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For property managers & vacation rental operators

You already have the software. We build the part that's missing.

You've got your tools already, your booking software, a pricing app, a cleaning app, accounting. The problem isn't more software. It's that they don't talk to each other, they're missing features you need, and there are things they could do that nobody ever told you were possible. We build that missing layer on top of what you run, and we run our own vacation rentals on it first.

Fixed price, quoted up front Every project is quoted exactly, and fixed, after a free Payback Map.

Field AssistYour playbook, on their phone
What's the gate code at Palm Cove 12?
Gate code: 4417. Lockbox is on the left post, code 2290.From your property playbook
Pool heater won't turn on
Breaker panel by the pump, flip Pool Heat, then hold SET for 3 seconds. Give it ~40 min.From your property playbook
Ask anything about a property...

Where it pays off first

Three things your current tools don't do, and should.

Most managers already have software. These are the gaps we see cost the most, and close the fastest. Your free Payback Map sizes the exact return for your operation.

Deeper integration between the tools you already have

Your booking software, pricing tool, cleaning app, and accounting don't talk, so you're the glue, copy-pasting and double-checking. We connect them so data moves on its own and the gaps between them get filled. No rip-and-replace.

You get back: the hours you lose being the middleman between systems, and far fewer things slipping between them.

Guest and tenant issues captured and dispatched on their own

A guest or tenant reports a broken AC at 11pm. Instead of it sitting in an inbox until morning, we catch it the second it lands, log it against the property, and send it to the right person automatically, with the details they need to fix it.

You get back: problems handled before they become bad reviews, and nothing lost in an inbox overnight.

A mobile knowledgebase and chatbot for your field team

Your techs and cleaners stop keeping notebooks and calling the office. They ask their phone, gate code, how to reset the heater, where the water shutoff is, and get the answer instantly. It only answers from your own playbook, so it's grounded in your real details, not guesswork.

You get back: a field team that's faster and self-sufficient, and an office that stops fielding the same questions.

Not the basic version

We don't just do what your software does. We take it further.

Anyone can list features. The difference is what we bolt onto each one, in time saved, cost cut, or revenue you were quietly leaving behind.

Owner statements, generated automatically
+the matching invoices go out on their own, so you get paid without lifting a finger.
Dynamic pricing matched across every channel
+with regular accuracy checks, so a stale rate never quietly costs you revenue.
Review requests after every stay
+turned into automatic social posts and marketing that win your next booking.
Turnover and cleaning crew scheduling
+with route optimization that cuts drive time, fuel, and payroll for the whole crew.
Maintenance requests captured
+auto-dispatched to the right person the moment they land, so nothing sits waiting.
Bookings, accounting and ops in one view
+the money slipping between your systems gets caught before it's gone for good.
Unbilled work, found and flagged
+revenue you're leaving on the table today, recovered automatically.
Listing photos enhanced automatically
+every listing looks pro without a photographer, and books better for it.
Your whole operation on one screen
+an alert the second something breaks, so you fix it before a guest ever notices.
Owner portal with live statements
+owners self-serve their numbers, so you stop losing hours to "where's my money" calls.
A nightly self-check for anything dropped
+a missed turnover never becomes a guest walking into a dirty unit and a one-star review.
A morning summary sent to your phone
+the whole operation's health before your first coffee, without logging into anything.

Don't see the one eating your week? If you can describe the busywork, we can probably build it. Free Payback Map →

Common questions

Property managers ask us this first.

I already use Guesty, Hostaway, or Breezeway. Do I have to switch? +

No. We build on top of the tools you already run, there is no rip-and-replace. We connect them, fill the gaps they leave, and add the features they never did.

I already have software for most of this. What can you actually add? +

Three things. Deeper integration so your tools finally talk to each other and stop making you the glue. The features you need that your current software never added. And the things it could do that nobody ever told you were possible, like automatic guest-issue dispatch, or a chatbot your field team asks instead of calling the office.

Do you actually run a property management operation? +

Yes. We run our own vacation rental operation on the same automation we build for clients. It gets tested in the field on real guests, real owners, and real turnovers before it ever reaches you.

How much does it cost? +

Every build is quoted exactly, and fixed, after a free Payback Map. The number you're given is the number you pay, and you know what you're getting back before you commit. We start with one focused build rather than a rebuild, so the first step stays small.

How long until it's running? +

A focused first build is usually live in weeks, not months. We design it, build it, test it against your real workflow, and hand it back running with guardrails so you can trust it from day one.

Free, no obligation

Let's find your fastest ROI.

A free 30-minute Payback Map. We'll pinpoint the one or two places automation would pay off fastest across your doors, with the numbers, before you build anything.

Last updated August 18, 2026  ·  Written by Justin, founder of Taskwell360