Mailopoly vs Guesty

Side-by-side comparison of features, pricing, and ratings

Analysis reviewed Live tool data as of 2026-09-29
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At a glance

DimensionMailopolyGuesty
Pricing14-day free trial, then paid (no free tier)Free Lite tier for 1-3 listings; paid plans for 4-199 and 200+ listings
Target UsersIndividual professionals & solopreneursVacation rental managers & enterprise operators
Core Use CaseAI email management & inbox organizationAI-driven property management & guest communication
AI FeaturesAuto-sorting (Cleanbox), AI replies in your voice, Poly assistant, key detail extractionAI auto-reply, AI agents, AI bank reconciliation (launched June 2026), review summaries
Integration DepthGmail, Outlook, Yahoo, IMAP, Slack, WhatsApp, ChatGPT, Claude, Microsoft TeamsAirbnb, Booking.com, Vrbo, Expedia, 60+ OTAs, Siteminder, Kigo
Latest NewsOfficial ChatGPT app & MCP support (June 2026)Launched AI bank reconciliation (June 2026)
Try MailopolyTry Guesty
Mailopoly
Mailopoly

Mailopoly is an AI email assistant that folds email and business messaging into one Poly-powered inbox.

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Guesty
Guesty

AI-powered vacation rental management software that syncs listings across 60+ booking channels

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Pricing
Freemium
Freemium
Plans
$6.99/mo or $4.89/mo billed annually
$8.99/mo or $6.29/mo billed annually
$11.99/mo or $8.39/mo billed annually
$17.99/mo founding rate, renews at $24.99/mo
$13.99/seat/mo founding rate (2-seat minimum), renews at $19
$3.50/mo per extra connection
Contact for pricing
Get a quote
Customized offer
Popularity
3 views
7.2k views
Skill Level
Beginner-friendly
Intermediate
API Available
Platforms
WebMobileDesktop
WebMobile
Categories
📥 Email & Inbox Management⚡ Productivity
🏘️ Real Estate & Property
Features
Cleanbox AI inbox filtering with no rules or training required
AI-drafted email replies written in your voice with multiple suggestions
Poly AI assistant for inbox Q&A, summaries and scheduling questions
My Day task list auto-populated from incoming messages
Automatic extraction of invoice amounts, booking details, dates and delivery updates
Bulk unsubscribe tool for clearing recurring noise
Business channel support: Slack, WhatsApp, Instagram, Messenger, Teams, TikTok
X (Twitter) DMs, mentions and replies unified in the inbox on Pro and Business, 100 messages/mo included
Secure @mly.life email delivered entirely inside Mailopoly's encrypted network
PolyBox centralised attachment library with a shared team drive on Business
Multi-provider email support: Gmail, Outlook, Yahoo, Hotmail, iCloud and any IMAP
Mailopoly for Claude and ChatGPT via MCP
Agent Switchboard for AI assistants to send messages and hand off work through Poly
Verified Meta Tech Provider connections for Facebook and Instagram channels
Task assignment and shared calendar events for Business teams
Sync listings in real time across Airbnb, Booking.com, Vrbo and 60+ booking channels
Agentic AI agents that act, decide and execute property management tasks on your behalf
ReplyAI™ generates personalized AI replies to guest messages
Unified Inbox consolidates guest conversations from every channel in one place
Multi-Calendar manages reservations across channels, multi-unit complexes and group bookings
Workflow automation covering the end-to-end guest journey
Guest CRM with pipeline view and owners portal with customizable owner statements
Guest app and user-friendly guest portal for personalized stays
Mobile app for on-the-go management plus Task Management for cleaning and maintenance
Guesty PriceOptimizer™ machine-learning dynamic pricing with per-channel rate strategies
Rate plans, coupons, promotions and advanced fee setup
Guesty Pay™ payment processing plus Stripe, Merchant Warrior and Hyp
Trust Accounting™ for compliant vacation rental hospitality accounting
GuestVerify™ guest screening with AI-powered fraud and chargeback management
AI-powered listing descriptions and AI-driven website content creation
Integrations
Gmail
Outlook
Yahoo
iCloud
Slack
Microsoft Teams
WhatsApp
Facebook Messenger
Instagram
TikTok
Claude
ChatGPT
Airbnb
Booking.com
Vrbo
Stripe
Merchant Warrior
Hyp
Airbnb Quality Dashboard

Who should pick which

  • Solo entrepreneur with 3 email accounts
    Pick: Mailopoly

    Mailopoly centralizes multiple accounts, sorts important emails, and drafts replies, saving hours daily.

  • Vacation rental host with 5 properties
    Pick: Guesty

    Guesty's free Lite tier covers 1-3 listings; upgrading handles 5 properties with unified inbox, multi-calendar, and AI guest messaging.

  • Enterprise property manager (200+ listings)
    Pick: Guesty

    Guesty's enterprise plan offers custom PMS solutions, AI bank reconciliation, and 60+ channel integrations.

  • Freelance writer with high email volume
    Pick: Mailopoly

    Cleanbox and My Day reduce email clutter; AI replies in your voice speed up client correspondence.

  • Host trying to automate guest communication
    Pick: Guesty

    Guesty's AI agents auto-reply based on learned preferences, reducing manual response time significantly.

Frequently Asked Questions

Can Mailopoly manage property bookings?

No, Mailopoly is an email assistant. It can extract booking dates from emails but does not sync calendars with OTAs or manage reservations.

Does Guesty offer a free plan?

Yes, Guesty has a free Lite tier for 1-3 listings with basic features like unified inbox and calendar sync.

Which tool is best for ChatGPT users?

Mailopoly is now an official ChatGPT app (June 2026) and supports MCP, so ChatGPT can directly query your email and tasks.

Does Guesty support dynamic pricing?

Yes, via the PriceOptimizer add-on, which adjusts rates based on demand and market data.

Can I use Mailopoly with any email provider?

Yes, it supports Gmail, Outlook, Yahoo, Hotmail, and any IMAP account.

Is Guesty suitable for single property hosts?

Yes, the free Lite tier is designed for 1-3 listings, providing essential features for small hosts.

Which tool has AI bank reconciliation?

Guesty launched AI bank reconciliation in June 2026 to automate matching transactions to reservations.

Are there security certifications?

Mailopoly is SOC 2 Type II certified; Guesty also follows industry security standards for payment and data handling.

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Explore each tool further

Mailopoly
View Mailopoly reviewMailopoly alternatives
Guesty
View Guesty reviewGuesty alternatives

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Best AI Email & Inbox Management toolsBest AI Real Estate & Property toolsBest AI Productivity tools
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Last reviewed: July 3, 2026