Short answer: only for street placement. Orlando's City vs. County jurisdictions and multi-county metro add local complexity. Here's what applies to your project.
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Many "Orlando" addresses are actually in unincorporated Orange County — not City of Orlando jurisdiction. Unincorporated Orange County permits come from Orange County Public Works. Your operator will know which applies based on your address. A quick check: if your utilities come from Orange County rather than the City of Orlando, you're unincorporated.
For Kissimmee (Osceola) and Sanford/Lake Mary (Seminole), permits come from those counties' public works departments — separate from City of Orlando. Similar rules and fee structures ($40–$85). Most operators who service those areas handle the local permit process routinely.
No. Driveway or private property placement requires no permit. The permit requirement only applies for street or right-of-way placement.
Check your utility bills — Orange County Utilities vs. the City of Orlando is the clearest indicator. Your operator will also know based on your address.
Same rule — driveway placement needs no permit. Street placement requires one. Most vacation rental renovation uses driveway or parking lot placement, which avoids the permit process entirely.