Last checked: 14 October 2026
Until recently, the AI built into a property management system could draft a reply and wait for someone to press send. That's no longer true on either of the two PMS platforms most professional operators use. Guesty and Hostaway both now let their AI answer guests on its own, within limits you set.
Some comparison pages still say neither platform offers full auto-reply. That was fair in early 2025. It isn't now. This guide compares only the AI layer, not the whole PMS, so you can see what each one actually does and where it stops.
What each one is
Guesty ReplyAI and ReplyAI Autopilot
ReplyAI started as a drafting tool. It soft-launched in February 2024 and went public in July 2024. It learns tone from your past messages, detects sentiment, writes conversation recaps and suggests replies for your team to approve.
On 22 April 2026 Guesty added ReplyAI Autopilot and AI Task Creation. Autopilot sends replies without a person approving them, and Task Creation turns message content into maintenance tasks. Guesty describes both as steps towards an "agentic AI layer" inside the PMS.
Hostaway AI Replies and AI Auto-Reply
Hostaway announced AI Auto-Reply on 5 August 2025 with early access, and general availability was expected in late October 2025. It sits alongside AI Replies, which drafts answers in the inbox.
In late June 2026 Hostaway also launched AI CoHost. It's worth being clear about what that is. AI CoHost is a chat assistant for the operator, covering portfolio analytics, pricing suggestions, listing edits and message drafts, all carried out after you approve them. It isn't a guest messaging autopilot.
How much control you get
This is where the two differ most.
Guesty gives you a set of dials. You choose a confidence threshold, below which the AI won't send. You switch it on by property, set active hours, and decide which message categories it can answer. Long or complex messages can be filtered out and sent to staff. Negative sentiment can be answered or escalated. You can add a reply delay so answers don't arrive suspiciously fast, and write custom rules for things like refunds or late checkout.
Hostaway starts more cautiously. Draft mode is the default, and you turn Auto-Reply on topic by topic "once you're satisfied with the drafts". Its help guidance sorts requests by risk. Early check-in and late checkout are treated as medium risk to review, and refunds and compensation as high risk to handle personally. You can run test replies and set send delays.
Both approaches are sensible. Guesty's suits teams that want to tune behaviour precisely. Hostaway's suits teams that want to move one topic at a time and watch what happens.
What the AI knows
Both draw on what's already in the PMS, which is the main advantage of built-in AI.
Guesty's ReplyAI uses your reservation and listing data and past conversations, and you can upload extra knowledge such as PDFs and guides. It translates automatically.
Hostaway's AI uses reservation data, listing data, conversation history and custom host instructions, plus a Knowledge Base and customisable reply rules.
In practice the quality of either depends on how well your listings are documented. If the parking instructions only live in someone's head, neither tool will find them.
Beyond the reply
Tasks. Guesty's AI Task Creation turns guest messages into maintenance tasks in the same system your team already uses. Hostaway has no equivalent dedicated feature that we could find documented. AI CoHost can take some actions, but only after you approve them, and it's aimed at the operator rather than guest requests.
Upsells. Guesty surfaces upsells through its Guest App. Hostaway supports upsell workflows. Neither runs the full loop of checking the calendar, offering an early check-in in the conversation and updating the booking on its own, as far as public documentation shows.
Coordination with third parties. Neither PMS AI messages your cleaner or handyman to ask whether something can be done and then reports back to the guest. That remains the territory of marketplace apps.
Pricing
Both are inexpensive by design, because they're there to keep you on the platform. The exact terms are vague, though.
- Guesty: ReplyAI is listed as "freemium" on all tiers, and the pricing page doesn't define the term. Autopilot pricing isn't published. A "Guesty Ultimate" bundle includes ReplyAI.
- Hostaway: AI Replies are included in the subscription at no extra cost "for a limited time". The PMS itself is priced on quote.
Ask both vendors in writing what you'll pay a year from now. "Free for a limited time" is a phrase worth pinning down.
