For Real Estate Investors ·
What you'll accomplish
The check-in code question, the Wi-Fi password question, the "what time is checkout" question: they all sound the same after the fiftieth time you've typed the answer. Hospitable connects to your listing calendar and inbox across platforms and lets AI-suggested or fully automatic replies handle the routine questions, while flagging anything unusual for you to answer directly. After this setup, you'll have your listings connected, a set of message templates ready, and AI replies running on at least one property.
What you'll need
Go to hospitable.com and sign up. The first real step is connecting your listing platforms so Hospitable's live calendar sync can keep your listings, cleaners, and reviews aligned across Airbnb, Vrbo, Booking.com, and your direct booking site, all from one place.
What you should see: Your listings appearing inside Hospitable's dashboard with a synced calendar for each. Troubleshooting: If a listing doesn't sync, double check you're authorizing the account that actually owns that listing, especially if you manage properties under more than one platform login.
Hospitable comes with pre-built message templates covering common stages of a guest's stay (booking confirmation, pre-arrival instructions, checkout reminders), and you can customize them or build your own. Shortcodes let a template pull in details like the check-in time automatically, without you typing them fresh for every guest.
What you should see: A library of message templates, each tied to a stage of the guest journey, ready to send automatically or on demand. Troubleshooting: If a shortcode doesn't populate correctly in a preview, check that the underlying field (check-in time, for instance) is actually set correctly for that listing.
Messaging rules let you schedule a template to go out automatically at a specific point relative to a booking, like two days before arrival or the morning of checkout, instead of you remembering to send it.
What you should see: A list of active messaging rules, each showing which template it sends and when. Troubleshooting: Overlapping rules (two templates scheduled for the same moment) can send duplicate or conflicting messages. Review your rule list for overlaps after setting up more than one.
Hospitable's messaging system can detect guest questions across a wide range of common topics and answer them using your pre-written responses almost instantly. You can start with AI-suggested drafts you review before sending, then move to fully automatic replies once you trust the pattern.
What you should see: Guest messages arriving in your Unified Inbox with a suggested AI reply attached, or in full automation mode, already answered with a note showing it was AI-handled. Troubleshooting: If the AI's suggested tone doesn't sound like you, revisit your message templates and Knowledge Hub content (Step 5), since the AI draws its answers from what you've given it.
For questions that don't fit a scheduled template (restaurant recommendations, transit directions, an unusual house rule), Hospitable's Knowledge Hub lets you upload information the AI can draw on to generate a suggested draft, which you then review and edit before sending using the Suggest with AI button in the inbox.
What you should see: A generated draft reply appearing in the message composer, based on the Knowledge Hub content and the guest's actual question. Troubleshooting: If the draft misses the point of the question, the Knowledge Hub likely needs more detail on that topic. Add it once, and future similar questions should generate better drafts.
Hospitable's own AI runs inside the platform using your Knowledge Hub and templates, so it already has the property context it needs. If you want to draft something outside the platform, like a template you'll then paste into Hospitable, keep guest names and booking IDs out of the prompt entirely. Describe the situation generically.
Drafting a new template for an unusual situation: "Write a short, friendly message template for a short-term rental guest explaining a temporary situation, [general description, e.g. a construction noise nearby during their stay], including a brief apology and what we're doing about it. Keep it under 100 words and leave a placeholder for arrival date."
Drafting a house manual section: "Help me write a clear house manual section for [general topic, e.g. trash and recycling pickup days] for a short-term rental, in a friendly but concise tone guests will actually read."
Turning a recurring question into Knowledge Hub content: "I keep getting asked some version of [general question type, e.g. the best way to get downtown without a car]. Help me write a thorough, useful answer I can add to my property's guest information so future questions like this get answered well automatically."
Use GPT-5.6 Sol or Sonnet 5 for any of these, then paste the result into Hospitable's template or Knowledge Hub editor. Never include a guest's actual name, a booking ID, or any detail specific to one reservation in a prompt written outside the platform.