HOA threatening $500/day fines for my Airbnb - CCRs from 2008 don't mention short-term rentals

I publish illustrative scenarios prepared by my practice. All participants and conversations are fictional. The fictional posts are not posts by real users, accounts of client experiences, or reports of actual results.
Illustrative scenario prepared by my practice.
TL;DR - Key Takeaways from This Thread

HOA STR Enforcement Basics

  • HOAs need explicit language in CC&Rs to ban STRs - vague "residential use" clauses are often insufficient
  • Board resolutions alone typically cannot create new rental restrictions - requires formal CC&R amendment
  • Florida Statute 718.110(13) protects rental rights for condo owners who purchased before restrictions

Grandfathering & CC&R Interpretation

  • Owners actively renting BEFORE a new restriction is adopted are usually grandfathered in
  • If you bought before the STR ban but weren't renting yet, protection is weaker
  • Check for "commercial use," "transient occupancy," or minimum lease terms in original docs

Hearing & Documentation Tips

  • ALWAYS request a hearing before fines are finalized - you have a right to be heard
  • Document everything: listing history, guest reviews, communications, fine notices
  • Excessive fines ($500/day) are often reduced or struck down as punitive
  • Check if HOA followed proper notice procedures for rule changes

When to Give Up vs. Fight

  • If CC&Rs explicitly prohibited STRs when you bought - you'll likely lose
  • If legal fees exceed potential rental income - consider settling
  • If HOA offers reasonable settlement (waive fines, stop hosting) - may be best outcome
  • If you have strong grandfathering claim - fight it, most HOAs back down
For informational purposes only. HOA law varies by state and specific governing documents.
Hypothetical question

I own a condo in a Miami building and have been running it as an Airbnb for the past 2 years. Made good money, never had any complaints from neighbors, guests have been respectful.

Now the HOA sent me a letter saying I'm in violation of the CCRs and owe $500/day in fines retroactive to when I started. They claim I owe $365,000.

Here's the thing - I read the CCRs from cover to cover before I started hosting. There's NOTHING in there about short-term rentals or a minimum lease term. The CCRs are from 2008, way before Airbnb was even a thing.

Can they really fine me for something that's not written in the rules?