Practical checklist

• Confirm property is inside Windsor Hills STRPD and city/county. Windsor Hills Official Rentals

•  Apply / obtain State (DBPR) license or submit application. Osceola County

• Complete & submit Local Business Tax Receipt (Osceola Tax Collector or Kissimmee BTR). osceolataxcollector.org+1

•  Gather: deed, owner ID, floor plan, insurance certificate, 24/7 contact. osceolataxcollector.org

• Schedule and pass required inspection (building/fire/safety). Osceola County

• Register property/guests with Windsor Hills gatehouse/resort office. windsorhillsresortfl.com+1

•  Register for sales & tourist taxes; set up remittance. osceolataxcollector.org+1

•  Purchase STR insurance and confirm platform/resort requirements. BNB Calc+1

•  Add house rules, guest packet, emergency procedures, and local manager contact. windsorhillsprivaterentals.com

Timing & estimated order (typical, but confirm locally)

• Confirm STRPD zoning & resort registration (1–3 days). Windsor Hills Official Rentals

• Prepare documents and apply for state license & LBTR simultaneously (1–2 weeks depending on forms). osceolataxcollector.org+1

• Schedule inspection and resolve any issues found (1–3 weeks depending on corrections). Osceola County

• Get final approvals, register guests with Windsor Hills, then go live (after approvals).

Tips from experience

• Do the resort registration early — Windsor Hills gate procedures are strict and guests need pre-registration to avoid entry delays. windsorhillsresortfl.com

• Have a local emergency contact (person who can arrive within 30–60 minutes) — Osceola requires it and it’s also a resort expectation. BNB CalcKeep proof of insurance & license on file and available for Windsor Hills management or any platform audits. Windsor Hills Official Rentals+1

Required Forms & Application Links (Your STR Packet)

Purpose / Document

What You Need / What It Does

Direct Link / Notes

State-level Vacation Rental License (from Florida Department of Business and Professional Regulation — DBPR)

Required if you rent out the entire unit more than 3 times/year (or otherwise hold out as a public lodging). Must be obtained before county/local licensing. My Florida License+2MyFloridaLicense+2

Downloadable application PDF: DBPR HR‑7028 Vacation Rental License Application My Florida License

County Business Tax Receipt (BTR / LBTR) via Osceola County Tax Collector

Short-term rental business receipt required to operate legally. Must accompany copy of state license or license application. osceolataxcollector.org+2osceolataxcollector.org+2

Fill out: Application for Osceola County Local Business Tax Receipt – Short/Long Term Rental osceolataxcollector.org+1

Osceola County STR / Short-Term Rental License & Inspection

County requires initial inspection (safety/building code compliance) before license is issued. BNB Calc+1

Use the county’s: Osceola County Building and Permitting Office “Online Permit Center” to schedule inspection and apply. Osceola County+1

Tourist Development Tax Registration & Reporting Forms

You must collect and remit state sales tax + Osceola County Tourist Development Tax for guest stays under 6 months. osceolataxcollector.org+2https://mikechenrealtor.com+2

Downloadable from Osceola County Tax Collector’s website under “Tourist Development Taxes” section. osceolataxcollector.org

 Step-by-Step “How to Fill & Submit” (Your Packet Workflow)

Download and complete the DBPR Vacation Rental License application (HR-7028)

Submit online via DBPR’s portal. MyFloridaLicense+1

1. Once processed, DBPR will issue a state license — you’ll need the license number for county/local applications.

2. Download and complete the Osceola County Local Business Tax Receipt (LBTR) application

3. Use the “Short/Long Term Rental” version. osceolataxcollector.org+1

4. Attach a copy of your state license (or DBPR application if pending). osceolataxcollector.org+1

5. Schedule & pass the required county inspection

6. Using the Osceola County Building & Permitting Office’s Online Permit Center account, request an inspection for STR compliance. Osceola County+2Lodge Compliance+2

7. Inspection typically checks for compliance with building, safety, egress/fire, etc. BNB Calc+1

8. Apply/submit LBTR + pay any required fees once inspection passes

9. If property is within unincorporated Osceola County, submit to Osceola County Tax Collector’s office. Osceola County+2osceolataxcollector.org+2

10. If in city limits (e.g. Kissimmee), also check for city-level BTR or permit requirements. Kissimmee+1

11. Register for and set up tax collection/remittance

12. Register with the state for sales & use tax (for transient lodging).

13. Register with Osceola County for Tourist Development Tax (6% for stays under 6 months) and learn the remit schedule. osceolataxcollector.org+2https://mikechenrealtor.com+2

14. Ensure ongoing compliance: maintain guest register, safety compliance, renewals

15. Most licenses / BTRs need annual renewal. For county BTR, the receipt expires every September 30. osceolataxcollector.org+1

16. Maintain documentation: proof of insurance, safety equipment (smoke detectors, fire extinguishers), contact info for property manager/owner, guest logs, etc. (per STR regulatory requirements) Lodge Compliance+2https://mikechenrealtor.com+2

 What to Include in Your Packet Folder

• Filled-out DBPR Vacation Rental License Application (HR-7028)

• Copy of state license (once issued) or application confirmation

• Filled-out Osceola County LBTR application form

• Proof of property ownership (deed/tax bill), owner ID, insurance certificate

• Floor plan + safety equipment layout (smoke detectors, fire extinguishers, exits) — helpful for inspection

• Contact information (owner/manager, local emergency contact)

• Copy of inspection request / permit from Osceol County (once scheduled)

• Tax registration paperwork (state sales tax, Osceola Tourist Development Tax)

• Guest registration/house rules/operation protocol (especially for resort rules if in a resort like Windsor Hills)

 Where to Get the Official PDFs & Links (Download Direct)

• DBPR Vacation Rental License (HR-7028) — official PDF application from DBPR site. My Florida License+1

• Osceola County Short/Long Term Rental LBTR Application — directly from Osceola County Tax Collector’s website. osceolataxcollector.org+1

• Osceola County Building & Permitting “Online Permit Center” — for scheduling inspection/permits. Osceola County+1

• Osceola County Tourist Development Tax / Tax Collector Tax Forms — available via County Tax Collector’s “Tourist Development Taxes” section. osceolataxcollector.org+1