The Property Care Operating System for Short-Term Rentals

Exceptional Guest Experiences Begin withExceptional Property Care.

Every issue — broken, missing, or worn — is captured, tracked, fixed, and documented in one place, so nothing you know about slips.

Built by a Property Manager

Built for Short-Term Rentals

30-Day Free Trial

Things will break, get missed, or go missing. That's not the failure. The failure is knowing about it and letting it slip — spoiling a guest's vacation, interrupting your evening, and hurting your business. I built MaintainSTR so that never happens on my properties again.
— Shri, Founder, MaintainSTR · Owner, Bear Crest Cabins

MaintainSTR property manager dashboard showing open invoices, pending quotes, and pending change requests

Everything that needs your attention, in one place — the moment a property manager logs in.

A True Story

The hot tub wasn't the problem.

On the guest's arrival morning, my cleaner reported a hot tub issue.

The message was buried in my inbox.

Later that evening, the guest discovered the same problem.

My technician couldn't get there until two days later, so I ended up with an upset guest, a partial refund, and still had to pay for the repair.

The problem wasn't the hot tub.

Nothing was broken that couldn't be fixed. The failure was that a known problem slipped.

Why We Exist

A hundred small things.

Think about the best trip your family ever took. You probably can't point to one thing that made it great. That's because nothing went wrong. The hot tub was hot, the coffee pot worked, the hair dryer was in the drawer, the grill was clean.

Things will break, get missed, or go missing — that's just running properties. The real failure is knowing about a problem and letting it slip. It costs you a guest's weekend, your evening, and your bottom line.

After seven years operating short-term rentals, I learned that the difference between a great stay and a bad review is rarely a big thing. It's whether the small things were caught.

That's why MaintainSTR exists — so property managers and the contractors they rely on never let a known problem slip.

One of the founder's short-term rental cabins in the Smoky Mountains — One of the founder's own cabins — Bear Crest Cabins runs on MaintainSTR every day.

How We Do It

Five ways nothing slips.

A system that won't let you drop the ball

Every known issue, big or small, is captured, owned, and followed to done — across the property manager and the contractor as partners.

Proactive care

Recurring inspections, preventive maintenance, and inventory checks that find the small things before a guest does.

A transparent record of every property, shared by both sides

Every property has a Primary Contractor who carries its full history — what's been fixed, what keeps coming back, what's still open. Shared with the property manager, so both sides see the same record.

Fair, fast money

Clear quotes, quick invoicing, and on-time payment, so good contractors keep showing up and the work keeps flowing.

A scoreboard

Problems a guest had to report versus problems your team caught first, trending down month over month.

MaintainSTR work order detail with progress pipeline, issue documentation across Discovery, Assessment, and Resolution phases, repair photos and video, and live chat

Every repair documented with photos and video, from first report to final sign-off.

The Relationship

Your property deserves a primary care doctor.

Think about a child. When something's wrong, you don't forget it. You don't file it away and hope it resolves. You find a solution, and you remember it — the allergy, the ear infections, the thing that always flares up in winter. That's what a primary care doctor is for: someone who knows the whole history, not just today's symptom.

A property deserves the same. It's just harder. A child has a handful of recurring issues a few times a year, and grows out of them. A property has three or more every month, and gets more demanding as it ages — never less.

That's why MaintainSTR is built around a Primary Contractor: one relationship that carries the property's whole history. Every issue, every fix, every inspection, every thing that keeps coming back. Not whoever was available that Tuesday.

The more you treat a property like something you love, the better it gets treated — and the better your guests' stay.

The Positioning

Property Care Deserves Its Own Operating System.

Reservations, pricing, and guest communication help fill your calendar.

But they don't care for your properties.

Property Care is its own operation — with its own workflows, history, contractors, inventory, inspections, and responsibilities.

Yet most property managers are forced to manage it through disconnected tools, spreadsheets, text messages, and memory.

