You bought a vacation home at Windsor Cay Resort. Before your first guest books a single night, three things need to be in place: a state license, a tax registration, and a basic understanding of what your property manager handles versus what stays on you.
The good news? Windsor Cay is a purpose-built short-term rental community. You will not fight city zoning boards or apply for special use permits like owners in Orlando or Kissimmee. But you still need a Florida vacation rental license from the state, and the tax registration that comes with it.
This guide walks you through every step, with exact costs and timelines for 2026.
Why Windsor Cay Owners Have It Easier
Most Florida vacation rental owners spend weeks navigating local ordinances, zoning restrictions, and city permit applications. Windsor Cay skips that entire layer. The community was designed for short-term rentals. Your deed allows nightly rentals. The HOA accommodates vacation rental operations. There are no city-level permits to worry about.
If you are comparing ownership costs at Windsor Cay to communities with STR restrictions, this is a significant financial and time advantage. What remains is the state-level process: a DBPR vacation rental license and Florida tax registration.
Apply for Your DBPR Vacation Rental License
The Florida Department of Business and Professional Regulation (DBPR) requires every property rented for periods under 30 days to hold a vacation rental license. No exceptions for resort communities. No exceptions for properties managed by a company.
How to Apply
Go to myfloridalicense.com and create an account. The license type you need is Vacation Rental Dwelling Single, which covers one single-family home or townhome used as a short-term rental.
The application is Form HR-7028. It asks for your property address, ownership details, and confirmation that the property meets basic safety requirements. Most owners complete it in under 20 minutes.
What It Costs
Per year, single unit
$170 license fee + $50 application fee + $10 HEP fee
A half-year application runs $150 if you are applying within six months of your district’s renewal date.
How Long It Takes
Online applications are typically processed in 1 to 2 business days. Your digital license arrives by email with a license number and expiration date. No initial inspection is required. DBPR may conduct random or complaint-based inspections after the license is active, but there is no pre-approval visit.
That license number is what Airbnb and VRBO now require on Florida listings. Without it, your listing can be flagged or removed.
Deciding between self-managing or bringing in help? Owners who choose hiring a property manager still need the DBPR license in their own name. The manager handles operations, but the license responsibility stays with the owner.
Register for Florida Taxes
Once your Florida vacation rental license is approved, register with the Florida Department of Revenue. This is where your tax obligations get set up.
The Tax Breakdown
Windsor Cay sits in Lake County. Here is what you owe on every dollar of rental income:
| Tax | Rate | Filed With |
|---|---|---|
| Florida state sales tax | 6% | FL DOR |
| Lake County discretionary surtax | 1% | FL DOR |
| Lake County tourist development tax | 4% | FL DOR |
| Total | 11% | All filed with FL DOR |
Lake County is a non-self-collecting county. That means you register once with the Florida Department of Revenue and file everything in one place. You do not need to register separately with the Lake County Tax Collector, unlike owners in some other Florida counties.
What Airbnb Handles (and What It Does Not)
Here is the part most new owners miss: Airbnb collects and remits all three taxes for bookings made through their platform in Lake County. If 100% of your bookings come through Airbnb, the platform handles your tax collection and payment automatically.
But you still must register with the Florida Department of Revenue. And if you list on VRBO, Booking.com, or take direct bookings, you are responsible for collecting and remitting the full 11% yourself.
Owners who work with professional vacation home management companies like FunStay Florida get this handled across all platforms. FunStay collects taxes on every booking regardless of the channel and remits them on your behalf.
Handle the Details Most Owners Forget
The DBPR license and tax registration cover 90% of your compliance. A few smaller items round out the picture.
Business Tax Receipt
Depending on your specific location within Lake County, you may need a local business tax receipt (formerly called an occupational license). Check with the Lake County Tax Collector’s office. The fee is typically minimal.
Insurance
Standard homeowner’s insurance does not cover short-term rental activity. You need a policy that specifically covers vacation rental operations, or a rider added to your existing policy. Operating without proper coverage, even with a valid Florida vacation rental license, leaves you exposed. Many factors that affect Airbnb income are within your control, but an insurance gap is a risk you cannot recover from.
Annual Renewal
Your DBPR license expires annually. Renewal is done through the same myfloridalicense.com portal. Set a reminder 60 days before expiration. A lapsed license means your listing can be pulled and fines start at hundreds of dollars per violation.
5 Licensing Mistakes Windsor Cay Owners Make
Before you hire a vacation rental agent in Clermont FL, ask these five questions. The answers will tell you whether they’re a specialist or a generalist wearing an investor hat.
Assuming Airbnb handles everything
Airbnb collects taxes in Lake County, yes. But you still need the DBPR vacation rental license in your name and a Florida DOR registration on file. The platform does not handle licensing.
