Bookkeeper — Short-Term Rental​/Property Management

About Topkey

Topkey is the leading financial automation platform built specifically for vacation rental managers. Integrating directly into your PMS and accounting software, Topkey provides a single, unified system that automates expenses, bookkeeping, receipts, banking*, corporate cards, AP/bill pay, and more.

Topkey partners with numerous vacation rental property managers to increase profitability by eliminating cash leakage and automating time-consuming financial workflows. As the only expense platform in the property management industry with direct integrations to Visa, American Express, and Mastercard, Topkey delivers unmatched accuracy, flexibility, and confidence over your expenses. See what our customers say about using Topkey /customers.

We’re backed by top-tier investors like Felicis Ventures, Andreessen Horowitz (a16z), and Y Combinator. Topkey is recognized as one of the top emerging vertical startups, and our trajectory is steep. We’re looking for driven individuals to join our team and help shape the future of financial infrastructure in the $110 billion hospitality market.

We’ve been featured in numerous media outlets, including Axios, Wall Street Journal, Fortune, Phocuswire, Short Term Rentalz, and Fintech Global.

We're looking for a bookkeeper with short-term rental or property management experience to join the team. You'll handle the day-to-day bookkeeping work that keeps property-level financials clean and accurate, and you'll get close to the accounting workflows we're continuously improving on the product side.

This is a strong fit for someone earlier in their career who knows their way around STR books, wants to sharpen their skills inside a growing fintech company, and is curious about how modern accounting tools are built.

• Categorize transactions, reconcile accounts, and keep the books current on a rolling basis
• Process accounts payable and receivable
• Assist with month-end close tasks, including reviewing ledgers and flagging anomalies
• Maintain owner ledgers and property-level records
• Help prepare owner statements and supporting reports
• Handle data entry, documentation, and file organization with care
• Flag recurring issues or friction points so we can address them at the workflow level
• Partner with senior accounting team members on cleanup and onboarding projects

• 1-3 years of bookkeeping experience, with exposure to short-term rental, vacation rental, or property management bookkeeping
• Comfortable in Quick Books Online
• Some exposure to a PMS (Guesty, Track, Hostaway, Streamline, Owner Rez, Rentvine, Hostfully, or similar) preferred
• Solid Excel skills
• Detail-oriented, organized, and responsive
• Willing to ask questions and learn on the fly
• Fluent English (B2+)
• Availability during U.S. business hours
• Works as an independent contractor

• Competitive pay based on experience
• Remote
• Paid time off
• Meaningful growth path alongside senior accountants and a technical team building the next generation of property management financial tools

In your application, include 2–3 sentences describing any STR or vacation rental bookkeeping you've done and which PMS platforms you've worked with. Applications without directly relevant experience will not be prioritized.

Topkey is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC.