Running on Auto-Pilot: The PMS Challenge Facing STR Hosts & the Solutions That Work

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If you’ve ever found yourself replying to a 1 a.m. message about how to connect to the Wi-Fi, even though it’s in your guidebook, then you’re not alone.

Many short-term rental (STR) hosts feel like they’re running two jobs: one as a hospitality manager, and the other as a 24/7 help desk. While automation tools promise freedom, not all deliver on that dream as you're still answering repetitive questions, double-checking schedules, and stepping in to calm guests when things go sideways.

So when hosts gets on Forums asking question like:

“What’s the best PMS for fully automated and auto-pilot guest communication?”

The host is really voicing a question that’s on every host’s mind:

Is there a property management system that can actually manage guest messages without me being glued to my phone?

Let’s unpack the current PMS landscape and spotlight the tools that truly deliver.

The PMS Problem: Not All Automation Is Equal

Let’s be honest, the STR tech stack is crowded. There are dozens of Property Management Systems out there promising to automate your business and free up your time. Most STR hosts use a PMS to manage the basics: bookings, calendar syncs, messaging templates, and maybe a few team coordination tools. But when it comes to true hands-free automation, especially around guest communication, things get tricky.

Some platforms excel at pre-scheduled messages. Others thrive when it comes to guest messaging, all however, PMS platforms are created equal.

Some are great at sending pre-scheduled messages (like check-in instructions) but fall short when it comes to real-time guest support. Some offer slick AI tools, but only if you’re willing to switch platforms entirely, Others integrate with third-party tools like Touch Stay or guidebooks. But few truly allow you to step away without worry. That’s where AI-forward tools like Besty AI are stepping in, offering advanced chatbot support designed to mimic human responses and take guest communication to the next level. However, many of these newer AI tools don’t integrate well with the PMS you’re already using.

And that brings us to the key question: What PMS tools can actually deliver on the promise of full automation without sacrificing service quality?

What Is a PMS, Really?

A Property Management Software (PMS) acts as the central control panel for your STR business. It can:

Manage bookings across platforms
Automate guest messaging
Coordinate cleanings and tasks
Collect payments
Centralize communication
Analyze performance metrics

Some PMS tools now go even further with AI-powered guest communication, upselling features, and real-time problem resolution.

Let’s look at the top PMS options STR hosts are talking about, and what each one brings to the table.

Comparing the Leading PMS Platforms for Guest Communication

1. Hospitable

(Best for message automation and proactive communication)

Hospitable is a favorite among STR hosts for good reason—it’s simple, intuitive, and powerful when it comes to guest messaging. While it doesn’t currently integrate with Besty AI, its own AI features are worth noting.

Key Features:

AI-suggested replies based on past guest interactions
Knowledge Hub to store answers and automate FAQ responses
Custom message templates triggered by booking events (check-in, checkout, etc.)
Unified inbox for Airbnb, Vrbo, Booking.com, and direct bookings
Proactive communication drip (send info before guests ask)
Touch Stay integration to pull guidebook answers into replies

🧠 Best for hosts who want smart automation without leaving the Hospitable ecosystem.

Lodgify + Besty AI

(Best for fully automated guest communication and AI-enhanced replies)

Lodgify recently added integration with Besty AI, creating a powerful combo for hosts who want to go hands-off. Besty uses natural language processing to respond to guest questions instantly, 24/7.

Key Features:

AI-powered chatbot that handles real-time guest messaging
Dynamic upselling (early check-in, mid-stay cleans, late check-out)
Custom conversation flows tailored to each property
Sentiment analysis to detect urgency or dissatisfaction
Smart inbox and message routing to avoid duplicates
Integrated booking engine and website builder

💡 Best for hosts who want auto-responses, upselling, and deep automation in one platform.

Canary Technologies

(Best for boutique hotels and multi-unit STR operators)

Canary is designed for hotels but is now gaining popularity with STR managers running large portfolios or boutique brands. While it doesn’t cater specifically to Airbnb-style hosts, its AI tools are robust.

Key Features:

Contactless check-in and check-out
Real-time guest messaging via SMS or WhatsApp
Digital tipping platform for staff and cleaners
Upselling tools for monetizing add-ons
Identity verification and fraud detection
PCI-compliant payment system

💼 Best for hosts managing 10+ units or luxury STRs who want hotel-level tech.

Still Not Sure What’s Right for You?

Here’s a quick breakdown to help:

PlatformBest ForAI CapabilitiesUpsellingCustom Guidebook IntegrationHospitable1–10 units, fast message automationAI-suggested replies + Knowledge HubLimitedYes (Touch Stay)Lodgify + Besty5+ units, scaling operations, 24/7 automationAdvanced AI chat with sentiment detectionYesYesCanaryHotels or 10+ unit boutique STRsHotel-grade messaging, check-in AIYesNo

Insights from STR Forums

Discussions across various STR forums have surfaced some valuable insights:

Some hosts still rely on virtual assistants to fill the gaps where automation falls short
Touch Stay continues to be a go-to digital guidebook tool that helps reduce guest questions
A smart mix of automation and proactive messaging can cut guest communication by up to 80%
Even with AI on the rise, it’s clear that human support still wins when it comes to empathy and handling those tricky, one-off situations

Don’t Settle for “Good Enough”

The days of manually answering the same guest questions over and over are behind us, if you choose the right tools. Whether you want full AI automation or a reliable hybrid setup, the PMS you use should be working for you, not the other way around.

💡 Your ideal tech stack might look like: