Short-Term Rental Operations, Bookkeeping & Personal Assistant

Position: Long-Term
Hours: 20–40 hours per week
Compensation: $4 USD per hour
Schedule: Required availability between 8:00 AM and 8:00 PM EST daily. Specific working hours will fall within this coverage window.
About the Role
We are looking for a highly organized, proactive Virtual Assistant to help manage the daily operations and bookkeeping of multiple U.S.-based Airbnb and short-term rental properties. The role will also include personal, administrative, purchasing, and travel-related responsibilities.
This role is ideal for someone who can take an unstructured request, research the situation, present good options, and follow the selected solution through to completion.
We do not want someone who only reports problems or waits for step-by-step instructions. We want someone who takes ownership, follows up without being reminded, verifies that work was actually completed, and knows when an issue needs to be escalated.
This is a long-term position with the potential for additional responsibility as our real estate portfolio grows.
Bookkeeping and Financial Administration
Bookkeeping will be a major part of this position. You will help keep the finances for each property and business entity accurate and organized.
Responsibilities include:
Manage bookkeeping using Intuit QuickBooks Online.
Review and classify bank and credit-card transactions regularly.
Ensure every transaction is assigned to the correct property, business entity, account, and expense category.
Separate expenses across multiple short-term rental properties and LLCs.
Reconcile bank accounts and credit-card accounts.
Match receipts and invoices to their corresponding transactions.
Track cleaner payments, contractor invoices, property supplies, repairs, utilities, subscriptions, and other operating expenses.
Identify duplicate, missing, unusual, or incorrectly categorized transactions.
Ask for clarification rather than guessing when the correct classification is uncertain.
Maintain organized digital copies of receipts, invoices, statements, and supporting documents.
Track reimbursements, refunds, credits, security deposits, and vendor payments.
Prepare monthly property-level income and expense summaries.
Help maintain accurate profit-and-loss reporting for each property.
Coordinate with our accountant or tax professional when information or documentation is requested.
Maintain a list of recurring payments and flag unexpected price increases or duplicate subscriptions.
Direct experience with QuickBooks Online and property-level bookkeeping is preferred.
Cleaning and Turnover Coordination
Monitor reservation and turnover calendars.
Schedule cleaners after guest checkouts.
Confirm that every turnover has an assigned cleaner.
Communicate early check-ins, late checkouts, guest counts, and special instructions to cleaners.
Confirm that cleaners arrived and completed each turnover on time.
Coordinate backup cleaners when someone becomes unavailable.
Follow up on cleaning problems until they are resolved.
Maintain cleaning checklists, schedules, invoices, and payment records.
Maintenance and Vendor Coordination
Coordinate lawn mowing, pool or hot-tub service, pest control, repairs, and other recurring property services.
Contact cleaners, contractors, handymen, technicians, and local vendors by phone, text, or email .
Obtain and compare estimates when appropriate.
Schedule approved work and coordinate property access.
Follow up until the work is actually completed.
Request photos, invoices, or other proof of completion.
Maintain records of maintenance issues, costs, warranties, and vendor contact information.
Identify reliable backup vendors before emergencies occur.
Guest and Reservation Support
Monitor Airbnb, Booking.com, VRBO, Hospitable, or related platforms as assigned.
Answer routine guest questions clearly and professionally.
Coordinate solutions for lockouts, missing supplies, cleanliness problems, amenity issues, and maintenance requests.
Escalate safety issues, refund requests, major repairs, unhappy guests, or unusual situations promptly.
Assist with reservation changes, guest reviews, and Airbnb support cases when needed.
Gather photos, messages, receipts, and other documentation for damage or reimbursement claims.
Property Administration
Track recurring services, permits, licenses, utilities, insurance, subscriptions, and renewal dates.
Monitor property supplies and coordinate approved restocking.
Keep listing information, amenities, house rules, and property guides accurate.
Organize property documents and operational records.
Create and improve SOPs and checklists for recurring tasks.
Provide a concise weekly report covering open issues, completed work, upcoming turnovers, expenses, and decisions needed.
Personal and Travel Assistance
The position will also include non-property tasks such as:
Research and compare flights based on total price, duration, stops, baggage rules, airports, and cancellation policies.
