MaintainSTR
The Property Care Operating System for Short-Term Rentals

Exceptional Guest Experiences Begin with Exceptional Property Care.

MaintainSTR is the Property Care Operating System built for short-term rental property managers. It helps property managers and contractors work together to care for every property, simplify day-to-day operations, and create exceptional guest experiences.

Built by a Property Manager
Built for Short-Term Rentals
30-Day Free Trial
White-Glove Onboarding
Designed by a property manager who believed there had to be a better way. MaintainSTR was built to reduce the chaos of Property Care so property managers, contractors, and guests could have a better experience.
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.

Why We Exist

There had to be a better way.

Every guest deserves an exceptional experience.

But exceptional guest experiences don't happen by accident.

They begin long before check-in — with a property that is cared for, guest-ready, and consistently maintained.

After spending more than six years operating short-term rentals, I discovered a simple truth:

Exceptional Guest Experiences Begin with Exceptional Property Care.

But delivering that level of care consistently wasn't easy.

The information needed to care for a property — photos, inventory, invoices, notes, conversations, and work history — was scattered across different people, devices, and systems. Small problems became costly surprises, and every day felt like putting out fires.

There had to be a better way.

That's why MaintainSTR exists — to help me and my fellow property managers work together with contractors to deliver exceptional Property Care and create better experiences for everyone involved.

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.

A True Story

“The bed desperately needs a new mattress — huge lumps and dips. We noticed it last year. It's gotten worse.”

— A returning guest

Same guest. Same issue. One year later.

That review wasn't just about a mattress. It was about what happens when a property's care history is fragmented: known issues become forgotten issues, and eventually the next guest finds them first.

Every property deserves a complete history of the care it has received.

The Reality

Property Care Shouldn't Feel Like Firefighting.

Managing short-term rentals means juggling hundreds of moving pieces every day.

  • • Guests are checking in.
  • • Contractors are on-site.
  • • Supplies need to be restocked.
  • • Inspections need to happen.
  • • Issues need to be resolved before they become guest complaints.

Most days don't go according to plan.

Instead of confidently managing their properties, property managers spend their day reacting to whatever problem demands attention next.

One forgotten task becomes an emergency.
One missing photo leads to another phone call.
One overlooked issue turns into a negative guest review.

Property Care shouldn't feel like firefighting.

It should be organized, proactive, and give you confidence that every property is receiving the care it deserves.

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, every contractor has the information they need, and every property manager has confidence that nothing important falls through the cracks.

That's why we built MaintainSTR.

MaintainSTR property detail view showing Smoky Mountain Escape with occupied status and open work orders

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

Meet MaintainSTR

One source of truth for every property.

MaintainSTR is the Property Care Operating System built for short-term rentals.

It brings together the people, information, and history needed to care for every property — all in one place.

Instead of chasing text messages, searching through photos, digging through invoices, or relying on memory, everyone works from the same source of truth.

Property managers
gain confidence.
Contractors
have the information they need to do great work.
Every property
receives the consistent care it deserves.

Because when Property Care works better, everything else gets easier.

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.

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

Track, prioritize, and resolve issues before they become guest problems.

Property History

Keep a complete history of every inspection, repair, photo, invoice, and conversation for every property.

Inventory Management

Know what every property needs before missing or damaged inventory impacts a stay.

Evidence-Based Work Completion

Verify completed work with photos and documentation so you always know what was done.

Contractor Payments

Approve invoices and pay contractors quickly without chasing paperwork.

And More…

MaintainSTR evolves with the real-world needs of property managers and contractors.

Inventory Management

Know every appliance in every property — down to the model and serial number.

Track consumables, appliances, and equipment for each property. Capture make, model, serial number, vendor, warranty, and condition so nothing is a guess when something breaks or needs replacing.

MaintainSTR inventory list with an expanded appliance record showing manufacturer, model, serial number, vendor, and warranty details
MaintainSTR iPhone app showing a property list with per-property Add Issue buttons

Built for the Field

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

Property managers 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 exceptional Property Care depends on all three.

Shridhar Sundaram (Shri)

Shridhar Sundaram (Shri)

Founder • Technology Executive • Owner, Bear Crest Cabins

Shridhar combines decades of software engineering and technology leadership with more than six 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 in delivering exceptional guest experiences.

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

Joshua O'Brien

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 it easier to care for properties and create better experiences for everyone involved.

In Their Words

From the people who use it every day.

Melinda
Short-Term Rental Property Manager
Joshua
Contractor, Lodge Masters LLC

Early Partner Pricing

We're currently welcoming a limited number of early Property Management partners.

Pilot pricing for early partners · 30-day free trial · Month-to-month · No long-term contracts · White-glove onboarding included

Every property portfolio is different. Book a personalized demo and we'll walk you through pricing for your portfolio, answer your questions, and help determine whether MaintainSTR is the right fit for your operation.

Every Property Deserves Exceptional Care.

If you believe exceptional guest experiences begin with exceptional Property Care, we'd love to show you how MaintainSTR can help your team.

30-Day Free Trial
Month-to-Month
White-Glove Onboarding
Personalized Setup
No Long-Term Contracts