Best AI guest messaging tools, 2026
AI guest messaging tools, by who they fit.
Six options for short-term rental managers who want AI to answer guests, listed A to Z with who each one fits best. We make GuestReply AI, so we've kept to what each vendor publishes and linked it.
At a glance
Six options, at a glance
Last checked: November 3, 2026. Not a ranking: the tools are listed A to Z. Vendor facts are their own claims, linked below, not tested by us.
Spotted something out of date? Write to support@guestreply.ai and we'll fix it.
| Tool | Published price | Free trial |
|---|---|---|
| AI built into your PMS | Not compared here | Check with your PMS |
| Besty | A share of revenue, quoted on a call | None mentioned, demo instead |
| Conduit | Messaging from $18 per unit a month | None mentioned, demo instead |
| Enso Connect | Core from $16 per unit a month, billed yearly | None mentioned, demo instead |
| GuestReply AI | $8 per listing a month for listings 1–50 | 30 days, 60 for Smily, Hostaway and Guesty |
| HostBuddy AI | From $7 per property a month | 14 days, no credit card |
Best for teams who want AI from their PMS vendor
AI built into your PMS
Some PMSs have their own AI for guest replies. Guesty's ReplyAI and AI Autopilot draft or auto-send replies (Guesty). Hostaway's AI Replies draft and send guest messages, and you choose which ones are reviewed first (Hostaway). Hospitable's Inbox AI drafts replies and sends them on its own only if you turn on Auto Reply (Hospitable).
Check what your PMS plan includes. We don't compare their prices here. GuestReply AI connects to all three if you'd rather use a separate tool.
Best for operators who'd rather hand over the digital side
Besty
Besty now describes itself as AI-native vacation rental management: an AI system plus an operations team that runs guest messaging, revenue, owner reporting, cleaning coordination, phones and marketing. You can also take the software suite on its own. Sources: Besty homepage, capabilities.
It asks for at least $500K in annual guest revenue and a 4.7 or better rating on Airbnb or a similar OTA. Pricing is one share of revenue, quoted on a sales call, with no annual lock-in. So there's no per-listing price to set against a messaging tool. Source: Besty homepage.
Best for operators who want voice agents and operations tools
Conduit
AI agents for hospitality: chat and voice agents for guests, and internal agents for operations. It lists 19 PMSs and answers on booking-platform messaging, email, SMS, WhatsApp, phone calls, website chat and Instagram DMs. Sources: integrations, short-term rentals.
Messaging starts from $18 per unit per month, and Startup is $899 per month flat for 0 to 25 units. No free trial is mentioned. It offers a demo. Source: pricing.
GuestReply AI vs Conduit →Best for hotels and rentals that want a guest portal
Enso Connect
An AI guest experience platform for hotels and vacation rentals. Besides AI messaging in a unified inbox, its Boarding Pass portal handles ID verification, check-in, smart lock codes and upsells. Source: Enso Connect homepage.
Core starts from $16 per unit per month billed yearly, with a 5-unit minimum. It starts with a demo, and its homepage offers an ROI guarantee. Sources: pricing, homepage.
GuestReply AI vs Enso Connect →Best for property managers who want to start self-serve
GuestReply AI
AI guest messaging for short-term rental property managers, through their PMS: Guesty, Hospitable, Host Tools, Hostaway, Hostify, Lodgify, OwnerRez or Smily. Replies go out on their own or wait as drafts, in the guest's own language by default. What it can't answer goes to your team with a note listing the issues.
$8 per listing a month for listings 1–50, $6 for 51–200 and $4 from listing 201, with a $40 minimum monthly charge. 30 days free, or 60 for Smily, Hostaway and Guesty, with no demo or sales call. That's us, so weigh this entry accordingly.
GuestReply AI pricing →Best for hosts who want a low per-property price
HostBuddy AI
AI guest messaging connected to your PMS, from a team that says it was created by hosts, for hosts. Its FAQ names 14 PMSs, including Smoobu, Hostex, Beds24 and Tokeet. Sources: HostBuddy AI homepage, FAQ.
Plans run from $7 to $12 per property, monthly, and the 14-day free trial needs no credit card. Sources: pricing, AI messaging.
GuestReply AI vs HostBuddy AI →Try GuestReply AI free.
30 days free with every feature, and nothing is charged during the trial. You sign up yourself, and first-time customers get a 30-day money-back guarantee on their first paid month.