Current permit-cap status, minimum-stay requirements, owner-occupancy rules, and jurisdiction breakdown for short-term rentals in Winter Park. Every field is cited to a primary source below. Always verify the specific parcel with the operating jurisdiction before writing an offer.
Winter Park requires STR registration under Chapter 10 of the Town Code plus a mandatory East Grand Fire District Life & Safety Inspection every 12 months (Ordinance 624); a $400-per-bedroom annual affordable-housing surcharge (Ord. 605) applies on top of the $150 base fee.
Have a specific property in mind? Analyze it with a $99 report →Winter Park's STR framework has grown teeth. Ord. 552 (2021-03-16) established the registration program; Ord. 574 (2022-03-29) added penalty structure; Ord. 605 introduced a $400-per-bedroom annual fee earmarked for workforce housing; Ord. 624 mandates that all STR registrations and renewals show proof of a passing East Grand Fire District Life & Safety Inspection completed within the prior 12 months (effective 2025-08-01). Registration number must appear in every listing. Underwrite operating cost around the per-bedroom fee — a 4-bedroom cabin owes $1,600/yr in housing fee alone before the $150 base registration and $100 fire-inspection fee.
Short-term rentals in Winter Park are classified as restricted as of 2026-08-16. Winter Park requires STR registration under Chapter 10 of the Town Code plus a mandatory East Grand Fire District Life & Safety Inspection every 12 months (Ordinance 624); a $400-per-bedroom annual affordable-housing surcharge (Ord. 605) applies on top of the $150 base fee.
Not clearly documented in the primary source. No numeric town-wide cap in Chapter 10 as of verification date. Compliance friction (annual fire inspection + bedroom-based fee) is the practical throttle.
The primary source does not specify a minimum stay for short-term rentals.
Winter Park does not require owner-occupancy for short-term rental operators as of 2026-08-16. Verify the specific parcel with the operating jurisdiction before offering, as owner-occupancy rules interact with zoning overlays.
Contact the operating jurisdiction directly using the primary-source links published on this page. Zoning, HOA restrictions, and pending regulatory changes are parcel-specific and can override the citywide profile above. DepreciMax's $99 property report separately sizes the Year-1 §168(k) bonus depreciation deduction for a specific address, once regulatory clearance is confirmed.
Once you've verified the regulatory profile of a listing you're considering, run a $99 DepreciMax property report to size the actual Year-1 §168(k) bonus depreciation deduction. The report analyzes the listing photos to classify finishes as 5-year personal property, 15-year land improvements, or 39-year structural — producing a line-item estimate closely calibrated to a formal cost seg study.
Use the DepreciMax STR Regulations Database for the full top-50 market fleet — every market cited to a primary jurisdiction source, updated quarterly.
Not legal or tax advice. Short-term rental regulations change frequently and vary by parcel, zone, and HOA. The information on this page is a summary of publicly available primary sources as of 2026-08-16. Before acting — buying, listing, or operating a short-term rental in Winter Park — verify current rules with the operating jurisdiction and consult a local attorney and CPA.