Not registering with the Florida DOR
Even if Airbnb remits your taxes, the state expects you to have an active tax registration. Skipping it creates problems during audits.
Letting the license lapse
Annual renewal is not optional. A lapsed DBPR license exposes you to fines and listing removal. Owners managing their vacation home remotely sometimes lose track of renewal dates.
Waiting until after the first booking
Your license must be active before you host a single guest. If you are evaluating townhome vs single-family ROI before buying, factor in that licensing starts at closing, not when your first guest arrives.
Citing dead legislation as current requirements
Florida HB 79, a proposed pool safety bill, died in the legislature on March 13, 2026. It did not become law. Some online guides still reference it as active. Do not rely on outdated sources.
How a Property Manager Handles Compliance for You
If you work with a full-service vacation rental manager, the compliance burden shrinks dramatically. Here is what a company like FunStay Florida handles:
✓ Tax collection on every booking
✓ Monthly tax remittance to FL DOR
✓ License renewal reminders
✓ Insurance coordination
✓ Guest safety compliance
✓ Multi-platform coverage
The one thing a manager cannot do for you: hold the DBPR license. That stays in the owner’s name regardless. But everything else, from the FunStay Homes track record to daily operations, runs through the management company.
For international buyers purchasing at Windsor Cay, this is especially valuable. The licensing process is identical for foreign owners, but having a local manager ensures nothing falls through the cracks.
Total Licensing Cost Summary
| Item | Cost | Frequency |
|---|---|---|
| DBPR vacation rental license | $230 | Annual |
| Florida DOR tax registration | Free | One-time |
| Business tax receipt (if required) | ~$25-50 | Annual |
| Total licensing cost | ~$255-280/yr |
Compare that to operating without a license: fines starting at $500 per violation, listing removal, and denied insurance claims. The $230 annual fee is less than one weekend booking at Windsor Cay.
For the full picture of recurring expenses, see the HOA and property tax breakdown for Windsor Cay.
Get Licensed and Start Earning
Mike Chen helps Windsor Cay buyers navigate licensing, tax registration, and property management setup from day one. He owns 10 vacation rental properties himself and manages roughly 100 through FunStay Florida.
Frequently Asked Questions
How do I get a Florida vacation rental license?
Apply through the DBPR at myfloridalicense.com using form HR-7028. Select “Vacation Rental Dwelling Single” as your license type. The total cost is $230 per year ($170 license fee + $50 application fee + $10 HEP fee). Online applications are processed in 1 to 2 business days with no initial inspection required.
How much does a Florida vacation rental license cost?
A single-unit Florida vacation rental license costs $230 for a full year or $150 for a half-year application. The breakdown is $170 for the license fee, $50 for the application fee, and $10 for the Hospitality Education Program fee. Renewal is annual at the same rate.
Do I need a license to rent my Windsor Cay home on Airbnb?
Yes. Florida Statute 509.241 requires a DBPR vacation rental license for any property rented to guests for periods under 30 days more than three times per year. Windsor Cay’s STR-friendly zoning eliminates local permit requirements, but the state license is mandatory. Airbnb now requires a valid license number on Florida listings.
What taxes do Florida vacation rental owners pay?
Windsor Cay owners in Lake County pay 11% total on rental income: 6% Florida state sales tax, 1% Lake County discretionary surtax, and 4% Lake County tourist development tax. All taxes are filed with the Florida Department of Revenue. Airbnb collects and remits these taxes automatically for bookings made through their platform.
How long does it take to get a Florida vacation rental license?
Online applications submitted through myfloridalicense.com are typically processed in 1 to 2 business days. The digital license is emailed after approval. No initial property inspection is required. Paper applications take longer.
Does my property manager need a separate license?
No. The DBPR vacation rental license is held in the property owner’s name, not the manager’s. Your property manager handles operations, tax collection, and remittance, but the license stays with you as the owner. You are responsible for keeping it current.
What happens if I operate without a Florida vacation rental license?
Operating an unlicensed short-term rental in Florida exposes you to fines starting at $500 per violation from DBPR, potential listing removal from booking platforms, and denied insurance claims. The $230 annual license fee is a fraction of one weekend’s rental income at Windsor Cay.
Does Airbnb collect taxes for Windsor Cay owners?
Yes. Airbnb collects and remits all three applicable taxes (state sales tax, county surtax, and tourist development tax) for Lake County bookings. However, you must still register with the Florida Department of Revenue. If you also list on VRBO, Booking.com, or accept direct bookings, you are responsible for tax collection on those channels.
Whether you are buying your first Airbnb investment home near Disney or adding to an existing portfolio, Mike walks you through compliance before the ink dries on closing. Buying without an STR-specialized realtor is one of the top investment property red flags. Licensing is just one of many details a general agent will miss.
Mike Chen | La Rosa Realty Celebration | 503-888-8070
