Appfolio Bookkeeping Jobs in Boca Raton, FL (NOW HIRING)

StaySouth is a fast-growing, locally operated vacation rental management company based in Southeast Florida, managing properties across Miami, Miami Beach, Fort Lauderdale, and Palm Beach. Founded by Ricardo Remak, who spent more than 10 years in senior operations roles supporting reservations, guest communications, and client management across 20,000+ property bookings in the U.S. and U.K. That depth of operational experience, at scale, across markets, is the foundation StaySouth is built on.

We are part of the Casago franchise network, one of the largest vacation rental management platforms in North America, with 40,000+ homes. That means our owners and guests benefit from national-grade technology and distribution, while working directly with a local team that actually lives here and cares.

We are now building out our core team as we grow, and this role is a key part of that infrastructure.

Compensation: $75,000 - $85,000

This is not a basic bookkeeping position. The Property Accountant will own the financial operations side of the business; managing trust accounting, OTA reconciliations, owner distributions, and reporting, and play a direct role in building the systems that let us scale cleanly.

You will work closely with the founder and have visibility into the full financial picture of the company. The right person is organized, proactive, and takes ownership without waiting for direction.

What You'll Do

Owner Accounting

• Prepare and distribute accurate monthly owner statements
• Manage owner distributions, reserve balances, and expense tracking
• Respond to owner accounting questions clearly and promptly

Trust Accounting & Reconciliation

• Maintain accurate trust and operating account records
• Perform daily, weekly, and monthly bank reconciliations
• Reconcile OTA payouts from Airbnb, Vrbo, and Booking.com
• Identify and resolve discrepancies quickly

Accounts Payable & Receivable

• Process vendor payments, contractor invoices, and refunds
• Track guest payments and outstanding balances
• Manage payment issues and coordinate vendor payment schedules

Financial Reporting & Systems

• Prepare monthly P&L reports, cash flow summaries, and operational reports
• Support forecasting, budgeting, and financial controls
• Help build and improve accounting workflows and automation as we scale

Requirements

What We're Looking For (Required)

• 3+ years of accounting experience in property management or hospitality
• Hands-on trust accounting experience
• Proficiency in QuickBooks Online
• Strong reconciliation skills: bank accounts, OTA payouts, merchant processors
• Advanced Excel or Google Sheets skills
• Exceptional attention to detail and ability to manage high-volume transactions
• Clear, professional written and verbal communication

Nice to Have

• Short-term vacation rental (STR) industry experience
• Experience with Guesty, Hostaway, Escapia, or AppFolio
• Familiarity with OTA payout reconciliation workflows
• Understanding of occupancy and lodging tax compliance in Florida

Benefits

After a 90-day probationary period, full benefits become available:

• Health, dental, and vision benefits

• Paid time off and paid holidays
• Performance-based bonus opportunities
• Flexible/hybrid work environment
• Growth opportunity; this role is foundational as we scale