Best AI Tools for Guesty Users in 2026

Guesty is a PMS. A good one. It handles calendar sync, owner statements, channel distribution, and reservations across 25+ booking platforms. What it does not handle — and was never designed to handle — is everything that happens when a guest picks up the phone, sends a message at 11 PM, or books a stay with a gap night on either side.

That is where AI tools come in. This guide covers the six platforms Guesty users are actually considering in 2026: what each one does, what it costs, where it wins, and where it falls short.

Why Guesty Users Need AI on Top

Guesty's messaging templates automate confirmations and pre-arrival instructions. Useful. But a template cannot answer "Can I bring my dog?" for a property-specific policy it has never seen. It cannot answer a phone call. It cannot detect a gap night and offer the departing guest an extension at a discount.

The gap between "automated messaging" and "AI operations" is wider than the product names suggest. A template fires on a schedule. An AI system reads context, generates a response, and adapts.

Guesty users building serious operations portfolios — 20+ properties, multi-market, high guest communication volume — hit the template ceiling fast. The tools below are how they break through it.

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1. Dimora AI

What it does: AI operations layer with 6 integrated modules — Voice AI (24/7 AI receptionist), Inbox AI (multi-agent system handling guest messages), Revenue Engine (automated upsells), AI Learning (golden example feedback loop), Payment Audit (daily balance scans), and Dashboard.

The Guesty integration: Dimora connects to Guesty via API and reads live reservation data in real time. When a guest calls, the system matches their phone number against active Guesty reservations before the call greeting ends. When a draft goes out, it uses current check-in dates, property-specific notes, and door codes directly from Guesty — not a stale copy.

Real production numbers: Desert Sol Real Estate, 130+ properties in Palm Desert, California. 1,800+ guest calls handled by Voice AI. 6,300+ inbox drafts generated (under 10 seconds each). 470+ early/late checkout and gap night offers sent. Live since Q4 2025.

Pricing: $6/property/month (Essential), $9/property/month (Pro), $12/property/month (Enterprise). 14-day free trial, no credit card required. That is $3,000-$6,000/year for a 50-property portfolio — compared to $25,000-$40,000 for a VA doing the same work.

Who it's for: Property managers on Guesty with 10+ properties who want AI handling calls, messages, and upsell revenue automatically. Strongest fit for operators with high call volume or multi-channel inbox load.

Limitations: Not a hotel tool. Designed for vacation rental managers. If you manage corporate apartments or boutique hotels, the feature set may not map to your use case.

Internal links: Guesty integration details | Dimora vs Akia comparison | Dimora vs Duve comparison

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2. HostAI (Conduit)

What it does: AI messaging assistant for vacation rental and hotel operators. Handles guest communication drafts across channels, learns from manager behavior over time.

The Guesty integration: Integrates with major PMS platforms including Guesty. Reads reservation data to contextualize message drafts.

Pricing: Not publicly listed. Enterprise-forward pricing model. Demo required for quotes.

Who it's for: Larger teams that want AI-assisted messaging with a managed onboarding process. HostAI targets enterprise property management groups.

Limitations: Does not include Voice AI (no AI receptionist). No gap night detection or automated upsell system. No Payment Audit module. The focus is on inbox communication, not full operations automation. If you need to automate calls or revenue, you will need additional tools.

Honest take: HostAI is solid for inbox AI. The gap is on the voice and revenue sides. If your primary pain is message volume, it is a legitimate option. If you also need 24/7 call handling and automated upsells, you are looking at assembling multiple tools.

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3. Duve

What it does: Guest experience platform for hotels and vacation rentals. Digital guidebooks, check-in flows, upsell marketplace, guest communication. Focused on the pre-arrival and in-stay experience.

The Guesty integration: Official Guesty integration. Reads reservation data for personalized guest communications and pre-arrival flows.

Pricing: Pricing available on request. Typically structured as a per-property monthly subscription with tiered feature access.

Who it's for: Operators who want to improve the guest experience layer — digital check-in, branded guidebooks, pre-stay upsells. Hotel and boutique rental operators who want to look more professional at guest touchpoints.

