Filently vs Guesty
Side-by-side comparison of features, pricing, and ratings
At a glance
| Dimension | Filently | Guesty |
|---|---|---|
| Primary Function | Google Drive file organization | Vacation rental property management |
| Key AI Feature | AI reads documents to rename & file automatically | AI agents for messaging, task management, bank reconciliation |
| Best For | Professionals overwhelmed by Drive clutter | Property managers with 4-199+ listings |
| Integrations | Google Drive, Gmail, Google Shared Drives | 60+ booking channels including Airbnb, Booking.com, Vrbo |
| Latest News | June 2026: Guide on auto-saving Gmail attachments to Drive | June 2026: AI-powered bank reconciliation launched |
Choose Guesty if you manage vacation rentals and need AI to automate guest messaging, task management, and reconciliation across multiple channels. Choose Filently if your pain point is a messy Google Drive and you want an AI that automatically renames and files documents with zero setup. They solve entirely different problems, so your decision depends on your primary operational headache.
AI document filing for Google Drive that reads each document, renames it your way and files it in the right folder.
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AI-powered vacation rental software with real-time channel management and ReplyAI guest messaging
Visit WebsiteWhat real users say: Filently vs Guesty
Not marketing copy and not our opinion — a structured sweep of public discussion (reviews, forums, communities and video comments), showing what people praise and what they complain about for each tool.
Filently
No verifiable community signal. We scanned public discussion on Aug 31, 2026 and found posts matching the name “Filently”, but could not establish that they are about this product rather than something else sharing its name. Rather than publish a score built on the wrong subject, we publish none.
Guesty
42 mentions across 4 sources · 36% positive — critical (averaged across 4 sources)
Hacker News, YouTube, Product Hunt, Bluesky
What users praise
- • AI agent automates guest messaging based on learned preferences (ReplyAI).
- • Multi-calendar sync across 60+ booking channels including Airbnb and Vrbo.
- • Free Lite tier for up to 3 listings provides a risk-free trial.
- • Open API and MCP server allow custom integrations via open-source tools.
What frustrates them
- • Pro and Enterprise pricing not publicly disclosed — reported $65 per property.
- • Channel-specific pricing not possible; rate changes sync everywhere.
- • Custom automation limited compared to Yardi/WorkBeaver according to users.
- • Some users report reliability issues post-2023 acquisition.
Researched Jul 16, 2026
Who should pick which
- Vacation rental manager with 10 listingsPick: Guesty
Guesty is built for property managers; its unified inbox, multi-calendar, and AI agents save hours on guest communication and task management across channels.
- Virtual assistant organizing multiple client Google DrivesPick: Filently
Filently auto-files documents per client conventions, reducing manual sorting. The Team plan supports multiple clients, and it’s built for Google Drive.
- Solo host with 2 properties on Airbnb onlyPick: Guesty
Guesty’s free tier provides basic multi-calendar and AI messaging, which can help a solo host grow without upfront cost, though Filently doesn’t help with rental ops.
- Accountant needing to organize client invoices in DrivePick: Filently
Filently reads invoice content, renames by vendor/date, and files into client folders. Its guide for accountants (May 2026 news) confirms this use case.
- Enterprise operator with 200+ propertiesPick: Guesty
Guesty’s enterprise features, AI reconciliation, and 60+ channel integrations are essential for scaling. Filently lacks the operational depth.
Frequently Asked Questions
Filently vs Guesty: which should you choose?
Choose Guesty if you manage vacation rentals and need AI to automate guest messaging, task management, and reconciliation across multiple channels. Choose Filently if your pain point is a messy Google Drive and you want an AI that automatically renames and files documents with zero setup. They solve entirely different problems, so your decision depends on your primary operational headache.
Can Guesty automatically file Google Drive documents?
No, Guesty focuses on rental operations, not file management. For Drive organization, Filently is the right tool.
Does Filently help manage vacation rental bookings?
No, Filently is strictly for Google Drive file organization. It cannot sync calendars, manage guests, or integrate with booking channels.
Which tool is more affordable for a single user?
Filently offers a free Personal plan (50 docs/month) and a $19/month Pro plan. Guesty’s free tier is limited but may suffice for 1-3 listings; however, add-ons cost extra.
Do either of these tools integrate with Dropbox or OneDrive?
No, Guesty integrates with 60+ booking channels but not cloud storage. Filently only supports Google Drive and Gmail (Dropbox/OneDrive on roadmap).
Which tool is better for AI-powered automation?
Both use AI, but for different tasks. Guesty automates guest messaging, task management, and reconciliation. Filently automates file renaming and filing.
Is Filently GDPR compliant?
Yes, Filently is GDPR compliant, EU-based, and does not store data—no copies kept. It also has CASA Tier 2 security certification.
Does Guesty offer a direct booking website?
Yes, Guesty includes a branded direct booking website builder (basic free, advanced add-on).
Can I use Filently for bulk processing of old files?
Yes, Filently can handle bulk processing your existing Drive backlog, with no size limit on uploads, but file size limit applies per document (100 MB on paid plans).
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Last reviewed: July 2, 2026