How to automate STR guest messages with Claude
According to the Guest Experience skill, most management offices spend 35–50% of their time answering the same 30 guest questions. The skill turns those into a scheduled pre-arrival sequence and a per-property answer set, and keeps a human on anything negative.
Step by step
Load the Guest Experience skill
In Claude.ai, create a Project, paste the Guest Experience SKILL.md into the Project instructions and save. Or run
npx github:msg2ai/vacationrental-team-skills installonce and Claude Code picks the right skill from your prompt.Map the pre-arrival sequence
T-7: a welcome email confirming dates, linking the welcome book and offering optional upsells. T-3: the SMS / WhatsApp concierge opt-in. T-1: check-in instructions, door code, Wi-Fi and parking. T-0: the arrival-day welcome SMS with the 24/7 line.
Personalize by guest and market
Ask Claude to vary the sequence by group composition (family with kids, couples, large group, business stay) and by market (beach, mountain, urban).
Build each property's answer set
Cover the top 30 questions per property: Wi-Fi, parking, trash and recycling, HVAC, TV, pool / hot tub, grill, pets, quiet hours, check-in and check-out policy, local restaurants and urgent care, and the emergency contact. This is the config the AI Ambassador SMS / WhatsApp concierge answers from.
Set the escalation rules
Any unanswered or sentiment-negative question routes to the on-call human in under 60 seconds. In-stay issues get a “we hear you, we're on it” reply within 5 minutes and are routed to Housekeeping & Maintenance with a severity tag.
Close the loop after checkout
Departure day: a thank-you SMS with the review link. T+1 and T+3: gentle follow-ups if there's no review yet. T+5: a one-tap NPS survey. 1–3 star guests get routed to a human for a make-it-right call first.
The prompt to paste
What you get back
- A per-property pre-arrival sequence, saved to 08-guests/sequences/pre-arrival/
- A per-property concierge config covering the top 30 guest questions
- Review-request and NPS follow-ups timed to departure
Tips from the skill
- Pre-arrival communication is where loyalty is built. Don't skip it.
- Property quirks (the weird thermostat, the cabinet that sticks) belong in the concierge config — not in the cleaner's head.
- Negative feedback always gets a human first.
- Upsells should feel like service, not a sales pitch.
- Live SMS / WhatsApp automation runs on AI Ambassador for Vacation Rentals, a separate paid product. The skill itself is free.