Limitations: Not an AI operations layer. Duve is guest experience software. It does not handle inbound phone calls, does not run a multi-agent inbox AI, and does not have an AI learning feedback loop. The upsell features are opt-in from guests (they browse an upsell menu) — not automated outreach to eligible guests.

Honest take: Duve wins on guest-facing polish. If your portfolio targets guests who value a premium digital experience, Duve's guidebooks and check-in flows are genuinely good. The operational automation story is different — Dimora and Duve are targeting different pain points.

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4. Akia

What it does: AI messaging and guest communication platform. Strong hotel focus with vacation rental support. Automated messaging, two-way SMS, digital check-in, upsell automations.

The Guesty integration: Integrates with Guesty. Pulls reservation data for personalized automated messages.

Pricing: Not publicly listed. Property-based pricing available via demo.

Who it's for: Hotels and hotel-adjacent property managers who want automated messaging with SMS support. Akia is stronger in the hotel segment than in the vacation rental segment.

Limitations: No AI receptionist for voice calls. Messaging automations are more template-driven than AI-generated. Not built around the vacation rental–specific use cases (turnaround-aware upsells, gap night detection, property-specific HOA rules in AI responses).

Honest take: Akia built for hotels, then expanded. For pure vacation rental operations, tools built for STRs natively — like Dimora — tend to handle edge cases better. Akia is a reasonable choice if you run a hybrid hotel/vacation rental portfolio and want messaging consistency across both. See Dimora vs Akia comparison for a detailed side-by-side.

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5. Breezeway

What it does: Property operations and cleaning management. Task management for cleaners and maintenance, property inspections, cleaning quality scores, inventory management.

The Guesty integration: Deep Guesty integration. Reads reservation data to automatically schedule cleaning tasks, track turnaround completion, and alert managers to maintenance issues.

Pricing: Available via demo. Per-property monthly subscription.

Who it's for: Operations managers who want to systematize cleaning coordination, maintenance tracking, and property inspections. Especially valuable for operators who self-manage cleaning crews rather than outsourcing.

Limitations: Not a guest communication tool. Breezeway does not handle phone calls, inbox messages, or upsell automation. It handles what happens to the property, not what happens between the property and the guest.

Honest take: Breezeway solves a real problem and solves it well. Many Guesty users run Breezeway alongside an AI communication tool — the two are genuinely complementary. Breezeway handles the cleaning/operations side. Dimora handles the guest communication and revenue side.

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6. Operto

What it does: Smart device management, guest access, digital check-in, and property monitoring. Integrates with smart locks, thermostats, noise sensors, and access control systems.

The Guesty integration: Integrates with Guesty. Syncs reservations to trigger access code generation, smart device control, and automated check-in flows.

Pricing: Property-based pricing, available via demo.

Who it's for: Operators who want automated smart device management — locks that generate unique codes per reservation and expire automatically, thermostats that adjust for arrivals and departures, noise alerts. Strong for tech-forward operators who want remote property control.

Limitations: Not a guest communication AI. Operto does not handle inbound calls, generate inbox drafts, or run an upsell engine. It manages devices and access, not conversations.

Honest take: Like Breezeway, Operto is a complementary tool rather than a competitor to AI communications platforms. Operto handles physical access and device automation. Dimora handles what guests say and what revenue you can capture from their stay.

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The Right Stack for Guesty Users

Most mature Guesty operations run a stack of 2-3 specialized tools, not one platform that does everything. A common pattern:

• Guesty — PMS, reservations, channel distribution
• Dimora AI — Voice AI, Inbox AI, Revenue Engine, Payment Audit
• Breezeway or Operto — Cleaning operations or smart device management

The tools that try to do everything tend to do nothing exceptionally well. The tools that specialize — and integrate cleanly with Guesty — deliver more value per dollar.

For operators whose primary bottleneck is guest communication volume (calls, inbox messages, upsell revenue), Dimora AI is purpose-built for that layer. For operators whose primary bottleneck is cleaning coordination or smart device management, Breezeway or Operto serve that need better.

The honest question is: where are you losing the most time and money? Start there.

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Quick Comparison

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All Dimora AI numbers reflect production data from Desert Sol Real Estate, 130+ properties, Palm Desert, California. Other vendor capabilities based on published features and public documentation current as of February 2026.