How Guest Message Automation Works

When a guest sends a message through a channel connected to Hostaway (Airbnb, Booking.com, direct, etc.), the following happens:

1. Hostaway receives the message and fires a webhook event to Enhanced Rentals.
2. Enhanced Rentals looks up the reservation associated with the conversation and identifies the property.
3. The system finds all AI assistants configured for that property and evaluates each one's conditions against the current reservation status to select which assistant should respond.
4. The selected assistant processes the message and generates a reply after a configurable delay.
5. The reply is sent back to the guest via Hostaway.

Each AI assistant has a set of conditions that control when it is allowed to respond. When a message arrives, the platform checks every assistant assigned to the property and picks the first one whose conditions match the current reservation state.

The most common condition is reservation status. Examples of statuses you can use as a condition:

• inquiry — the guest has sent an enquiry but has not yet booked. Useful for a sales-oriented assistant that answers availability and pricing questions.
• new — a booking was just confirmed. Ideal for a welcome message or check-in instructions assistant.
• modified — the reservation was changed (dates, guests, etc.). Useful for proactive messaging about the updated stay details.

You can create multiple assistants for the same property, each covering a different status — the platform evaluates them in order and uses the first match.

Each assistant has a configurable reply delay — the number of minutes the system waits before sending the response. The default is a few minutes, which avoids instant-response patterns that guests may find jarring.

The delay for inquiry messages may be longer than for confirmed reservation messages, since a faster response to an in-stay issue is generally expected.

Automation stops for a conversation when:

• A team member replies to the guest manually (the bot detects the human response and stands down).
• The guest triggers an escalation keyword or the assistant determines the request is beyond its capability.
• The assistant is disabled for the property.

Once a human takes over a conversation, the bot will not reply again unless explicitly re-enabled for that thread.

The AI assistant handles text-based guest messages. It cannot:

• Modify reservations or process refunds.
• Access third-party systems outside of Hostaway.
• Send proactive messages (it only replies to incoming messages).
• Respond to messages sent in Hostaway's internal notes or between team members.