗Asking for emails manually gets 20-30% success rate at best
- ✗After checkout, guests disappear and you have no way to reconnect
The 90%+ Email Capture Strategy:
- 1.Create a valuable digital guidebook: Include WiFi password, check-in instructions, local recommendations, house rules, emergency contacts
- 2.Send the link 3-5 days before check-in: Timing is key—guests are excited and eager for information
- 3.Require email to access: Gate the guidebook behind a simple email form. The value exchange is clear and fair.
- 4.Include marketing opt-in: Add a checkbox: "Keep me updated about future stays and special offers"
My Results:
- • Before: Manually asking for emails via message = 23% capture rate
- • After: Digital guidebook with email gate = 94% capture rate
- • Guests captured: 94 out of 100 first-year guests
- • Marketing opt-in rate: 87% (guests WANT to hear from you if you deliver value)
Action Step: Set up a digital guidebook this week. Tools like GuestLoop make this turnkey with built-in email capture and CRM integration. Or use a simple landing page builder + email marketing tool combo. Read more: How to Reduce Airbnb Fees Through Email Capture.
Create an Unforgettable First Experience
Before we talk about marketing for repeat bookings, we need to talk about earning repeat bookings. Guests don't return to mediocre experiences, no matter how good your emails are.
The 5 Pillars of Rebooking-Worthy Stays:
This is non-negotiable. "Clean" is the #1 factor guests mention when deciding to return. Hire professional cleaners, use checklists, and inspect yourself regularly.
Photos, description, amenities—everything must be 100% accurate. Guests forgive imperfections, but they don't forgive dishonesty. Underpromise, overdeliver.
Small gestures create big impressions: welcome note, local snacks, coffee/tea, guidebook with personalized recommendations. Cost: $10-15 per stay. Value: priceless.
Message before arrival, check in on Day 1, be available during stay (but not intrusive). Guests remember hosts who made them feel cared for.
Things break. WiFi goes down. Neighbors are noisy. How you handle problems matters more than avoiding them. Respond fast, fix immediately, follow up to ensure satisfaction.
💡 The Repeat Booking Question:
After every checkout, ask yourself: "Would I want to stay here again?" If the answer isn't an enthusiastic yes, fix what's wrong before marketing for rebookings.
Action Step: Review your last 10 guest reviews. What patterns emerge? If cleanliness, communication, or amenities are mentioned negatively, address those issues before sending rebooking emails.
Send Strategic Follow-Up Emails
Most hosts end communication at checkout. Smart hosts plant seeds for the next stay immediately.
The Post-Stay Email Sequence:
Subject: "Thanks for staying at [Property Name]!"
Thank you for choosing [Property Name] for your stay! We hope you had a wonderful time in [Location].
If you have a moment, we'd be grateful if you could leave a review of your experience. Your feedback helps us improve and helps future guests make their decision.
We'd love to host you again in the future. We often have special offers for returning guests—just reply to this email anytime you're planning your next trip!
Safe travels,
[Your Name]
Subject: "Did you try [Local Attraction]?"
This is a relationship-building email, not a sales pitch. Share a local secret they might have missed, ask if they tried your recommended restaurant, or tell them about an event happening soon. Keep it conversational and genuine.
⚡ Pro Tip: The Review Request Sweet Spot
Ask for reviews within 24-48 hours of checkout. Response rates drop 50% after 3 days. Make it easy: include direct links to Airbnb, Booking.com, Google, or your direct booking site.
Action Step: Create 2 email templates (thank you + follow-up) and save them in your CRM or email tool. Personalize the first name, property name, and one specific detail from their stay (shows you care).
Build Automated Rebooking Campaigns
This is where the magic happens. Most guests don't spontaneously remember to rebook—you need to be in their inbox at the right time with the right message.
The 6-9-12 Month Rebooking Formula:
Subject: "Miss [Location]? Here's 10% off your next stay"
Why This Works: Guests are starting to think about their next vacation but haven't booked yet. Perfect timing to plant the seed.
Expected Conversion: 2-3%
Subject: "Your favorite [Property Name] is available for [Season]"
Why This Works: Creates urgency with seasonal messaging. Reminds them of the specific property they loved.
Expected Conversion: 3-4%
Subject: "It's been a year! Time to come back?"
Why This Works: Anniversary effect—many guests vacation on similar schedules year-to-year. This taps into that pattern.
Expected Conversion: 5-7%
My Combined Results (Year 1):
- • 94 guests in my email list
- • Sent 3 campaigns (6, 9, 12 months)
- • 24 rebookings (12.7% total rebooking rate)
- • $9,600 in direct booking revenue
- • $0 paid to OTAs on these bookings
Action Step: Set up automated email campaigns at 6, 9, and 12 months. Use a vacation rental CRM with built-in automation, or use an email marketing tool like Mailchimp/ConvertKit with date-triggered workflows.
Create a Loyalty Program for Repeat Guests
Repeat guests deserve to feel special. A formal loyalty program gives them tangible reasons to choose you over competitors.
What to Offer Repeat Guests:
- 10-15% Direct Booking Discount: You're still making more than paying OTA fees (15-20%), and guests save money. Win-win.
- Welcome Back Gift: Bottle of local wine, artisan chocolates, handwritten note. Cost: $15-20. Impression: priceless.
- Priority Booking: Give them first access to peak season dates before listing publicly. Makes them feel VIP.
- Flexible Check-In/Out: When schedule allows, offer early check-in or late checkout. Costs you nothing, delights them.
- Free Night After X Stays: "Book 3 times, get your 4th night free." Creates a goal and incentive to return.
