100’s of Recurring Cleaning and Maintenance Tasks Organized in One System

The Situation

A vacation rental management firm running short-term cabin rentals came to us with a system that had outgrown itself. Each property needed its own tracking, its own scheduling, its own communication thread with owners and guests. The team also needed to coordinate cleaning crews, maintenance staff, and on-the-ground operators who all worked across multiple properties at the same time.

Their existing setup had been built piece by piece as the business grew. It worked when there were a few cabins. It stopped working as the portfolio expanded. Properties were scattered across different spaces. Permissions weren't clean, so cleaning crews could see things they didn't need to see, and miss things they did. Calendar visibility was fragmented. Comments and history from older setups risked getting lost as the team tried to reorganize.

They needed one workspace that could handle every property as its own unit, every role with its own appropriate view, and every recurring task (cleaning visits, maintenance checks, owner reports) properly scheduled and visible to the right people.

Our Approach

We built one ClickUp workspace designed around how the firm actually operates day to day.

Each property got its own list, with custom stages reflecting the lifecycle of a vacation rental from onboarding through active management. Tags were configured to auto-apply so the team didn't have to manually classify every task. We built multiple views for project management, calendar planning, and operational coordination, so the same data could be looked at differently depending on what the team needed in the moment.

For the operational side, we added a dedicated stage for scheduled cleaning visits. Cleaning crews work as guest users in the system, and they only see the cleaning tasks assigned to the specific properties they cover. No accidental access to owner conversations, financial details, or unrelated properties. Just what they need to do their job.

Dashboards were built to give leadership a single view across all properties, with permissions configured so internal team members, guest users, and external stakeholders each see what's relevant to them and nothing more.

Throughout the build, we worked iteratively with the team. A draft setup was reviewed, refined, and finalized based on how the team actually wanted to work, not how a generic template said they should.

Before

• Properties scattered across separate spaces with no unified structure

• Cleaning crews and maintenance staff had unclear visibility into their assigned tasks

• Calendar coordination across properties required manual cross-referencing

• Permissions weren't clean, leading to either too much access or not enough

• Comments, history, and notes risked being lost during reorganization

• The system worked for a few cabins but couldn't scale with the portfolio

After

• One ClickUp workspace with every property as its own structured list

• Custom stages reflecting the actual lifecycle of a vacation rental, from onboarding to active management

• Auto-applied tags so classification happens without manual work

• Multiple views for project management, calendar planning, and operational coordination

• A dedicated stage for scheduled cleaning visits, visible only to the cleaning crews assigned to those properties

• Dashboards giving leadership a single view across the full portfolio, with permissions configured by role

• Guest user access for cleaning crews and external collaborators, scoped to exactly what they need to see

The Outcome

The firm now runs every property, every role, and every recurring task in one connected workspace. Cleaning crews see their work. Maintenance sees theirs. Leadership sees the full portfolio. Owners and guests stay in the loop without getting access to anything they shouldn't.

What used to require manual coordination across scattered spaces now happens in one place, with clean permissions and the right view for every role. The workspace was built to scale with the portfolio, so as new cabins come on, the structure is ready for them.