AUTOMATED MESSAGING for short-term rentaLs & BOUTIQUE hotels

Automated messaging at each step of the stay

Start now
Start now
See pricing
See pricing

Share essential details with guests automatically

✔ OTAs ✔ Airbnb ✔ Vrbo ✔ Booking.com ✔ Expedia ✔ Direct Bookings

✔ Property Info ✔ Recommendations & Upsells ✔ Hospitality & Branding ✔ FAQs & Answers
★★★★★

"We switched to Happy Guest because it's much more all-encompassing than just a guide book. We can add contracts for guests to sign — for example."

Rental Host / Operator
Rental Host / Operator
80%
Fewer guest questions
70%
Average time saved per week
+67%
More listings in year one
★★★★★

"Thank you for the assistance — it has been a smooth weekend with check ins!"

Rental Host / Operator
Rental Host / Operator
★★★★★

"We love using Happy Guest in our hosting business! It streamlines our check-in process and enhances the guest experience!"

Rental Host / Operator
Rental Host / Operator

Configure automated messages once per property

Messages go out to wherever guests booked — Airbnb, Vrbo, Booking.com, or any connected channel:

Activated by reservation milestones and guest activity, regardless of time zone or when you last logged in.

 
✦
Booking Confirmed
Instant · Automatic · No action needed
The moment a booking comes in, your welcome link goes out automatically. The guest is immediately walked through the compliance steps — no action needed on your end.
✦
Registration Completed
Agreements · ID · Damage protection
Once the guest completes registration, they receive everything they need before arrival — local tips, property details, and anything worth knowing ahead of time.
✦
Check-In Ready
Access details · Right timing · No confusion
Access instructions go out at the right moment before arrival. Guests show up knowing exactly what to do, without having to ask.
✦
During the Stay
Mid-stay · Recommendations · Upsells
A mid-stay message keeps the experience feeling looked after — a friendly check-in, a local recommendation, or a well-timed offer, depending on how you've set it up.
✦
Checkout Approaching
Departure reminder · Smooth handoff
A departure reminder goes out before they leave, so checkout runs smoothly and your follow-up is already in motion before they've left the property.
✦
After They Leave
Thank-you · Review request · Book direct
A thank-you, a review request, and an invitation to book directly with you next time — all sent automatically, in your voice, at the right moment.

Make every message sound personal

Every property has its own feel — maybe excited, serene, or somewhere in between. Choose and adapt any automated message template to give each stay a personal touch.

 

Keep your inbox quiet

Questions happen when details get missed or delayed — which is how late-night messages and inbox fatigue begin. By running routine communication automatically, reactive outreach and inbound messages decrease naturally.

  • Essential information is released sequentially

  • Access and instructions are delivered on time

  • Questions about parking or the espresso machine are already answered

  • Checkouts happen on time and as planned

  • You only step in when it’s truly needed

★★★★★

"Easy to use and seamless upsell to guests! Happy with all the speedy customer service support."

Yolanda Yu · Rental Host
Rental Host / Operator
★★★★★

"I won't do a reservation without Happy Guest. The New Yorker in me knows better haha."

Leigh · Rental Host
Rental Host / Operator
★★★★★

"Happy Guest has been amazing for our business. I would recommend them to every PM I could."

Rental Host / Operator
Rental Host / Operator
+30%
Increase in top-line revenue
90%
Of hosts are not fully STR compliant
85%
Of STRs are managed by independents
50
States now regulate short-term rentals

Frequently asked questions about automated messaging

  • Not at all! You control tone and content — automation controls the timing and sequence. Guests receive messages that sound like they were written specifically for their stay — because you wrote them.

  • Yes. Templates are configurable by listing, property type, or stay duration. Each property can have its own messaging sequence.

  • Through the booking channel your guest used — Airbnb, Vrbo, Booking.com, and others — and via email when supported. No app download required for guests.

  • No. Your PMS handles reservations and basic messaging. Happy Guest handles the structured guest journey after booking — ensuring the right messages, requirements, and offers are delivered in sequence. It does not replace inventory or billing systems like Guesty, Hostaway, or OwnerRez.

  • You can step in at any time. Automation handles routine sequencing — not operator judgment.

  • When a reservation is created, milestone-based messages are triggered automatically — tied to booking confirmation, registration completion, arrival timing, and departure. The right information reaches your guest at the right moment, reducing repetitive questions before they start.

  • A guest communication platform automates the messages your guests receive throughout their stay — from booking confirmation through checkout. Instead of sending messages manually, the right information is triggered automatically at each stage of the reservation. Happy Guest manages this entire sequence and delivers messages through the channels your guests already use — no app download required.

  • Most guest questions are about timing — "when do I get the door code?", "what time is check-out?", "where's the WiFi password?" When this information is delivered automatically at exactly the right moment, guests don't need to ask. Operators running automated messaging consistently report a significant reduction in routine inbound messages.

  • Yes. This is one of the core reasons operators adopt it. As your portfolio grows, manual communication becomes impossible to maintain at a consistent quality level. Automation ensures every guest receives the same structured, professional communication — regardless of how many properties you manage or what time they book.

  • Duve and Operto offer digital check-in and messaging as part of broader hotel-focused platforms. Happy Guest focuses on the full guest operations layer — compliance, messaging, and revenue — in a workflow built specifically around the check-in link and gated access model. It works alongside tools like these when needed, and directly replaces manual workflows when not.

Happy Guest provides automated guest messaging tools as part of the guest journey workflow. Message delivery depends on integration with connected booking channels and PMS platforms. Hosts remain responsible for message content, timing appropriateness, and compliance with applicable platform communication policies.
Best for STR automations

Get a demo and see it yourself

Book a 1-on-1, 45 minute demo with your property pulled up on screen. We'll show you exactly how check-in, agreements, and damage protection run themselves — and answer anything you want.

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