Best STR Guest Messaging and Task Software (2026)

Written by Punn Kam, ex-Google AI engineer and Y Combinator repeat founder. He is the co-founder of Conduit, an AI agent platform built for hospitality, serving 300+ hospitality brands in 140+ languages. Last updated October 7, 2026.

For a short-term rental manager who wants guest messaging and task management in one system, Conduit runs both on the same record and can tell the guest when a task changes. Breezeway, Guesty, Hostaway, Hospitable and Operto sell both halves, but a person or a custom integration usually carries the update back. This page ranks seven tools by that return trip.

How did I rank STR guest messaging and task software?

I ranked short-term rental guest messaging and task software on one question: when a guest reports something, how many of the four hand-offs does the tool make without a person? A guest writes that the hot tub is cold, a task gets created, a technician gets it, and the guest hears it is fixed. A tool earns credit for each hand-off its own pages document:

1. The guest message becomes a task without anyone retyping it.
2. The guest's photo lands on the task.
3. The cleaner or contractor receives it on a channel they already use.
4. A change in the task's status reaches the guest.

I read every vendor page on October 7, 2026. If a page says nothing, the tool gets no credit and the table says "not published". We build Conduit, so read its entry with that in mind. Hotels have a different shortlist, covered in the best hospitality operations platforms and the hotel housekeeping software hub.

Which STR tools run guest messaging and tasks together?

Seven short-term rental tools made the list. Conduit documents all four hand-offs, Breezeway and Guesty document the first one well, and Hostaway, Hospitable, Operto and Enso Connect each sell both halves with the connection between them left to rules or to people. Each entry below names the step where the hand-off stops.

1. Conduit

Conduit keeps the conversation and the task in one system, with agents doing the work between them. An agent reads a guest message on Airbnb, Vrbo, WhatsApp, SMS, email or the phone, creates the task with the guest's photos and links it to the property and reservation. Cleaners and contractors get the work order by SMS or email with accept and decline links, and a decline clears the assignment so the task can go to someone else. Task created, assigned, status changed and completed are all triggers, so an agent or a workflow can message the guest, the owner or the next worker when the status moves.

Ops teams shape most of this themselves. Each agent has its own instructions, model, guardrails, per-tool allowlist on each connection, and Autopilot or Copilot mode, with overrides per channel. Workflows are deterministic (conditions, waits, send message, create task, HTTP request), agents can call them as tools, and AI steps can sit inside a workflow. Full Suite, which adds tasks, scheduling and dispatch, starts at $48 per unit per month (pricing).

Watch-outs: Tasks take photos, receipts and checklists with required photos, but not video files. Default assignees are set per property and task category, with no skill matching or proximity routing.

2. Breezeway

Breezeway is an operations platform that added messaging. Breezeway Messaging generates "Smart Tasks" from guest-reported issues, and a message like "we've checked out" can start the turnover. The Concierge add-on recommends a task with the details filled in, and its FAQ says your team adds it in one click. Builders get eleven task webhooks and an image-only Add Task Photo endpoint. Breezeway is free for one property, and its Host Essentials plan starts at $19 per unit per month (the plan description says $19.99), with guest messaging as an add-on; higher plans are quoted on its pricing page.

3. Guesty

Guesty handles the first hand-off with an agent. Its AI agents page lists a Message to Task Dispatcher that "identifies issues within guest messages and creates operational tasks," and a Maintenance Block Agent that blocks the repair window across channels. Cleaning staff work in the Guesty app and upload photos and notes. Guesty includes task management in every plan, starting with Lite for 1 to 3 listings, which Guesty says starts from $9 per listing per month; Pro (4 to 199 listings) and Enterprise are quoted (pricing).

4. Hostaway

Hostaway sells AI messaging and a task manager inside its PMS. The Hostaway AI page says AI Replies "automate up to 90% of guest communication," and its task management covers cleaning, maintenance and inspections, with checklists on the Hostaway Mobile App. Hostaway does not publish a step that turns a guest message into a task or sends a task status to the guest.

5. Hospitable

Hospitable builds tasks from the booking calendar rather than from the inbox. Hospitable Tasks creates tasks "based on check-in, check-out, or mid-stay events," sends them by email, SMS or iCal feed, and lets teammates share pictures of finished jobs. Hospitable's pricing page lists Tasks Manager, the Tasks App and Teammate Payouts on every plan, including the free Essentials plan, with payouts charged per clean. More in our Hospitable review.

