Thinking about buying a Florida Keys property for short-term rental income? The opportunity is real, but the rules change from island to island and even block to block. If you want predictable returns, you need a plan that fits local laws, taxes, and HOA rules from day one. In this guide, you’ll learn how the Keys’ vacation-rental rules work, how they differ from nearby Miami-Dade markets like Florida City, and exactly what to check before you write an offer. Let’s dive in.
Keys vs. Miami-Dade: different rulebooks
Buying in the Florida Keys is not the same as buying in Miami-Dade or Florida City. The Keys sit in Monroe County, where the county and each municipality write their own short-term rental (STR) ordinances. Miami-Dade has a separate set of rules and processes. If you are comparing a Keys condo to a Florida City townhouse, expect different permits, taxes, and zoning.
Quick snapshot
- In the Keys, every parcel sits either in unincorporated Monroe County or inside a city like Key West, Marathon, Islamorada, Key Colony Beach, or Layton. Each has its own STR rules.
- In Miami-Dade, including Florida City, STRs follow county and city regulations that are distinct from Monroe County.
- Your revenue model will hinge on minimum-stay rules, permit availability, and HOA or condo restrictions. These vary widely by jurisdiction.
Who regulates your rental
For any Keys address, first confirm if the property is in a municipality or unincorporated Monroe County. Use the Monroe County Property Appraiser or a parcel GIS search to verify the exact jurisdiction. This step tells you which planning and code offices control your permit.
Primary local contacts to verify rules and status include:
- Monroe County Planning and Environmental Resources for county STR registration and zoning
- The relevant municipal planning or zoning department if the property sits in Key West, Marathon, Islamorada, Key Colony Beach, Layton, or another city
- The Monroe County Property Appraiser for parcel jurisdiction and land use
- Local tax collector or county finance office for tourist and business tax steps
- The Florida Department of Revenue for state sales tax registration
- Local code enforcement for active or past violations
Tip: Ask for written confirmation from the planning or zoning office that STRs are permitted in the zoning district and whether a current permit exists. Written confirmation carries more weight than a seller’s verbal statement.
Permits and paperwork buyers can expect
Across the Keys and Miami-Dade, the permitting framework is similar in structure but different in details. Plan for a checklist like this and verify exact requirements locally.
Registration and business tax
- Property-specific STR registration or license. Names vary by city: short-term rental permit, transient rental license, or business tax receipt. Many renew annually.
- Display requirements for license numbers in online ads. Some places prohibit advertising if you are not registered.
Local contact and management
- Many ordinances require a designated local contact or manager with a 24/7 phone number to respond to complaints and emergencies.
- If you are out of town, budget for professional local management to meet this standard.
Safety and inspections
- Expect safety requirements such as smoke and CO detectors, exit signage, and flood safety information. Some jurisdictions require an inspection before issuing or renewing a permit.
- Occupancy may be capped by bedroom count or square footage. Keep marketing consistent with the approved occupancy.
Advertising and taxes
- Follow local advertising rules, including posting your registration number on listings.
- Register, collect, and remit both local tourist or occupancy taxes and state sales tax. Confirm with the local tax authority and the Florida Department of Revenue.
Fees, renewals, and enforcement
- Budget for permit fees and renewal costs. Missing deadlines or violating conditions can lead to fines, suspensions, or nonrenewal.
Zoning and minimum stays that shape revenue
Zoning and minimum-stay rules have the biggest impact on nightly rates, occupancy, and your calendar strategy.
- Minimum stays: Some areas require a 7-night, 14-night, or 30-night minimum in specific zones or property types. Others allow nightly rentals. These rules may apply year-round or only during certain seasons.
- Zoning and overlays: Residential neighborhoods, multifamily buildings, or historic districts may limit STRs. Tourist corridors or commercial zones are more likely to allow them.
- Permit caps: Some municipalities limit the number of STR permits in certain areas, making existing permitted units more valuable and harder to replace.
Action step: Ask the planning department to confirm the minimum-stay rule for the parcel’s zoning, whether new permits are currently being issued, and if permits are transferable upon sale.
Condo and HOA rules often decide the outcome
Even when a city or county allows STRs, condo declarations and HOA covenants may set stricter limits or ban short stays. In Keys condo markets, association rules often determine whether your plan is feasible.
Request and review:
- Declarations, bylaws, and house rules related to rentals
- Minimum-stay requirements, seasonal limits, and guest registration procedures
- Any pending amendments that could shorten or eliminate STR rights
- Manager approval processes and fines for violations
Enforcement and risk to your pro forma
Local code enforcement takes STR compliance seriously. Common triggers include operating without a permit, advertising without a license number, failing to collect taxes, repeated nuisance complaints, or safety violations found during inspections.
Consequences can include administrative fines, permit suspension or revocation, and orders to cease renting. Noncompliant properties often lose income while resolving violations, and a history of issues can weigh on underwriting and insurance.
