Winter Park Short Term Rental

Investment Overview

100Units.com presents a rare hospitality-yield opportunity in Winter Park's Class A core, directly in the Hillstone trade area on South Orlando Avenue. The offering consists of 12 short-term rental units — 8 studios and 4 one-bedroom/one-bath — plus a street-facing office suite fronting S. Orlando Ave. For a buyer who knows this location, the thesis is straightforward: Winter Park generates year-round, non-theme-park demand — Rollins, Park Avenue, AdventHealth Winter Park, and the corporate and event traffic that fills the surrounding hotels at rates a 12-unit boutique operation can match without a hotel's cost structure. Supply of legally operating short-term rental product in this submarket is effectively fixed, which is the real barrier to entry here. The value-add is in operations, not entitlement: professionalize the unit finishes, reposition to a branded boutique STR platform, and capture the spread between long-term rents and nightly rates. The office suite adds a separate income stream or on-site management and check-in presence.

Investment Highlights

• Boutique short term rental asset in A class Winter Park, FL
• Immediate value creation opportunity through repositioning
• Proven hospitality layout ready for new ownership
• Year-round demand, independent of theme-park seasonality