Kissimmee, Florida · English & Français

Booking, rental and guest systems built for Kissimmee

Vacation rentals, property management, rental counters and tour operators all run on the same four things: what is available, who signed what, whose deposit is held, and whether the guest has been answered. We build the system that keeps those four in agreement — in English and in French.

(407) 737-9933 — Cyrus or Tristan. On parle français aussi.

Booking hub, from

$2,900

Units or vehicles, bookings, contracts, deposits and guests on one screen. Plus $190/mo to run it.


Or start with one process, from

$690

Deposits, confirmations or the contract that chases its own signature. Fix one thing first and see whether it was worth it.

Where a booking business leaks

Follow one reservation from enquiry to checkout and you can usually point at the four places it goes wrong. They are the same four whether you rent a house, a car or a seat on a tour.

Availability lives in three places

A calendar, a listing channel and someone's head. When they disagree you either double-book and apologise, or block a unit that was free and lose the night.

The contract is chased by hand

Rental agreement, house rules, driver details, the extra insurance question. Someone emails it, someone forgets, and the guest arrives unsigned.

Deposits are tracked in a spreadsheet

Taken on one system, released on another, remembered in a third. The argument three weeks later is always about a number nobody wrote down properly.

The guest asks at 11pm, in French

Gate code, check-in time, where to park the van, is there a crib. Every one of those has a written answer already — just not anywhere the guest can reach.

Say you manage twenty units and each turnover costs twenty minutes of message-writing, deposit-checking and calendar-fixing. That is a working day a week, gone, before anything goes wrong. We put your own figures into that sentence on the first call — and if the arithmetic does not justify a build, we say so.

What we build here

Pick one, or have the lot on one screen. Start with the thing that woke you up last week.

One availability picture

Units, vehicles or tour slots with their real state: booked, held, blocked for maintenance, out of service. One screen everyone reads, instead of three that disagree.

Which listing channels can be kept in sync automatically depends on the channel. We check yours before quoting.

Contracts that chase themselves

The agreement goes out the moment the booking is confirmed, with the guest's details already filled in, and asks again if it is not signed. Your wording, your terms.

Signed copies filed against the booking, not in an inbox.

Deposits and payment links

A payment link with the booking attached, the balance requested on schedule, and the deposit's state visible against the reservation — held, released, kept.

Your payment processor stays yours. We do not touch the money.

Guest messages on a schedule

Booking confirmed, arrival instructions the day before, gate code and directions on the day, checkout note, review request after. Written once, sent every time.

In English or French, chosen by the guest.

Turnovers and the people who do them

Checkout triggers the clean, the crew gets the address and the window, and you find out it was done — instead of finding out it was not, from a guest.

Pool, air conditioning and repair jobs work the same way.

Owner statements, if you manage for others

Nights, rate, fees and costs per unit, assembled from the same records you already keep, and sent on the same day every month in the same layout.

Owners can be given their own view instead of emailing you.

Put the lot on one screen and it becomes a business hub. Fix a single chore and it is one piece of task automation. Both pages spell out the scope and the price.

English and French, on the same system

Kissimmee hosts visitors from everywhere, and plenty of the people who own and manage units here are not native English speakers either. Most software in this industry treats a second language as a translation job you pay for later. We treat it as part of the build, because both founders speak both.

Le devis, le contrat et le site peuvent être en français. So can the phone call — you are talking to Cyrus or Tristan, not to a translation service.

  • A booking flow and website a guest can switch languages on.
  • Confirmations, arrival instructions and checkout notes in either language.
  • Rental agreements and house rules in both, side by side.
  • An assistant that replies in the language the guest wrote in.
  • Calls, quotes and training with us in English or in French.

Who we build for

This is the closest fit to what we do. Rental counters and rental units are the businesses these systems were shaped around in the first place.

Car rental

Bookings, contracts, deposits and fleet availability in one place.

Availability, the contract and the deposit have to agree at the counter, every time.

Apartment rental & sales

Applications, leases, renewals and tenant requests without the inbox.

Units, turnovers, deposits and the guest who arrives at midnight.

Real estate

Listings, viewings, offers and the paperwork that follows them.

Owners buying and selling the units the rest of this list runs.

Finance & insurance

Client intake, documents, signatures and reminders, handled properly.

Intake, documents and signatures for people who are rarely in the room.

Trades & field work

Quotes, jobs, work orders and invoices that stop being re-typed.

Pool, air conditioning, cleaning, repairs — scheduled around checkouts.