What they claim, and what's known
| Guesty ReplyAI Autopilot | Hostaway AI Auto-Reply | |
|---|---|---|
| Autonomous sending since | 22 April 2026 | General availability around October 2025 |
| Default mode | Configurable threshold | Drafts, then opt-in by topic |
| Main controls | Confidence threshold, categories, property, active hours, sentiment, delay, custom rules | Topics, risk tiers, rules, Knowledge Base, test replies, delays |
| Task creation from messages | Yes (AI Task Creation) | Not documented as a dedicated feature |
| Upsells | Via the Guest App | Upsell workflows |
| Third-party coordination | No | No |
| Published price | "Freemium", Autopilot not published | Included "for a limited time" |
| Vendor-reported automation | "Up to 80%" of incoming messages | "Up to 90%" of guest communication |
| Methodology published | No | No |
Checked 14 October 2026 against vendor pages and press coverage. Automation figures are the vendors' own and can't be compared directly.
The automation claims deserve caution. Neither vendor says what counts as handled, whether the figure is an average or a best case, or what share of messages it's measured against. The closest thing to a measured number is from 2024, when Guesty said its high-usage accounts used ReplyAI for about half of incoming messages. That was before Autopilot existed, and it described drafting.
Guesty's Autopilot is also very new. At around six months old, there's no independent evidence on how it performs across a range of portfolios. Hostaway's has been live longer but has no independent review either. Our guide on how to measure an automation rate sets out a way to test both on your own conversations.
Known complaints
Neither AI layer has attracted much specific criticism yet, partly because they're so new. The broader complaints about each PMS are worth knowing, because the AI depends on the platform underneath it.
Guesty reviewers on Capterra mention opaque pricing as modules add up, sync errors with Booking.com and Vrbo, and inconsistent support. Hostaway reviewers mention a laggy messaging inbox, notification delays and inconsistent channel sync. A messaging delay matters more once an AI is meant to answer in seconds.
Who should pick which
You're unlikely to switch PMS for the AI alone. Moving a portfolio between Guesty and Hostaway is a large job, and the gap between their built-in AI is smaller than the gap between either one and a dedicated autopilot. But if you're choosing a PMS now, or the AI is the deciding factor:
- Guesty's approach suits operators who want granular controls and task creation inside the PMS, and who are comfortable relying on a feature launched in April 2026.
- Hostaway's approach suits operators who want to start in draft mode and widen the AI's remit one topic at a time, with a clear risk framework built in.
If you're already on one of them, switch the built-in AI on first. It costs little or nothing, and it'll show you quickly which questions it handles and which it can't.
When to add a marketplace autopilot
Both platforms have marketplaces full of AI apps, and there's a reason those apps still exist. Look at adding one when:
- the built-in AI answers questions well, but your team still briefs cleaners, checks turnovers and chases maintenance by hand
- you need early check-in and late checkout handled end to end, checked against the cleaning schedule, rather than escalated every time
- the AI escalates so often that someone still watches the inbox all day
- you want to reach your team on WhatsApp or another channel they already use
Our PMS guides for Guesty and Hostaway go into more detail, and the buyer's questions work for any vendor. For a wider view of the tools, see AI guest messaging software compared.
Sources
- Guesty ReplyAI Autopilot and AI Task Creation launch (22 April 2026): https://digital-release.wowktv.com/business/press-releases/cision/20260422LN39847/guesty-launches-replyai-autopilot-and-ai-task-creation-to-power-proactive-operations-inside-the-pms
- Guesty on the communication agent: https://www.guesty.com/blog/communication-agent-pms/
- Guesty pricing: https://guesty.com/pricing
- ReplyAI usage in 2024: https://www.travolution.com/news/travel-sectors/accommodation/guestys-replyai-tool-sees-clients-leverage-it-for-50-of-communication
- ReplyAI launch (July 2024): https://hoteltechnologynews.com/2024/07/guesty-launches-ai-messaging-tool-to-enable-short-term-rental-hosts-to-deliver-automated-guest-communications/
- Hostaway AI Auto-Reply launch: https://www.travolution.com/news/travel-sectors/accommodation/hostaway-launches-ai-auto-reply-tool-for-vacation-rental-managers/
- Hostaway AI features: https://www.hostaway.com/features/hostaway-ai.md
- Hostaway AI CoHost: https://www.hostaway.com/features/ai-cohost/
- Guesty reviews on Capterra: https://capterra.com/p/159377/Guesty/reviews/
- Hostaway on Capterra: https://www.capterra.com/p/152433/Hostaway/