⚠️ Important: Check your OTA agreements for price parity clauses. Solutions:
- • Frame discounts as "repeat guest appreciation" (not publicly advertised)
- • Use promo codes sent via email (not shown on website)
- • Offer perks instead of discounts (free breakfast, upgrade, late checkout)
Action Step: Create a "VIP Repeat Guest Program" document outlining benefits. Email it to guests after their 2nd stay with the subject: "Welcome to our VIP Guest Program!"
Track Guest Milestones & Personalize Outreach
Generic emails get ignored. Personal emails get opened, read, and acted upon.
Milestones to Track:
"It's been one year since you first stayed with us! We'd love to have you back..."
"Happy birthday! Celebrate with 20% off your next stay..."
If they celebrated an anniversary or honeymoon, remember it: "Planning your 2nd anniversary?"
Celebrate their 3rd, 5th, or 10th stay with a special gift or recognition.
💡 The Power of Memory:
Keep notes in your CRM about each guest: Did they bring kids? A dog? Celebrate something special? Mention a local restaurant they loved? Reference these details in future emails—it shows you remember them as individuals, not just booking numbers.
Action Step: Add custom fields to your CRM or spreadsheet: "Special Occasions," "Memorable Details," "Favorite Local Spots." Fill these in within 24 hours of checkout while memories are fresh.
Leverage Social Proof & Past Guest Reviews
When reaching out to past guests, remind them why they loved staying with you by showcasing what other guests are saying.
How to Use Social Proof:
- →Include Recent 5-Star Reviews: In rebooking emails, add a quote from a recent guest: "Best vacation rental we've ever stayed in!"
- →Highlight Awards/Recognition: Superhost status, Booking.com awards, Guest Favorite badges—mention these achievements.
- →Show Improvements: "Since your last stay, we've added [new amenity/upgrade]." Shows you're constantly improving.
- →Create FOMO: "We've been fully booked the past 3 weekends—don't miss out on [upcoming season]!"
Action Step: Create a "Social Proof Bank"—a document with your best reviews, awards, and guest testimonials. Pull from this when writing rebooking emails to add credibility.
Encourage Referrals from Happy Repeat Guests
Repeat guests are your best marketing channel. They've stayed multiple times—they're basically brand ambassadors. Make it easy for them to refer friends.
The Referral Program Formula:
- 1.Give them a unique referral code or link: Easy to share, trackable for you.
- 2.Reward both sides: Friend gets 10% off, referrer gets $50 credit or free night after 3 referrals.
- 3.Make it effortless: Pre-written message they can copy/paste or share via email, text, or social media.
- 4.Follow up and thank them: When a referral books, thank the referrer immediately and issue their reward.
⚡ When to Ask for Referrals:
- • After their 2nd or 3rd stay (proven loyalty)
- • After they leave a glowing 5-star review
- • In the post-stay thank you email: "Know anyone planning a trip to [Location]?"
Action Step: Create referral links or unique codes for your top 10 repeat guests. Email them: "We'd love to share [Property Name] with your friends—here's a special link for 10% off!"
Implementation Timeline (Realistic)
Set up digital guidebook with email capture, create post-stay thank you email template
Build 6-9-12 month automated campaigns, document loyalty program benefits
Start collecting emails from new guests, send first follow-up sequences
First 6-month rebooking emails go out, track results and optimize
Expect 10-15% of past guests to rebook, with 20-30% of those becoming regulars (3+ stays)
How to Measure Rebooking Success
Key Metrics to Track:
- • Rebooking Rate: (Repeat bookings ÷ Total guests) × 100
- • Email Capture Rate: (Emails collected ÷ Total guests) × 100
- • Campaign Open Rate: Target 20-30% for hospitality
- • Campaign Click Rate: Target 3-5%
- • Revenue from Repeat Guests: Track separately
Benchmark Goals:
- • Good: 8-10% rebooking rate
- • Great: 12-15% rebooking rate
- • Exceptional: 20%+ rebooking rate
- • Email Capture: 90%+ is achievable
- • Referral Rate: 5-10% of repeat guests
Pro Tip: Use a vacation rental CRM that automatically tracks these metrics. Manual tracking in spreadsheets works but requires discipline.
Common Mistakes That Kill Repeat Bookings
❌ Emailing Too Often
Sending weekly promotional emails will get you unsubscribed. Stick to strategic timing: 6, 9, 12 months + occasional seasonal offers.
❌ Generic "Come Back" Messages
"We'd love to have you back!" is boring. Personalize: "Ready for another [hiking/beach/wine tasting] adventure?"
❌ Not Segmenting Your List
Families with kids need different messaging than couples on romantic getaways. Segment by guest type for better results.
❌ Forgetting to Follow Up
If a past guest inquires but doesn't book, follow up! "Still interested in [dates]? I'm holding them for you until tomorrow."
❌ Ignoring Negative Experiences
If a guest had issues during their stay, address them BEFORE marketing for rebookings. An apology + resolution can turn critics into advocates.
Tools That Make Repeat Bookings Easier
All-in-One Solution:
GuestLoop combines digital guidebook, email capture (90%+ rate), CRM, and pre-built rebooking campaigns.
Plans from $49-199/month • 14-day free trial
Separate Tools Approach:
- • Digital Guidebook: TouchStay ($30/mo), Hostfully ($59/mo)
- • Email Marketing: Mailchimp ($20-50/mo), ConvertKit ($29+/mo)
- • CRM: HubSpot (free tier), Airtable ($10+/mo)
Total: $60-140/month across multiple tools
Ready to Build Your Repeat Booking Engine?
Start capturing guest emails and automating rebooking campaigns today. The sooner you start, the sooner you'll see your first repeat bookings.
14-day free trial • 90%+ email capture rate • Pre-built campaigns