Skip to main content

Short-Term Rental Automation

Paying a manager a cut of every booking to send the same six messages?

Shepard Consulting builds AI operations systems for short-term rental owners: scheduled guest messaging from booking to checkout, door codes that release only when a reservation is confirmed, cleaner confirmation checks before every turnover, and a bookkeeper that records expenses per property. Anything involving money, safety, or a judgment call goes to a human.

Get the free AI Roadmap

Everything happens by email. Replies within 24 hours from matt@shepardconsulting.ai.

The Problem

What is actually going on

Booking confirmation. Pre-arrival. Day of. Day after. Checkout. Thanks for staying. That is most of the guest communication on most stays, and it is the same every time.

The hard part of running a rental was never those six messages. It is the 11pm door code that does not work, the cleaner who did not confirm, and finding out in April what the place actually made last year.

What You Get

What is included

  • Scheduled guest messaging

    Six touchpoints from booking to post-stay, sent on the booking platform thread. Guest questions get a drafted answer for approval until the system has earned automatic sending on that property.

  • Door codes with gates

    A code goes out only when the reservation is confirmed and the code actually exists on the lock. Once a guest has a code, it does not change on them mid-stay.

  • Turnover checks

    Every cleaning gets checked for a confirmed cleaner a week out and again the day before. Silent when it is covered. Loud when it is not.

  • Escalation rules

    Refund requests, pets, damage, safety, anything about money. The system drafts and a person decides. It never issues a refund.

  • Books per property

    A digital bookkeeper records every bill and receipt against the right property as a draft for you to approve.

  • Built around your stack

    Mine runs on Hospitable for channels, Turno for cleaning, and Seam for smart locks. Other tools get scoped per owner.

How It Works

Three steps, all by email

  1. Tell me what you run and where it hurts

    Number of doors, booking platforms, lock type, and who cleans. By email.

  2. Start supervised on one property

    Every message is a draft you approve. You see exactly what it would have sent.

  3. Turn on automatic sending one property at a time

    Only after it has proven itself on the one before it.

I Try It On Me First

Where this has already been proven

I built this for my own rentals because I was tired of being the dependency. It runs in production on my doors today. I turn on automatic sending one property at a time, after the system has proven itself on the one before, and I would do the same with yours.

Shepard Consulting builds the system. It does not manage properties. You or your manager still run the place, with most of the daily noise gone.

Before any build starts, we write down exactly what done means and we both sign it. I keep working until every item on that list functions. No cutoffs, no close enough.

I am Matt Shepard, a licensed general contractor in Colorado and the owner of Shepard Consulting. Every system I sell is one I run in my own businesses. Read the case studies.

Common Questions

Short-Term Rental Automation: questions people ask

Does this replace my property manager?

It replaces the repetitive part of the job: messages, reminders, checks, and bookkeeping. Someone still has to own the cleaners, the guests with real problems, and the hard calls. For a lot of owners that someone can be them again once the daily noise is gone.

Do you manage short-term rentals?

No. Shepard Consulting builds and maintains the automation. You or your manager operate the property.

Which platforms does it work with?

My own system runs on Hospitable, Turno, and Seam-connected smart locks, with Airbnb as the main channel. If you use different tools, I scope that before quoting.

What happens when a guest asks something unusual?

It drafts an answer from your property information and sends it to you for approval. If the message involves money, safety, a pet, or anything it is not sure about, it escalates instead of guessing.

How much does short-term rental automation cost?

It depends on the number of properties and the tools involved. Send a message with your setup and I will reply with a quote by email.

Related

AI Digital Employees

An AI assistant, bookkeeper, or operations manager with a job description, a goal, and hard limits on what it can never do.

See how it works

AI Business Automation

Accounts payable, invoice follow-up, timesheets, marketing content, and lead follow-up that run without you keying anything in.

See how it works

Tell me what you need fixed

Send a message with your business name and what is not working. I will reply by email with what I would do and what it costs.

All services

Last updated September 20, 2026.