Islamorada, FL Short-Term Rental Checklist (Free, Printable)

📋 The Basics

Can I rent my place short-term here?: Only in some areas
Do I need a permit?: Yes. You need a yearly Village Vacation Rental License.
What taxes do I pay?: Total about 12.5%. Airbnb collects some; you pay Monroe County's 5% tourist tax yourself.

Your 3 steps to be legal

Get a Florida state rental license (DBPR) and sign up for Florida sales tax.
Check your land-use category and sign up for Monroe County tourist tax.
Get the Village license and pass a safety inspection.

⚠️ Biggest risk: Renting for less than 7 days outside a Tourist Commercial zone.

Words confusing? See the glossary. Details and official sources are below.

This is the general rule for Islamorada. Does your address qualify?

The free info covers the city as a whole. Your property can still be different: zoning can change from one street to the next, and an HOA or condo ban can stop rentals even where the city allows them.

Your $49 Compliance Check looks at your exact property:

Whether your exact address and zone allow short-term rentals
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Which permits and tax accounts you personally need
What you're missing right now
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Permit / license / registration

State license (Florida DBPR): Florida DBPR vacation rental / transient public lodging license (homestead room-rental exemptions may apply).
State licenses: Florida DBPR vacation rental license and FL Department of Revenue sales tax registration are required for all Florida vacation rentals.
License: An annual Islamorada Vacation Rental License is required for rentals of 28 days or less (Village Code Ch. 30, Secs. 1291-1299), only in allowed land-use categories; apply through the CityView portal and pass a life-safety inspection.

Zoning, where allowed & definitions

State preemption: Florida law (s. 509.032(7)(b), F.S.) bars local rules adopted after June 1, 2011 from prohibiting vacation rentals or regulating rental duration/frequency; older local rules still apply.

Night limits, minimum stays & occupancy

Minimum stay: No vacation rental may be for less than 7 days unless in a Tourist Commercial (TC) zoning district.
Occupancy & parking: Max two adults per bedroom (children over 6 count as adults); vehicles only in designated on-site spaces; a property manager and secondary contact are required.

Fees, penalties & pending changes

Fees: Verify with the Village for the current license fee.

Taxes & who collects them

Register / account for FL state sales tax (6%)
Register / account for Monroe County surtax (1.5%)
Register / account for Local tourist/transient taxes (5%)
What Airbnb collects: Airbnb collects state 6% + 1.5% surtax only. You must register with and remit Monroe County's 5% tourist development tax yourself.
Vrbo and direct bookings: check which taxes Vrbo collects in your area; for direct bookings you collect and remit all of them yourself.
Mandatory cleaning fees charged to guests are taxable as part of the rental (state, surtax and tourist tax). Only an optional, separately itemized fee the guest can decline is excluded (FL Admin. Code 12A-1.061).

Total rate: 12.5%. Monroe County tourist development tax 5% (FL DOR DR-15TDT); surtax 1.5% (DR-15DSS). Calculate.

HOA / condo check

Read your declaration, bylaws and rules for rental bans, minimum terms, caps and approval requirements.
Get any association sign-off or approval letter your city or association requires.
See our HOA & condo guide.

Insurance

Confirm your homeowner/condo policy covers short-term rental use, or add a short-term rental policy. Platform host protection is not a substitute for insurance.
Ask your association whether it requires specific liability coverage.

Deadlines

Renew city/county permits or registrations on their schedule (often annually): confirm the date with the office that issued it.
Florida sales and transient rental tax returns: due the 1st, late after the 20th of the month after the reporting period.
Property tax dates: see Florida deadlines.

Official sources

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Is my Islamorada rental legal? Checklist