Accounting Administrator

Company Overview

Casago First Coast is a vacation rental property management company operating across multiple Florida markets and part of the growing Casago franchise network. We are focused on delivering exceptional experiences for both homeowners and guests through a combination of responsive local service, operational excellence, and a strong commitment to accountability. As a fast-growing company, we take our financial, operational, and regulatory responsibilities seriously.

Our team values professionalism, accuracy, collaboration, and doing things the right way. We move quickly, support one another, and are committed to building long-term trust with our homeowners, guests, and team members alike.

We are building an in-house finance and compliance function. This role owns two things: the day-to-day financial operations of the business and the regulatory compliance lifecycle for our properties across multiple Florida jurisdictions. This is not a back-office support role. You will be working directly in our systems, managing both the numbers and the permits. You will also be tracking licenses, managing renewals, and making sure we are never caught off-guard by a regulation change or a missed filing deadline.

The right person has direct short-term rental or vacation rental experience, understands trust accounting, and brings the organizational discipline to manage a high volume of ongoing tasks without losing detail.

• Day-to-day bookkeeping: revenue recognition, journal entries, accruals, and month-end close
• Trust accounting within our PMS: reconcile owner accounts against collected revenue
• Bank reconciliations and clearance of undeposited funds
• Owner statement generation, review, and final release on a monthly cycle
• Month-end trust report reconciliation to verify system health

• Own the AP function using  integrated with Quick Books Online
• Vendor setup, W-9 collection, invoice coding, and payment scheduling
• Housekeeping vendor payments processed weekly
• All other vendor invoices handled as needed based on invoicing
• 1099 processing for owners and contractors annually

• Monthly lodging and occupancy tax calculations across multiple Florida jurisdictions
• Account for channel-remitted taxes and ensure non-remitted bookings are captured
• Prepare tax work papers and support timely filings
• Maintain a compliance calendar and proactively flag upcoming deadlines and changes

• Apply for and track city/county business licenses and STR permits across all active markets
• Research, document, and maintain a living database of local STR regulations by jurisdiction
• Manage renewal and relicensing timelines so no permit lapses without advance notice
• Coordinate with market-level team members on property-specific compliance needs
• Flag regulatory changes and required actions to leadership proactively
• Support new property onboarding by identifying and executing applicable permit requirements

• Monthly financial statements and KPI reporting
• Market-level analysis to support operational decisions
• Support annual budgeting and quarterly updates

• Direct experience in short-term rental or vacation rental property management at a portfolio of 500+ units
• Hands‑on experience with Streamline PMS (required; not just familiarity)
• 3+ years in bookkeeping, accounting, or a combined accounting/compliance role
• Working knowledge of trust accounting in a property management context
• Experience with AP end‑to‑end, including W‑9s and 1099 processing
• Familiarity with STR revenue flows: OTA remittances, channel taxes, owner disbursements
• Strong organizational skills and ability to manage a high volume of concurrent tasks
• Clear written communication for working with municipalities, vendors, and internal teams

• Paid time off such as PTO, sick days, and vacation days
• Health insurance
• Life insurance
• Dental insurance
• Vision insurance
• Retirement benefits or accounts