6. Operto

Operto sells messaging and tasks as separate modules. Operto Guest sends scheduled SMS, push and email messages, including one triggered by the first door unlock. Operto Teams runs scheduling, maintenance and checklists. The Teams API can create a task with images and documents but has no webhooks, so an outside messaging tool cannot react when a task changes. Our Operto review covers the modules and pricing.

7. Enso Connect

Enso Connect is a guest platform with no task module of its own. Its custom automations can fire "team tasks" as an action, alongside the unified inbox and EnsoAI AutoPilot listed on its home page. Every hand-off runs through rules your team writes and maintains.

How do the seven tools compare on the four hand-offs?

The table compares the seven STR tools on the four hand-offs from the ranking, using each vendor's own pages as read on October 7, 2026. "Not published" means the vendor's pages say nothing either way, so treat it as a question for the demo.

Why does the task status have to reach the guest?

The task status matters because the guest asked for it in a message, and the guest's next message is "any update?". In a short-term rental the person who answers guests is often not the person who sees the cleaner's checklist. Every status change becomes a relay between two people, and the relay breaks at night and on turnover Saturdays.

Conduit treats the return trip as a trigger. A cleaner marks the task done, the task-completed event starts a workflow, and the workflow can wait 10 minutes, check that no newer task is open on the same reservation, and send the guest a message. Breezeway can get you part of the way through its webhooks if someone builds and maintains the listener. Our guide to running messaging and operations in one system shows where the relay breaks.

Should you keep your operations app and connect it instead?

Keeping a dedicated operations app is the right call when your cleaners are trained on it and its checklists are where your quality comes from. Conduit's agents have deep tools into Breezeway (about 49, including creating, updating, commenting on and closing tasks), Guesty, Hostaway and Streamline, so the agent can open and update the task in the system your team already uses. Status changes inside that app still only come back as far as the app's own API lets them, so test that path before you commit.

Where Conduit is heading is background agents that understand scheduling, notice a cleaner called in sick, and rework the day. Conduit has not shipped that agent. Today the pieces are staff availability and time off, a schedule grid with conflict detection, and agent tools that reassign tasks and set due dates.

FAQ

The questions below cover short-term rental software that sells guest messaging and task management together. The answers use vendor pages as read on October 7, 2026, with "not published" where a vendor says nothing. Plans and prices in this category change often, so recheck the linked pages before you sign.

What short-term rental software has both guest messaging and task management?

Conduit, Breezeway, Guesty, Hostaway, Hospitable and Operto all sell guest messaging and task management, and Enso Connect can create team tasks from its automation rules. They differ most after the task exists, especially in whether a status change reaches the guest without a person relaying it.

Which STR software messages the guest when a cleaning or repair task is done?

Conduit can, because task created, status changed, assigned and completed events are triggers that start an agent or a workflow, and that agent or workflow can send the guest message. The other tools on this list either leave that update to a person or to an integration you build on their webhooks or API.

Can AI create tasks from guest messages in a short-term rental?

Yes. Conduit's agents create tasks from conversations, Guesty lists a Message to Task Dispatcher agent, and Breezeway Messaging generates Smart Tasks from guest-reported issues. Breezeway's Concierge add-on recommends a task that your team adds in one click.

How do cleaners get tasks without installing a new app?

Conduit sends work orders by SMS or email with accept and decline links, and the cleaner's answer updates the task. Hospitable sends tasks by email, SMS or iCal feed. Breezeway, Guesty, Hostaway and Operto Teams describe their own staff apps.

How much does STR software with messaging and tasks cost?

Conduit's Full Suite, which includes tasks, starts at $48 per unit per month, and its Startup plan is $899 per month for 0 to 25 units. Breezeway is free for one property, with Host Essentials from $19 per unit per month and guest messaging as an add-on. Guesty Lite starts from $9 per listing per month with tasks included, and Hospitable has a free Essentials plan.

Should a property manager keep Breezeway and add a messaging tool instead?

Keeping Breezeway makes sense when the field team already works well in its app. Conduit connects to Breezeway with about 49 agent tools, including creating, updating and closing Breezeway tasks, so the guest conversation and the Breezeway task can stay linked without switching the field team.