Research hotels, Airbnbs, transportation, restaurants, activities, and other travel details.
Create organized itineraries containing reservation details, addresses, confirmation numbers, travel times, and important deadlines.
Verify important details directly instead of relying only on search-result summaries or AI-generated information.
Book approved flights, accommodations, transportation, reservations, and activities.
Monitor travel plans for schedule changes, cancellations, or missing details.
Research products, services, vendors, subscriptions, and personal purchases.
Start, change, renew, or cancel subscriptions after receiving approval.
Place approved online orders and track deliveries, returns, credits, and refunds.
Make phone calls and follow up with companies on our behalf.
Organize calendars, reminders, documents, and recurring personal tasks.
Assist with basic video editing as needed, including trimming clips, adding captions and music, and formatting videos for social media. Prior video-editing experience is a plus, but is not required to be hired.
Purchasing and Financial Boundaries
You may eventually receive access to authorized accounts or controlled payment methods. Trust and discretion are essential.
Significant purchases must be approved before payment.
Never change payment, payout, banking, tax, or account-ownership information without explicit approval.
Never send money to yourself or an unapproved person or vendor.
Record purchases and save receipts immediately.
Confirm cancellation and refund policies before booking.
If instructions appear unusual or potentially fraudulent, stop and verify with us directly.
Never share passwords, financial information, guest information, or property access codes with unauthorized parties.
Required Qualifications
Excellent spoken and written English.
Experience as a Virtual Assistant, bookkeeper, property-management assistant, or operations coordinator.
Previous Airbnb or short-term rental experience is strongly preferred.
Comfortable calling U.S. businesses, cleaners, contractors, and customer-support departments.
Strong online research and comparison skills.
Able to manage multiple deadlines and follow up without reminders.
Able to distinguish between an urgent issue and one that can wait.
Comfortable handling confidential personal, guest, property, and financial information.
Reliable computer, stable high-speed internet, and preferably backup internet.
Comfortable using spreadsheets, task-management software, messaging applications, and AI tools.
AI may be used to work efficiently, but all important information must be independently verified.
Able to maintain availability during the required 8:00 AM–8:00 PM EST coverage window.
Helpful Experience
Experience with any of the following is beneficial:
Intuit QuickBooks Online // Bookkeeping for multiple properties or LLCs
Airbnb, VRBO, or Booking.com experience
Hospitable, Guesty, Hostaway, or another property-management system
PriceLabs or other dynamic-pricing software
Vendor dispatch, hospitality, customer service, or property maintenance
Basic video editing using CapCut, Canva, Adobe Premiere Pro, or similar tools (nice to have, not required).
What Success Looks Like
Within the first 30–60 days:
Transactions are consistently classified under the correct property, entity, and expense category.
Accounts and receipts remain organized and ready for monthly review.
Unknown transactions are flagged promptly instead of being guessed.
Every turnover is properly assigned and confirmed.
Cleaners and vendors receive the correct information without needing to chase us.
Maintenance problems are tracked through completion.
Upcoming renewals, services, and property needs do not surprise us.
Travel research is accurate, concise, and ready for a decision.
Approved bookings and purchases are completed correctly.
You identify potential problems early and bring us recommended solutions.
We spend significantly less time following up on routine financial, operational, and personal tasks.
How to Apply
Please include:
A short introduction.
Whether you have managed bookkeeping for multiple properties, businesses, or LLCs and your experience.
Your relevant Airbnb or short-term rental experience along with any property-management tools you have used.
Your experience coordinating cleaners, contractors, or other field-service providers.
Confirmation that you can work 20–40 hours per week and maintain the required availability between 8:00 AM and 8:00 PM EST.
A link to a 1–2 minute Loom video introducing yourself and describing a scheduling, bookkeeping, or operational problem you solved.
The word “pineapple” in the subject line so we know you read the entire posting.
Please also answer the following scenario in no more than eight sentences:
A cleaner assigned to a same-day turnover says she cannot come. The current guest checks out at 11:00 AM, and the next guest checks in at 4:00 PM. Explain exactly what you would do.
Applications that do not answer the