How to read this guide
Most "best software" lists rank ten tools against each other as if they did the same job. They do not. A Guesty subscription and a Turno subscription solve different problems, and the honest comparison is by layer:
- The PMS: reservations, calendars, channel sync. Everything else plugs into it.
- Guest messaging: answering people on Airbnb, Vrbo, Booking.com, WhatsApp, SMS, and email.
- Cleaning and maintenance coordination: turnovers scheduled, verified, and paid.
- Dynamic pricing: nightly rates that follow demand.
- The AI operating layer: agents that read the guest message, answer it, and create and chase the work it implies across the other four layers.
Two disclosures before the rankings. First, Trellis builds layer five, so read that section knowing who wrote it; the other layers name competitors and tools we do not sell. Second, I run my own vacation rental portfolio in the Florida Keys and Miami, on Guesty, so the PMS and pricing sections come from someone who pays these invoices. Everything about other vendors comes from their public pricing pages and independent reviews, each linked with the date we read it.
Layer 1: the PMS
The PMS decision matters more than any other because switching later is painful and everything else syncs through it.
| PMS | Published entry price | Strongest at | Watch out for |
|---|---|---|---|
| Guesty | Quote only | 10 to 1,000+ units, 100+ channel integrations on Pro | Opaque pricing; built for scale, priced for it (StaySTRA) |
| Hostaway | Quote only | Professional operators, marketplace of 200+ integrations | Also quote-based; ask for the all-in number |
| Hospitable | From $29/mo, free Essentials tier | Solo hosts and portfolios under 10 with strong messaging automation | Outgrown by complex ops teams (StaySTRA) |
| OwnerRez | From $88/mo | Direct booking depth, accounting; highest ratings of the four (5.0 on G2, 4.9 on Capterra per StaySTRA) | Steeper learning curve, price at small scale |
| Lodgify | Tiered | The best website builder of the group; direct-booking-first hosts | Thinner on large-portfolio operations (Rental Duel) |
The short version: under 10 units, Hospitable or OwnerRez depending on whether messaging or direct bookings matter more. From roughly 20 units up, the realistic candidates are Guesty and Hostaway, and the deciding factors are your channel mix, your market's integrations, and the quote each gives you. Trellis connects to all five and to every PMS available through Calry, so the PMS choice does not lock you out of the agent layer; the full list is on our integrations directory.
Layer 2: guest messaging AI
Every PMS above ships some message automation. The dedicated messaging tools go further, and they separated into price tiers in 2025 and 2026:
- HostBuddy is the budget pick at $7 to $12 per property per month: AI replies through your PMS, action items logged for your team, tier caps on history and journeys (hostbuddy.ai/pricing).
- Conduit (formerly HostAI) sells credit-based packages from $18 per unit per month, with voice AI in the base tier and tasks and dispatch reserved for the $48 Full Suite (conduit.ai/pricing).
- Besty bundles messaging, upsells, and operations under quote-based pricing tied to a revenue share (Rentals United partner listing).
- Enso Connect focuses the guest journey: digital check-in, upsells, and a guest web app alongside the AI inbox.
We compared the first three line by line in Hostbuddy vs HostAI vs Besty. The pattern across all of them: the affordable tier answers messages, and the moment a message becomes work for a cleaner or a vendor, you either pay for a higher tier or do it yourself in another tool.
Layer 3: cleaning and turnover coordination
There are two models here, and they are priced differently enough that the wrong pick is expensive. Marketplaces solve labor sourcing; SaaS tools organize the staff you already have (STR Tech Report).
- Turno: the marketplace. Free if your cleaners come from it, $10 per property per month if you bring your own. The right call when finding cleaners is the problem (turno.com/pricing).
- Breezeway: the operations platform. Checklists, inspections, work orders, owner reporting; $19.99 per unit under five properties, quote above (breezeway.io/breezeway-pricing). The right call at 15+ doors with your own field team.
- Operto Teams: the budget scheduler at $7 per property per month with a $40 minimum (STR Tech Report).
- Properly: photo-verified checklists for quality consistency (Nightlydata).
Under 8 doors with a cleaner you trust, your PMS's built-in task features probably cover it, a point Nightlydata makes well. We wrote the deeper comparison in Breezeway vs Turno, and if you are weighing Breezeway against an agent-run alternative, the honest version is on Trellis vs Breezeway.
Layer 4: dynamic pricing
PriceLabs, Beyond, and Wheelhouse own this layer, and any of the three beats flat rates or Airbnb's Smart Pricing, which optimizes for booking volume rather than your revenue; StaySTRA's testing puts the third-party advantage at 15 to 36% more revenue for professional hosts (StaySTRA). My own units run on Wheelhouse. Pick by which one covers your market's data best and whose recommendation workflow your revenue manager actually enjoys. This is the one layer an AI operating platform should read from, not replace.
