Vacation rental businesses obsess over acquiring new guests. But the most profitable bookings come from people who've already stayed with you.
The problem? Most property managers send one confirmation email and never contact guests again. They're leaving money on the table.
Here are the 7 email automations every vacation rental business should have running — and the exact timing and content that works.
Flow #1: Booking Confirmation Sequence
This isn't just a receipt. It's the start of the guest relationship.
Email 1: Immediate confirmation
- Booking details and payment confirmation
- What happens next
- Direct contact information
Email 2: 24 hours later
- Welcome message from the property manager
- Link to destination guide or local tips
- Upsell opportunities (early check-in, add-ons)
This sequence builds anticipation and opens the door for upsells.
Flow #2: Pre-Arrival Sequence
Start 7 days before check-in. Reduce anxiety and prevent cancellations.
Email 1: 7 days before
- Countdown to their stay
- Weather forecast for their dates
- Packing suggestions
Email 2: 3 days before
- Check-in instructions
- Property access details
- Contact for questions
Email 3: Day before
- Final reminder with key details
- Mobile-friendly check-in guide
- "We're excited to host you"
Flow #3: Mid-Stay Check-In
For stays of 5+ nights, send a mid-stay email. Timing: halfway through their stay.
What to include:
- "How's your stay going?"
- Quick feedback request
- Offer to help with anything
- Local recommendations
This catches problems before they become negative reviews.
Flow #4: Post-Stay Review Request
Reviews drive future bookings. Automate the ask.
Email 1: Day after checkout
- Thank you for staying
- Direct link to leave a review (make it one click)
- Simple, personal ask
Email 2: 4 days later (if no review)
- Gentle reminder
- Emphasize how reviews help
- Same one-click review link
Keep it simple. Long emails asking for reviews don't work.
Flow #5: Win-Back Campaign
Target past guests who haven't booked in 12+ months.
Email 1: "We miss you"
- Personalized subject line with their name
- Reminder of their past stay
- What's new at the property
Email 2: 7 days later
- Exclusive returning guest offer
- Limited-time discount
- Urgency element
Email 3: 14 days later
- Last chance messaging
- Offer expires
Past guests convert at 3-5× the rate of new prospects.
Flow #6: Anniversary/Birthday Emails
If you collect birthdays, use them. If not, use booking anniversaries.
Timing: 2-3 weeks before the date
Content:
- Personal celebration message
- Special offer for their occasion
- Invite to book their next getaway
These emails have the highest open rates of any automation we run.
Flow #7: Seasonal Campaigns
Not technically a flow, but essential for vacation rentals.
Key sends:
- Early booking incentives (announce next season's availability)
- Last-minute deals (fill gaps in the calendar)
- Holiday specials (Thanksgiving, New Year's, Spring Break)
- Shoulder season promotions (drive off-peak bookings)
Segment these by past booking behavior. Show guests properties similar to what they've booked before.
Technical Setup Essentials
Before launching these flows, ensure you have:
- Clean email list with proper consent
- Integration between your PMS and email platform
- Proper unsubscribe handling
- Mobile-responsive templates
- Deliverability monitoring
Metrics to Track
For each flow, monitor:
- Open rate — Aim for 30%+ (vacation rental emails typically perform well)
- Click rate — 5%+ is strong
- Revenue attributed — Track bookings from email links
- Unsubscribe rate — Keep under 0.5%
Start Here
Don't build all 7 flows at once. Prioritize:
- Post-stay review request — Immediate ROI through more reviews
- Pre-arrival sequence — Reduces cancellations and support questions
- Win-back campaign — Drives repeat bookings
Once these are running, add the others incrementally.