Within Hollywood, the 33021 zip code emerges as a particularly attractive cluster for investors seeking above-market returns. Here, 117 listings post a median annual revenue of $66,983, supported by a $345 ADR and 59% occupancy—yielding a standout 15.0% gross yield on a $445,147 median home value. The 33019 area, which encompasses the bulk of Hollywood Beach, is the city’s short-term rental engine, with 1,815 listings averaging $54,385 in annual revenue at a $230 ADR and 56% occupancy. While yields here (10.9%) are slightly below the city median, the sheer scale and liquidity of the segment make it a core play for operators seeking volume and established demand. For tailored acquisition strategies or on-the-ground insights, a Chalet agent can provide granular product-level data.
Product segmentation by bedroom count reveals a clear step-up in revenue potential as property size increases. Two-bedroom units (29% of supply) average $44,660 annually at a $280 ADR, but the three-bedroom segment (10% of supply) closes the gap with the market average at $57,402 and a $357 ADR. Four-bedroom properties (5% of supply) outperform with $70,354 in average annual revenue and a $465 ADR, though occupancy dips to 50%. Investors with the capital and operational sophistication to manage larger homes can tap into the five-bedroom segment, which delivers $79,787 in annual revenue at a $604 ADR—though again, occupancy holds at 50%. Thin sample sizes above five bedrooms limit statistical confidence, but the trend is clear: scale drives revenue, provided operators can manage seasonality and compliance risk.
The Hollywood short-term rental market rewards professionalization and operational discipline. International guests account for nearly 20% of bookings, with Miami, New York, Atlanta, Orlando, and Chicago as key domestic feeder markets. Booking lead times average 42 days (median 22), and the typical stay approaches six nights—factors that favor operators with strong calendar management and guest screening protocols. Top hosts such as Stay Sol Six and RoomPicks have achieved scale through portfolio aggregation, but the market remains fragmented, with the top 10 hosts controlling just 16.9% of listings. For investors modeling returns or stress-testing acquisition scenarios, the Chalet ROI calculator provides scenario-driven analytics grounded in current market data.
Risks are real and concentrated. Hollywood’s short-term rental revenue per listing surged by 34.6% year-over-year (Mar–May 2026 vs. Mar–May 2025), powered by a 25.9% jump in ADR and a 2.0% increase in occupancy, even as listing supply contracted by 13.2%. However, median home values fell 6.0% over the same period, and the city’s regulatory climate is among the strictest in Florida. Three separate licenses are required, enforcement is active, and violations can result in permanent license loss. The September trough (45% occupancy, $2,350 revenue) is a stress test for cash flow and compliance. Investors must navigate these hurdles with rigor—review Hollywood STR regulations before committing capital.
Hollywood, FL’s short-term rental market is a high-reward, high-discipline environment—investors who master seasonality, compliance, and professional operations can capture outsized returns, but the margin for error is narrow.
