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.
Bookkeeping & Trust Accounting
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
Accounts Payable
Own the AP function using Bill.com integrated with QuickBooks 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
Tax Compliance
Monthly lodging and occupancy tax calculations across multiple Florida jurisdictions
Account for channel-remitted taxes and ensure non-remitted bookings are captured
Prepare tax workpapers and support timely filings
Maintain a compliance calendar and proactively flag upcoming deadlines and changes
Regulatory Compliance & Permitting
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
Financial Reporting
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
Bookkeeping & Trust Accounting
• 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
Accounts Payable
• Own the AP function using Bill.com integrated with QuickBooks 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
Tax Compliance
• Monthly lodging and occupancy tax calculations across multiple Florida jurisdictions
• Account for channel-remitted taxes and ensure non-remitted bookings are captured
• Prepare tax workpapers and support timely filings
• Maintain a compliance calendar and proactively flag upcoming deadlines and changes
Regulatory Compliance & Permitting
• 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
Financial Reporting
• 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
• Florida-specific STR experience, particularly in Northeast Florida markets
• Experience with multi-jurisdiction lodging and occupancy tax compliance
• Prior experience in a franchise or multi-entity property management environment
• Experience with permitting, planning, or zoning processes
• CPA, CMA, or paralegal designation, or actively pursuing