Property Care deserves more.

It deserves its own Operating System.

One place where every property has a complete history, a Primary Contractor who knows it, and every technician has the information they need, and every property manager has confidence that nothing important falls through the cracks.

That's why we built MaintainSTR.

Every property, organized: status, owner, contractor, and every open work order in one view.

One Operating System

Every part of Property Care, in one place.

Property Care isn't one task. It's hundreds of decisions, inspections, repairs, inventory, contractor coordination, documentation, invoices, and property history — all working together to keep every property guest-ready.

MaintainSTR brings every part of Property Care together into one connected Operating System, giving property managers and contractors a single place to manage the care of every property with confidence.

Issue Management

Issues are captured and triaged as issues first — fix it, defer it, or escalate it. They only become work orders once someone decides they should.

Property History

The complete record of a property — every inspection, repair, photo, and conversation — held by the Primary Contractor who knows it best, so history doesn't reset when people change.

Inventory Management

Track everything in a property — appliances and equipment, plus the consumables and furnishings a guest notices: air filters, spare batteries, hair dryers, quilts, linens. Know what's missing or worn before it affects a stay.

Evidence-Based Work Completion

Every photo and video is stamped with location and time at capture — even with no signal — so proof of work is proof.

Contractor Payments

Approve invoices and pay contractors quickly without chasing paperwork.

Quotes & Approvals

Quotes come to you before work starts. Set a threshold per contractor and anything under it approves itself — nobody waits on you.

Inspections & Preventive Care

Recurring inspections and preventive schedules that find small things before a guest does.

Equipment Health

HVAC that reports it's running but isn't cooling looks fine on a thermostat and terrible to a guest. MaintainSTR watches the equipment's actual behaviour and flags a unit that's stopped doing its job — then confirms the repair actually held.

Several of these mechanisms are patent-pending.

Inventory Management

Know everything in every property — equipment down to the model and serial number, and the everyday items a guest actually notices.

Appliances and equipment are captured with make, model, serial number, vendor, warranty, and condition, so nothing is a guess when something breaks or needs replacing. The same record covers the consumables and furnishings that make a stay feel cared for — air filters, spare batteries, hair dryers, quilts, and linens — so you know what's missing or worn before a guest does.

MaintainSTR inventory list with an expanded appliance record showing manufacturer, model, serial number, vendor, and warranty details

Built for the Field

Log an issue from anywhere — right from your phone, on-site.

Property managers, in-house technicians, and contractors capture issues, photos, and updates the moment they see them. No forgotten sticky notes, no lost text threads — it all lands in the same operating system.

Ready to see it on your properties?

Meet the Team

Meet the Team Behind MaintainSTR.

MaintainSTR was built through the combined experience of technology, property management, and Property Care — because a great stay depends on all three.

Shridhar Sundaram (Shri)

Founder • Technology Executive • Owner, Bear Crest Cabins

Shridhar combines decades of software engineering and technology leadership with seven years of operating short-term rentals. Drawing on both experiences, he built MaintainSTR to simplify Property Care, reduce operational chaos, and make it easier for property managers and contractors to work together so nothing they know about slips.

His work on the platform has produced patent-pending innovations at its core, with additional filings planned as MaintainSTR evolves.

Joshua O'Brien

Founding Head of Contractor Operations • Owner, Lodge Masters LLC

Joshua owns and operates Lodge Masters LLC, a Property Care company serving short-term rental properties. MaintainSTR powers the day-to-day operations of his business — from recurring property inspections and issue management to evidence-based work completion and contractor workflows.

Joshua continues to shape MaintainSTR from the field, ensuring the operating system works as well for contractors as it does for property managers.

Together

Every improvement to MaintainSTR is guided by real-world experience — not assumptions. It continues to evolve through the combined perspectives of technology, property management, and Property Care operations, with one shared goal:

Make sure nothing you know about ever slips.