Short-Term Rental Operations Manager & Bookkeeper (Long-Term Role)

Short-Term Rental Operations Manager & Bookkeeper (Long-Term Role)

We are seeking one highly reliable, detail-obsessed professional to fully own the operations, bookkeeping, and administrative systems for our short-term rental portfolio (Airbnb / VRBO).

This is not a task-based VA role.
This is an ownership-level position for someone who thrives on organization, systems, and running operations independently — without babysitting.

What You’ll Own

End-to-end Airbnb & VRBO operations

Guest communication (pre-arrival through post-checkout)

Vendor coordination (cleaners, maintenance, supplies)

Issue tracking, resolutions, and operational follow-ups

Bookkeeping (QuickBooks or similar)

Expense tracking

Reconciliations

Monthly financial reporting

Digital file management

Maintain a clean, logical Google Drive “online file cabinet”

Organize invoices, receipts, contracts, property documents, and SOPs

Create and enforce clear naming conventions and folder structures

Administrative systems

Build and follow checklists

Document workflows and SOPs

Keep records current, accurate, and audit-ready

Bonus (not required, but a plus):

Light social media support (posting pre-approved content)

Assist with basic property or brand updates as needed

No content creation required unless already skilled

Who We’re Looking For

Proven short-term rental experience (Airbnb/VRBO required)

Strong bookkeeping skills with high attention to detail

Exceptionally organized and systems-driven

Able to work independently with minimal oversight

Proactive problem-solver — you see issues and resolve them

Excellent written English

Comfortable with US Eastern Time overlap

Seeking a long-term, stable role

What We Offer

$7–$10/hour depending on experience

Long-term position with growth opportunities

Clear expectations and systems

Trust and autonomy — no micromanagement

Competitive pay for a high-caliber professional

Screening Question (Required)

You are given a Google Drive with 500+ unorganized files (invoices, receipts, contracts, and STR documents) and no existing structure.
Describe, step by step, how you would organize this into a clean, functional online filing system.
Please include:

Folder structure

Naming conventions

How you would prevent it from becoming disorganized again

Applications that do not answer this question in detail will not be considered.

Reply to this job post state Eastern hours 11-5 to verify you can work