Rental Property Accountant

About this role

About StaySouth
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
The Role
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