Layer 5: the AI operating layer
This is the layer we build, so judge the framing accordingly.
Layers 1 through 4 share a gap: when a guest message means work, a person carries it across tools. The guest reports a broken shower at 11 pm; someone reads it in the PMS, opens the cleaning tool, creates the task, texts the cleaner, and remembers to tell the guest. Messaging tools draft the reply and stop. Operations tools track the task once a person creates it.
Trellis runs AI agents across the whole stack instead: the agent answers the guest on whatever channel they wrote on, creates the maintenance or turnover task, assigns it from availability, briefs the cleaner or technician on mobile with full property context, and closes the loop back to the guest. Autopilot is earned per channel and per property; agents draft until the team has approved enough replies, and billing does not start until autopilot reaches 70% accuracy. One plan from $749.99 per month, scaled by property count, everything included (pricing).
The honest fit: Trellis is built for management companies running roughly 20 to 2,000 units on a PMS. If you host two units, Hospitable's free tier plus Turno will serve you better and cost almost nothing. If you run 50 units with a coordinator spending their day carrying messages into tasks, the agent layer is the thing that changes your cost structure rather than your tooling.
Stacks by portfolio size
| Portfolio | PMS | Messaging | Cleaning | Pricing | Agent layer |
|---|---|---|---|---|---|
| 1 to 5 units | Hospitable (free tier) | Included in PMS | Turno free tier or PMS tasks | PriceLabs or Wheelhouse | Not yet |
| 5 to 20 units | Hospitable or OwnerRez | HostBuddy if PMS automation runs out | Turno | Any of the three | Borderline; price against a part-time hire |
| 20 to 200 units | Guesty or Hostaway | Replaced by the agent layer | Breezeway, or agent-run tasks | PriceLabs, Beyond, or Wheelhouse | Trellis |
| 200+ units | Guesty or Hostaway | Agent layer with per-property guardrails | Breezeway alongside agents, or agents alone | Revenue manager with a pricing tool | Trellis |
Frequently asked questions
Do I need a PMS under 10 units?
Usually yes, but a cheap one. Channel sync alone (no double bookings across Airbnb and Vrbo) pays for Hospitable's entry tier. What you do not need under 10 units is a paid tool in every layer.
Can one platform really do everything?
No, and be suspicious of any that claims it. The realistic consolidation in 2026 is a PMS as the system of record plus an agent layer that does the coordination work between it and your field team. Pricing stays a specialist tool.
What about Airbnb's own AI features?
Airbnb shipped AI onboarding and listing Q&A in 2026, but it has no native AI answering incoming guest messages; automation there still means third-party software (StaySTRA). And Airbnb tools only cover Airbnb guests.
When does an AI operating layer replace the point tools?
When the cost of the coordinator role exceeds the cost of the layer. Several Trellis customers run Breezeway alongside agents during migration and retire it once the agent-run tasks cover their workflows; others keep it. The deciding number is how many hours a week a person spends turning messages into tasks.
Sources
All retrieved 2026-08-23 unless noted.
- StaySTRA, "The STR Property Management Software Showdown for 2026": https://staystra.com/str-property-management-software-2026-hospitable-guesty-ownerrez-lodgify
- StaySTRA, "Airbnb AI and Automation Features for Hosts in 2026": https://staystra.com/airbnb-ai-tools-hosts-2026
- STR Tech Report, "Top Operations & Cleaning Software for Vacation Rentals in 2026": https://strtechreport.com/resources/top-operations-cleaning-software-for-vacation-rentals-in-2026
- Nightlydata, "STR Turnover Software: Which Tools Cut Same-Day Failures (2026)": https://nightlydata.com/articles/str-turnover-cleaning-coordination-tools-2026
- Rental Duel, "Vacation Rental Software Comparison": https://rentalduel.com/blog/vacation-rental-software-comparison
- HostBuddy pricing (retrieved 2026-08-22): https://www.hostbuddy.ai/pricing
- Conduit pricing (retrieved 2026-08-22): https://www.conduit.ai/pricing
- Turno pricing (retrieved 2026-08-22): https://turno.com/pricing/
- Breezeway pricing (retrieved 2026-08-22): https://www.breezeway.io/breezeway-pricing
- Rentals United, Besty AI partner listing (retrieved 2026-08-22): https://rentalsunited.com/vacation-rental-services/besty-ai/
