Vacation Rental Booking Tips

Vacation rentals are a great way to enjoy the Florida Keys—but like anywhere in the world, scams and unlicensed properties can be a risk. Taking a few precautions will help make sure your stay is safe, legal, and stress-free.

How scams work: In many cases, scammers post fake listings, copy real estate ads, or ask for unusual payments (like wire transfers or mailed checks). Sometimes they’ll even ask you to sign contracts for longer stays than you want, or pretend you’re a “friend” or “relative.” These are red flags.

Why it matters: Illegal rentals may not meet fire, safety, or building codes. They may also be skipping required inspections, proper trash removal, or taxes—all of which protect both visitors and the community. In the Keys, short-term rentals (less than 28 days) must also have a licensed local manager available 24/7.

Tips for Booking Legitimate Rentals

  • Check the license – All vacation rentals in the Keys must be licensed. Ask for a copy of the transient license before paying. Rentals of 28 days or less usually also require a local permit.
  • Look for signs – In Key West, Marathon, and Islamorada, licensed short-term rentals must post a medallion or license number on-site and in ads.
  • Pay smart – Use a major credit card. Most licensed rental firms accept them, and cards typically offer fraud protection.
  • Skip wire transfers – Never send money electronically to someone you haven’t met in person.
  • Verify the owner – Be cautious if someone claims to be out of the country or asks you to pay another person. Cross-check names, phone numbers, and addresses online.
  • Trust your instincts – Deep discounts or offers that feel “too good to be true” often are.
  • Check memberships – Legitimate agents are often members of local chambers of commerce or lodging associations.

If you suspect you’ve encountered a scam, you can contact the nearest Chamber of Commerce to file a complaint, which will be forwarded to the right agencies.

Florida Keys chambers of commerce phone numbers:

Key Largo: 1-800-822-1088/305-451-4747

Islamorada: 1-800-FAB-KEYS/305-664-4503

Marathon: 1-800-262-7284/305-743-5417

Lower Keys: 1-800-872-3722/305-872-2411

Key West: 1-800-LAST-KEY/305-294-2587 

How Do I Verify a Vacation Rental is Legitimate? 

For rentals of 28 days and less, you can contact the municipality in which it is located:

City of Key West: 
City Licensing Office , 305-809-3957, email cwalker@cityofkeywest-fl.gov

Unincorporated Monroe County: (Key Largo and the Islands of the Lower Keys; including Big Pine Key, Sugarloaf, Summerland, Stock Island, Little Torch Key, Geiger Key, Cudjoe Key, Saddlebunch Keys and Ramrod Key)
Monroe County Code Compliance, 305-289-2810 

Marathon: 
Marathon Code Compliance, 305-289-4108

Key Colony Beach: 
City of Key Colony Beach - 305-289-1212 

Layton: 
City of Layton Code Enforcement - 305-664-4667

Islamorada: 
Islamorada Code Compliance - 305-664-6435

Lower Keys or Key Largo -  file a complaint with Monroe County online

For monthly rentals, verify the property’s Monroe County Business Tax license for transient rental online, or call the Monroe County Tax Collector’s Office at 855-422-4540. 

If You Suspect a Scam

Report it to local law enforcement, the Monroe County Tax Collector and the U.S Federal Trade Commission (FTC), whose investigators frequently collaborate with local law enforcement officials. 

Monroe County Sheriff’s Office: 305-289-2351
City of Key West Police Department: 305-809-1111 (non-emergency line)
Monroe County Tax Collector: 1-855-422-4540 (toll-free) or mail@monroetaxcollector.com
Federal Trade Commission: toll-free 1-877-FTC-HELP (1-877-382-4357)