Due diligence checklist before you go under contract
Use this request list to protect your timeline and returns:
- Confirm jurisdiction in the Monroe County Property Appraiser or parcel GIS and identify the controlling city or county office
- Current STR permit or registration if the seller claims rental status
- Written confirmation from the planning or zoning department on allowable STR use, minimum-stay rules, and permit transferability
- Business tax receipt, tourist tax registration, and recent remittance records
- Code enforcement records for any open or past violations
- Condo or HOA documents, including any proposed rule changes under consideration
- Contact details for the local manager or designated local agent
- Insurance policies showing STR coverage and flood coverage where applicable
- Elevation certificate and FEMA flood zone information to estimate flood insurance costs
Financing, insurance, and flood considerations
Lenders, insurers, and associations add another layer beyond municipal rules. Plan early with your team.
- Lending: Some loan programs treat STR income differently or require higher reserves. Confirm with your lender and match your loan type to the property’s use and association rules. Condo restrictions can make a building ineligible for certain loan products.
- Insurance: Many standard homeowner policies exclude commercial STR use. Explore specialty STR policies or endorsements that include liability and guest-related damages.
- Flood risk: Flood insurance is a major variable in the Keys. Compare NFIP and private options, and use elevation certificates to understand pricing. Budget for mitigation steps that can reduce premiums.
Operating playbook for compliance
A practical plan keeps you compliant and protects guest experience.
- Management: If rules require a local contact, engage a manager who can handle 24/7 calls, inspections, and neighbor concerns.
- Marketing: Build your listing around the permitted minimum stay and occupancy. Display required license numbers in all advertising.
- House rules: Include quiet hours, trash procedures, and parking limits consistent with local ordinances and HOA rules. Monitor complaints and respond quickly.
- Reserves: Keep a reserve for inspections, retrofits, and potential fines. Include a buffer for periods when permits are under renewal or temporarily paused.
Trends and policy drivers to monitor
Local rules evolve with housing needs and tourism goals. Expect changes over time.
- Housing availability: Municipalities can tighten rules in response to affordable housing pressures.
- Tourism goals: Policies may shift with seasonal demand and local economic strategy.
- State legislation: Changes at the state level can alter how much control local governments have over STRs. Track proposed bills and rule changes.
Practical steps: Subscribe to Monroe County and municipal planning updates, follow commission agendas, and attend condo meetings. Check code enforcement portals for trends in violations and penalties.
Florida City and Miami-Dade as gateway options
If your goal is to serve Keys visitors without Keys regulations, properties in Florida City or other Miami-Dade areas operate under Miami-Dade and local city rules. The framework, taxes, and zoning differ from Monroe County, so treat this as a separate underwriting model.
How the rules differ
- Different permits: Miami-Dade and Florida City have their own registration, inspection, and advertising requirements.
- Distinct zoning: What is allowed in a Keys tourist corridor may not be allowed in a quiet residential area in Miami-Dade, and vice versa.
- Taxes and enforcement: Tax registrations and enforcement processes run through Miami-Dade and the city, not Monroe County.
When a Miami-Dade property makes sense
- You want easier access to the mainland and national parks, or you plan to serve travelers who road trip into the Keys
- You prefer a different regulatory mix than a Keys municipality with strict minimum stays or permit caps
- Your condo or HOA in Miami-Dade allows a rental plan that matches your target stays and occupancy
How to pick winners and avoid pitfalls
Use this simple approach to protect your investment:
Start with zoning and minimum stays. If a seven-night minimum breaks your pricing model, pivot early.
Confirm permit availability. A cap or moratorium can turn a great unit into a long-term hold with no STR income.
Read the condo or HOA rules before you tour. Association restrictions often decide the outcome.
Stress test underwriting. Model seasonality, potential downtime for inspections or renewals, and a temporary regulatory pause.
Line up insurance and management. Confirm STR coverage and local contact requirements to avoid last-minute delays.
Ready to evaluate a specific property or compare the Keys with Florida City? Let’s build a compliant plan that fits your goals and timeline.
If you want a boutique, hands-on strategy and clear next steps, reach out to Dania Perez for a personalized consultation.
FAQs
What are Florida Keys vacation-rental rules and who sets them?
- In the Keys, Monroe County and each city like Key West or Marathon set their own rules, so you must verify both the county and municipal ordinances for the specific parcel.
How do minimum-stay rules impact my STR revenue in the Keys?
- Minimum stays such as 7, 14, or 30 nights can limit booking frequency and pricing; confirm the exact rule for the property’s zoning before modeling cash flow.
Do condo or HOA rules override city or county STR permissions?
- Yes. Associations often impose stricter limits or bans, so condo documents can be the deciding factor even if local law allows STRs.
What taxes do I need to collect for a Keys short-term rental?
- Expect to register for local tourist or occupancy taxes and state sales tax, then collect and remit both according to local and state requirements.
What happens if I operate an STR without the proper permit in the Keys?
- You risk fines, permit denial or revocation, and cease-and-desist orders, which can halt income and complicate future renewals.
How do Miami-Dade and Florida City STR rules differ from the Keys?
- They use separate county and city processes, zoning, tax registrations, and enforcement systems, so treat them as a distinct regulatory model.
