Best AI guest messaging and autopilot software for short-term rentals, compared (2026)

Last checked: 14 October 2026.

The AI guest messaging market changed a lot in the last twelve months. Guesty and Hostaway both now ship their own autopilot. Hospitable, OwnerRez and iGMS have added one too. The independent vendors have responded by moving beyond the reply, into tasks, voice, upsells and changes written back to the PMS.

This guide maps where things stand for operators on Guesty and Hostaway. It's built from public documentation, pricing pages, press coverage and review sites. We haven't run these tools side by side, and where a figure comes from the vendor, we say so. If you want to test them yourself, our guide to measuring automation rate sets out a method that works on any of them.

The quick answer

• Under about 15 listings, simple properties: start with the AI in your PMS. Guesty ReplyAI and Hostaway Auto-Reply are included in the subscription, at least for now, and may be all you need.
• 15 to 200 listings, team stretched by repeat questions: compare your PMS's AI with a couple of add-ons on a two-week trial. Lower-cost tools like HostBuddy suit lighter needs. Tools that also coordinate tasks earn more at this size.
• 200+ listings, multiple teams: look for a system that handles the work after the reply (tasks, team coordination, PMS updates) and can show results across a sample of your listings in days, not months. Our enterprise rollout playbook sets out how to run that trial.
• Upsells are the priority: Enso Connect and Besty are the strongest on revenue features.
• US enterprise PMS (Track, Streamline, Escapia): neither Track nor Streamline had native AI messaging that we could find, so Akia, Enso Connect, Conduit and Besty are the main options.
• You have developers and want full control: you can build your own. It's more work than it looks.

Five kinds of tool

The labels overlap, so it helps to sort the market by what each tool actually does.

1. Built-in PMS AI. Guesty ReplyAI, Hostaway Auto-Reply, Hospitable Inbox AI, OwnerRez Rezzy. No extra vendor, no integration, usually cheap or included. Mostly focused on the reply.
2. Reply-focused add-ons. HostBuddy, ProhostAI and similar. Lower cost, wide PMS coverage, more set-up from you.
3. Autopilot and agent add-ons. Conduit, Aeve, Boom's agent layer, Besty. They aim to handle the request end to end, including the tasks and coordination around it.
4. Guest experience platforms. Enso Connect, Akia, Duve, Operto. AI messaging sits alongside guest apps, check-in, upsells and, in some cases, voice. Several are hotel-first.
5. Build your own. An LLM connected to your PMS's API. Maximum control, and all of the maintenance.

At a glance

"Yes" means the vendor documents the feature. It doesn't tell you how well it works. Prices are as listed or reported in October 2026 and change often.

Built into your PMS

Guesty ReplyAI and ReplyAI Autopilot

ReplyAI started in 2024 as a drafting tool that learnt tone from past replies. In April 2026 Guesty added Autopilot and AI Task Creation, so the AI can now send on its own and create maintenance tasks from what guests write. You control it with a confidence threshold, message categories, active hours, sentiment handling and custom rules.

Strengths: no extra vendor or integration, and a good set of guardrails. Tasks live in the same system as everything else. Drawbacks: Autopilot is six months old and there's little independent evidence on how it performs yet. Guesty claims "up to 80%" of messages, without a published method. Autopilot pricing isn't published. Guesty reviews more broadly mention rising module costs and inconsistent support. Best for: Guesty operators who want to start with what they already pay for. More in our Guesty guide.

Hostaway AI Auto-Reply

Announced in August 2025 and generally available from late 2025. Replies start as drafts, and you switch on automatic sending topic by topic once you're happy with them. Hostaway's own guidance rates early check-in and late checkout as medium risk and refunds as high risk, to be handled personally. AI CoHost, launched in June 2026, is a separate assistant for portfolio tasks rather than a guest autopilot.

Strengths: built in, included for now, and a careful, topic-by-topic rollout. Drawbacks: "for a limited time" pricing means the cost may change. Hostaway's "up to 90%" claim has no published method. Some reviewers describe the wider messaging inbox as laggy. Best for: Hostaway operators who want a low-risk start. More in our Hostaway guide.

Hospitable and OwnerRez

Both are PMSs in their own right, so they matter mainly if you're choosing a PMS. Hospitable's autopilot is limited to its top plan and deliberately won't answer availability, early check-in, date changes, refunds or pricing. It also publishes one of the few measurable figures in the market: about 60% of its AI drafts are sent unedited. OwnerRez's Rezzy costs $9 per property per month and can run on schedules, for example automatic overnight and drafts in office hours.

Autopilot and agent add-ons

Conduit (formerly HostAI)

The most complete agent on paper. Conduit handles messages across channels, answers phone calls with a voice agent, and writes changes back to the PMS, from rescheduling cleans to issuing door codes. It works with Guesty, Hostaway, Track, Streamline and others, and it's unusual in publishing its prices.

Strengths: breadth, voice, PMS write-back, transparent pricing. Drawbacks: heavier than a small team needs. Typical rollout is four to eight weeks, and credit-based pricing makes the monthly bill less predictable. Its figures (70 to 90%) come from its own case studies, and much of the comparison content online is written by Conduit itself. It's also broadening into hotels. Best for: mid to large operators, multi-brand groups, and anyone who wants voice. See also what changed when HostAI became Conduit.

Aeve

An autopilot for Guesty and Hostaway that learns from listings and past conversations rather than a rule builder. It coordinates with managers, cleaners and maintenance over WhatsApp or email, then confirms the outcome with the guest and updates the PMS. It hands refunds, complaints and judgement calls to the team.