Clinics & practices

Scheduling, intake forms and follow-ups that run themselves.

Local practices with the same booking and reminder problem, minus the suitcases.

Tour and activity operators, transport and shuttle services, event and venue businesses — same shape, same fixes. If a calendar, a contract and a payment have to agree, this is the work.

How it works, and what it costs

Nothing is switched on in the middle of a busy week without you saying so, and nothing is built before the price is agreed.

1

We follow one booking

A free 30-minute call. You show us a reservation from enquiry to checkout, click by click, and we write down every place a person retypes something.

2

A written plan and a fixed price

Back within two business days: what connects, what cannot connect and will still need a person, the hours it saves, and the number.

3

Built and tested on copies

Your live reservations are never the test data. You watch it work on a copy of your season before it touches a real guest.

4

A supervised week, then handover

It runs on real bookings while we check every result and handle the exceptions. Then training, written notes, and the accounts stay in your name.

One process

Deposits, confirmations, contracts

from $690

Running from $149/mo, optional.

Booking hub

Units, bookings, contracts, guests

from $2,900

Plus $190/mo to run it.

Guest assistant

Answers in English or French

from $590

Plus $39/mo to keep it running.

Bilingual website

Custom built, not themed

from $1,200

Live in 24 hours, the clock starting the moment we have your content and you have approved the layout.

Starting prices, published. Channel, payment and property software stays subscribed in your name at your own rate — we do not mark it up and we do not resell it.

You can watch it being built

Your project runs through a client portal. Every update the team makes appears there as it happens, so you never have to email to ask whether anything moved this week — which matters when you are running a property in one hand and a phone in the other.

Updates as they happen

Posted when the work is done, not saved up for a status meeting.

Changes on request

Ask for something different at any point in the project. It gets answered in the portal, in writing.

Two named people

Cyrus and Tristan. Whoever replies is whoever is building it.

See the portal — the same system our clients use.

On site in Kissimmee

We are based in Orlando and travel across Central Florida for anything physical: the office network, the phone system at a rental counter, workstations, cabling, servers. If it has to be touched, we come and touch it — Kissimmee is a normal drive, not a call-out you have to justify.

And remote, anywhere in the US

The software side is built remotely, which means we work just as easily with an owner in another state, another time zone, or another country who happens to have units here. Plenty of this industry is run at a distance already; the system should not care where you are standing.

Kissimmee is one stop on the Central Florida service area. If your units or your office sit further north, there are pages for Orlando and Winter Garden too.

Straight answers

We take bookings from more than one listing channel. Can you keep availability straight?

That is the hardest part of this job, and the honest answer is that it depends on the channel: some give software a proper way to read and write availability, and some do not. We check every channel you use before we quote, and we tell you which ones can be kept in sync automatically and which ones will still need a person. What we will not do is promise a connection and discover afterwards that it does not exist.

Do you really work in French, or is that a line on a website?

Both founders speak English and French. That means a real conversation on the phone in either language, a site and booking flow that can run in both, confirmations and contracts written in both, and an assistant that answers a guest in the language they wrote in. In a town that hosts visitors from everywhere and where plenty of rental owners are not native English speakers, that turns out to matter more than any feature list.

We are heading into a busy stretch. Can you build without breaking what we run now?

Yes, and this is where we are careful. We build and test against copies of your data, never your live bookings, and you see it working before anything is switched on. Then it runs alongside your current process for a week while we watch every result and handle the exceptions a booking business always has — the late cancellation, the guest who extends, the unit that comes out of service. Nothing goes live in the middle of your season without you saying so.

What does a booking and rental system cost?

A single automated process — deposits, confirmations, a contract that chases its own signature — starts at $690. A full business hub, where units or vehicles, bookings, contracts and guests live on one screen, starts at $2,900, and running it costs $190 a month. Those are starting prices; the figure for your business is scoped and written down before anyone builds anything.

Do you come out to the property, or is it all remote?

Both, depending on what it is. Anything physical happens on site — the office network, the phones at the rental counter, workstations, cabling — and Kissimmee is a normal drive for us from Orlando. Software work is remote, because there is nothing to install in a room. We also work remotely with owners and managers anywhere in the US, including people who own units here and live somewhere else entirely.

Walk us through one booking

Thirty minutes, free. Show us how a reservation goes from enquiry to checkout today and we will come back with a written plan, the hours it saves and a fixed price. En anglais ou en français.

Kissimmee and Central Florida on site · remote across the US · support@cyrusmanagementgroup.com · Built by Cyrus and Tristan