Kevin Musprett

Co-founder & CEO

Jan 9, 2026 – 5 MIN

Best Airbnb Automation Software: A 6 Step Buyer’s Checklist

If you are actively looking for the ‘best Airbnb automation software,” you are usually trying to solve one problem:

You are spending too much time reacting to guest messages and operations, and response delays start risking reviews.

Airbnb’s built in scheduled messages help, but they do not handle real guest conversations end to end. The tools in this category promise a bigger outcome for faster replies, fewer interruptions, and missed inquiries impacting reviews.

This guide gives you:

a buyer’s checklist (what to evaluate before you buy)
a practical way to compare tools
a comparison with top airbnb automation tools in the space (Boring Host, Besty AI, ProhostAI, INTO, HostBuddy)

What “Airbnb automation software” should actually automate

A useful tool should go beyond scheduled templates and help with at least one of these on how to automate airbnb:

Guest replies: handle repetitive questions accurately (wifi, parking, check-in, house rules)
Operational routing: turn messages into tasks, escalations, and assignments
Consistency: keep tone, policy, and instructions consistent across your team
Scale: reduce workload as listings increase, not increase it

Many vendors label this “autopilot.” The important part is how safe it is.

Quick competitor comparison (as of Jan 10, 2025)

This is not a “winner” list. It is a fit map based on what each product publicly emphasizes.

Product	Best fit for	How it works (high level)	Notable public positioning
Boring Host	PMs scaling across channels who want safe AI autopilot plus unified inbox	AI autopilot replies with confidence gating, unified inbox, ai phone agents, upsells, guidebooks	Built for multi-channel guest comms and operations at 30+ listings
Besty AI	Operators who want autopilot messaging plus unified inbox and journeys	Autopilot messaging with escalation when not confident, unified inbox, guest journeys with multi-channel delivery	Strong emphasis on autopilot, unified inbox, upselling, and journeys
ProhostAI	Hosts who want an all-in-one AI assistant with messaging plus tasks	AI replies and autopilot, AI task manager from messages and reviews, integrations list published	Positions as all-in-one assistant with messaging, tasks, guidebooks, upsells
INTO	Guesty-based teams who want AI inside the Guesty inbox	Chrome extension inside Guesty inbox, AI reply suggestions, also offers fully managed guest services tier	Strong “no new platform” Guesty workflow angle; tone improvement features
HostBuddy	Hosts who want AI messaging with unified inbox options	Markets AI messaging, documentation and partners describe WhatsApp and OpenPhone inbox linking	Emphasis on unified communication hub and WhatsApp/OpenPhone integration

The buyer’s checklist (use this to evaluate any platform)

1) Answer quality: where does it pull the truth from?

Ask: “What sources does the AI use to answer?”

Minimum acceptable sources:

listing details and policies
reservation context
your knowledge base or house manual

2) Safety: does it have confidence gating and escalation?

This is the difference between automation that helps and automation that causes problems.

You want:

send automatically only when confident
escalate to a human when not confident
an audit trail of what was sent and why

3) Channel coverage: where can it respond?

If most of your guest messages live only in Airbnb, a basic tool might be enough.

If guests message you across channels (SMS, WhatsApp, email, phone), you want:

a unified inbox or a way to keep context linked to the reservation

4) PMS and integration fit: will it connect to your stack?

Do not buy before confirming your PMS and channels are supported.

5) Team workflows: can you run it with multiple operators?

If you have a team, you want:

assignments or routing
internal notes
a clear handoff workflow when AI should not send

6) Commercial model: does pricing scale fairly with listings?

Ask:

Is pricing per listing, per message, per minute, or flat fee?
Is “autopilot” included or an add-on?

How to choose based on your situation

If you manage 1 to 5 listings

Start simple:

Airbnb scheduled messages and templates
one clean digital check-in guide
Then evaluate software only if messaging is still a daily drag.

If you manage 5 to 30 listings

Your biggest leak is usually operational coordination plus inconsistent replies.

Prioritize:

unified inbox and routing
guardrails (draft-only for risky topics)
PMS fit

If you manage 30+ listings

You need two things:

reliable autopilot on repetitive conversations
escalation workflows that keep risk low

If you also need multi-channel unification, prioritize unified inbox capabilities and channel integrations.

What to ask on every demo (copy and paste these questions)

“Show me how the AI answers a wifi question, a parking question, and a lock issue using real listing data.”
“What triggers autopilot sending, and what triggers escalation?”
“How do I control tone, prohibited phrases, and policy wording?”
“Which PMS integrations are live today for my exact setup?”
“What happens when the AI is wrong, and how do I review logs?”
“How do you prevent the AI from improvising on refunds, disputes, or safety issues?”

Boring Host is best when you want AI messages on autopilot with guardrails, and you are dealing with multi-channel messaging and a growing portfolio. The practical evaluation test is simple: if your workload is not just scheduled messages, but constant back-and-forth questions plus cross-channel threads, you want a platform designed for unified conversations and safe autopilot.

If you want AI to handle guest questions automatically while staying safe and on brand, see how Boring Host approaches 24/7 guest replies with safe autopilot.

Unified multi-channel conversations (Airbnb, WhatsApp, SMS, and more): If your team is juggling multiple inboxes and you want everything in one place, see how Boring Host connects Airbnb messaging into a single shared inbox.

Built for growing portfolios (clear, scalable pricing): If you’re evaluating cost per listing and how pricing scales as you add properties, see how pricing scales as you add more listings.

FAQs

Is Airbnb’s built-in automation enough?

It is enough for scheduled messages and basic templates. It is usually not enough for real-time Q and A, cross-channel messaging, and scaling beyond a small portfolio.

What is the single most important feature in Airbnb automation software?

Safety guardrails: confidence gating plus escalation.

Which tool is best?

The best tool is the one that matches your PMS, your channel mix, and your risk tolerance. Use the demo questions above to decide.