It also plans staff days from your staff list, re-planning when someone calls in sick, and scores every stay on service and property.

Strengths: focused on handling the request end to end, including the coordination. Two platforms deep rather than many wide. Live quickly, and it will run on your own past conversations before you commit. Drawbacks: only Guesty and Hostaway. No voice, by choice. Pricing isn't published, and third parties report a 12-month contract. It targets 70 to 80% on autopilot, which is vendor-reported, like everyone else's figures. Best for: Guesty and Hostaway operators at around 50 listings and up, where coordination takes most of the team's time.

Boom

Boom can sit on top of an existing PMS (its BAM agent layer works with Guesty, Hostaway, Track and more) or replace the PMS altogether. It runs separate agents for messaging, sales, reviews, operations and owners. It raised $12.7 million in October 2025.

Strengths: broad scope, flexible ways to buy, free trial credits. Drawbacks: few independent reviews so far. Moving to Boom as your PMS is a large migration. Best for: operators who want one vendor across messaging, operations and owner relations.

Besty AI

Besty sends on its own when it's confident and drafts when it isn't. Its strongest feature is a conversational upsell engine for gap nights, early check-in, late checkout and extras. It works with more than 14 PMSs, including Track and Streamline, and raised a $3.75 million seed round in July 2026.

Strengths: upsells, wide integrations, enterprise ambitions. Drawbacks: pricing isn't public. Some Capterra reviewers describe replies as occasionally impersonal or wrong, and recommend checking them, and some mention flaky integrations. Best for: mid to large operators who want messaging and revenue in one tool.

HostBuddy

A messaging add-on with SOP-driven replies, upsells and issue flagging, connected to about 20 PMSs. It's one of the cheaper options.

Strengths: price, wide PMS coverage, praised support. Drawbacks: the vendor claims 95%+ for top hosts, but an independent review estimated 40 to 50%. Capterra reviewers mention wrong details in messages and replies after staff had already responded. Writing the SOPs takes time. Best for: small to mid-sized operators on a budget.

Guest experience platforms

Enso Connect combines AI messaging with a guest app, ID checks, smart locks and some of the strongest upsell features in the market. It serves over 60,000 listings. Its autopilot was labelled beta in its own help centre at the time of writing. Pricing is by quote, with third parties reporting a commission on upsells. A small number of Trustpilot reviews raise billing and notice-period complaints.

Akia is hotel-first and strong on voice: its phone agent can take a payment during the call. It's an official Track partner, so it's common in US enterprise vacation rentals. Reviews on G2 and Capterra are few, and include complaints about contract cancellation.

Duve and Operto have launched AI guest agents in 2025 and 2026, marketed mainly at hotels.

Building your own

With an LLM API and your PMS's webhooks you can build a working assistant in days. Getting it accurate across hundreds of properties, safe on refunds and promises, and cheap at tens of thousands of messages a month is a much longer project. We've written a full tutorial, including what data to pull and where it gets hard.

What the market looks like now

The PMSs have caught up on the basics. Answering routine questions on autopilot is now a built-in feature, often included in the subscription. Add-ons that only reply are under pressure.

The competition has moved past the reply. The independent vendors now compete on what happens after it: tasks, coordination with your team, voice, upsells and changes written back to the PMS. "Agentic" is the label most use for this. The test is whether a tool can read context, apply your policies and act across your systems, which we break down in agentic AI for short-term rental operations.

Operations is the next frontier. Guest messaging is largely solved for routine questions. The newer layer is field operations: two-way coordination with housekeepers, re-planning staff days, and scoring every stay to find what to fix. Scheduling tools like Breezeway plan the day. Few tools yet adapt it.

Prices are converging. Where they're public, messaging autopilot sits at roughly $7 to $18 per listing per month, with full suites at $30 to $48. Watch for usage credits, upsell commissions and annual commitments.

Keeping the AI current is the next dividing line. Most built-in AIs rely on a knowledge base and rules your team maintains. That works for a small portfolio, but the upkeep grows with every property. Some independent tools now learn from past conversations, save the answers your team gives and remember corrections. Those claims are hard to check from a sales page, so test them in a trial.

Measurement is the weak point. Almost every vendor claims 70 to 90%, and none publishes a full method. Independent reviews are thin, often fewer than 25 per product, and many comparison articles are written by vendors. The only way to know is to measure it on your own conversations.

Before you sign anything

• Ask for a trial on your own listings. Two weeks is usually enough.
• Ask what the AI won't do, and how you change that.
• Check the contract. Notice periods and annual terms come up repeatedly in reviews.
• Check the data terms. Ask whether your guest conversations are used to train models, and whether you can opt out.
• Decide on disclosure. In the EU, the AI Act expects people to be told when they're dealing with an AI system. Elsewhere, guests generally respond better to openness than to finding out later.

For the full list, see ten questions to ask any vendor, and for the problems that tend to appear after go-live, why AI guest messaging goes wrong.

Sources

• Guesty ReplyAI Autopilot launch: press release, April 2026 · Guesty pricing
• Hostaway AI Auto-Reply: Travolution · Hostaway AI
• Hospitable: AI auto-replies help article · usage figures
• OwnerRez Rezzy: ownerrez.com/rezzy
• Conduit: pricing · short-term rentals
• Aeve: Guesty Marketplace listing
• Boom: funding announcement
• Besty AI: funding coverage · STR Specialist review
• HostBuddy: Capterra reviews · STR Specialist review
• Enso Connect: ensoconnect.com · Trustpilot
• Akia: Track partner page · G2