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

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?

FINAL UPDATE - RESOLVED: Closing out this thread with the full resolution for anyone who finds it in the future.

Final outcome:

• $365,000 in fines -> $0 (completely waived)
• Grandfathered status confirmed in writing - I can continue hosting
• HOA paid half my legal fees ($1,250 reimbursed)
• Reasonable compromise - I register my unit and accept responsibility for guest conduct

What made the difference:

1. The HOA failed to follow their own procedures for rule changes
2. They exceeded their own bylaws' fine limits ($500/day vs $100/day max)
3. No notice of violation before the massive fine letter
4. Having an experienced condo attorney who knew Florida law

Advice for others facing HOA STR disputes:

• Get a Florida condo attorney IMMEDIATELY - $2,500 saved me $365k
• Check if the HOA followed proper procedures for rule changes
• Look for grandfathering protections under Florida Statute 718.110(13)
• Request all documentation - board minutes, fine schedules, amendment records
• Don't panic at big numbers - HOAs often bluff with inflated claims
• Get involved in HOA governance to prevent future issues

Thanks to everyone who contributed advice, especially @order_in_the_court_11 for the legal guidance. This community helped me fight back when I thought I was going to lose everything. Still hosting, still happy, and now on the HOA committee to make sure this doesn't happen to others.

Found this thread while researching for my own situation in suburban Chicago. Wanted to share a recent development. The Illinois Condominium Property Act (765 ILCS 605) was amended and now requires that any new rental restriction adopted by a condo board must be approved by at least 75% of unit owners at a properly noticed meeting.

My HOA board passed a blanket STR ban via board resolution in 2024 without a full owner vote. When I pointed out the new statutory requirement, they initially pushed back. I sent them a demand letter citing the specific statute and demanding they rescind the resolution or hold a proper vote. They backed down within two weeks.

The broader lesson is that state legislatures are increasingly stepping in to regulate the HOA-versus-STR battle. Florida, California, Illinois, and several other states have all passed or amended laws addressing this issue. Before you fight your HOA, check whether your state has recently updated its condominium or HOA statutes.

Also worth noting: even in states that give HOAs broad authority, procedural defenses remain powerful. Always request board minutes, notice documentation, and the fine schedule from the governing documents. Procedural errors are often easier to prove than substantive legal arguments about whether STRs qualify as residential use.