Smily Inbox — Vrbo Messaging Guide

This guide explains how messaging between Vrbo and Smily works. It covers what you can do, what happens automatically, and what the system cannot do.

Overview

When a guest contacts you on Vrbo, their messages automatically appear in your Smily Inbox. You can reply from Smily and your reply goes back to Vrbo — appearing as written by you as the host, regardless of which team member sent it in Smily.

Think of Smily Inbox as a mirror of your Vrbo conversation, always kept in sync..

How Messages Flow

Guest writes to you on Vrbo

1. The conversation and all messages appear in your Smily Inbox in near real-time. In rare cases it can take up to 15 minutes.
2. When a new message arrives, Smily pulls the full conversation history from Vrbo — so you always see the complete thread, not just the latest message.
3. The conversation is automatically linked to the related booking, inquiry, or both — depending on what Vrbo has connected to the conversation.

You reply from Smily

1. You write a reply in Smily Inbox and send it.
2. It appears on Vrbo as a message written by you as the host — no matter which member of your team sent it in Smily.

Important: Conversations always start on Vrbo. You cannot open a brand-new conversation with a guest from Smily — the guest must send the first message on Vrbo.

What You See in Your Inbox

Guest messages

All text messages sent by the guest on Vrbo appear in Smily exactly as written.

Your own messages

Messages you sent on Vrbo before or after connecting Smily also appear in the conversation.

Automatic system notes

Some Vrbo events generate an informational note in your Smily Inbox automatically. These are for your reference only — the guest never sees them. They appear when:

• A new inquiry is received (includes check-in/out dates, number of guests, property name)
• A duplicate inquiry is detected
• A payment is overdue
• A booking is cancelled (by you or by the guest)
• The guest requests a cancellation
• A value-added service is purchased

These notes give you context right inside the conversation so you don't have to look it up elsewhere.

Internal notes

You can write internal notes in Smily that are visible only to your team. Internal notes are never sent to Vrbo or shown to the guest.

Booking Connection

When a conversation arrives, Smily automatically connects it to the related inquiry, reservation, or both, based on what Vrbo has linked to that conversation. This means you can see the booking details directly alongside the messages.

Attachments

Receiving attachments from guests

If a guest sends a file on Vrbo, it will appear as an attachment in Smily. Delivery is near-instant in most cases, but can take up to 30 minutes if Vrbo is slow to make the file available.

Supported file types depend on what Vrbo allows, images, PDFs, and common document formats are accepted.

Sending attachments from Smily

You can attach files to your replies in Smily. They will be sent to the guest on Vrbo.

What can go wrong with attachments

Occasionally an attachment may fail to sync entirely. When this happens, a note is automatically added to the conversation telling you how many attachments could not be delivered. In that case, send the file directly on Vrbo.

Timing

Limitations

You cannot start a conversation from Smily

The first message must always come from the guest on Vrbo. Smily does not support initiating a new Vrbo conversation.

Message edits and deletions are not synced

If a message is edited or deleted on Vrbo after it has already appeared in Smily, the change will not be reflected. The original version remains.

Internal notes stay in Smily only

Notes you mark as internal are never sent to Vrbo. If you accidentally write something in a regular reply that you meant to keep internal, it will be delivered to the guest on Vrbo.

Read receipts and typing indicators are not supported

Smily does not show whether a guest has read your message or is currently typing a reply.

Delivery is near real-time but not guaranteed instant

In rare cases, messages and replies may take up to 15 minutes to appear — and attachments up to 30 minutes. This can happen if Vrbo is slow to process or make content available. If something seems delayed, wait a few minutes before taking action.

Sync failures

If a message fails to sync after several automatic retries, a system note is added to the conversation explaining what happened. In that case, reply directly on Vrbo to make sure the guest receives your message.

Frequently Asked Questions

Can I reply on Vrbo directly instead of Smily?

Yes. If you reply on Vrbo, the message will appear in Smily near-instantly (up to 15 minutes in rare cases).

What happens if two team members reply at the same time — one on Smily and one on Vrbo?

Both replies will sync and both will appear in the conversation on both sides. Both messages are delivered.

Why does a conversation show a note I didn't write?

Certain Vrbo events (such as a new inquiry or a cancellation) automatically create an informational note in the conversation. These are generated by the system to give you context. The guest does not see them.

An attachment didn't come through — what do I do?

If a note in the conversation says some attachments failed, send the file directly on Vrbo as a fallback.

Will I see my old Vrbo conversations in Smily?

Past conversations are not pre-imported. However, when a new message arrives in an existing thread, Smily pulls the full history of that conversation — so you will always see the complete context as soon as there is new activity.