Winter Park, FL Airbnb Market Data, Statistics, and Occupancy Rates

Winter Park Short-Term Rental Market Overview

Winter Park, FL sits in the heart of Orlando's metro area, drawing visitors year-round with its charming dining scene, proximity to major theme parks, and a steady flow of business travelers. With an average daily rate of $186 and occupancy at 55% — just above Florida's state average — the market delivers roughly $28,567 in annual revenue per listing. However, average home values near $1.08 million mean the revenue-to-price ratio is tight, making careful deal sourcing essential for investors looking to generate meaningful cash flow.

Key Market Statistics

According to Rabbu market data, the Winter Park short-term rental market shows:

Data sources: Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026.

Why Investors Consider Winter Park

Winter Park attracts investor attention thanks to its above-average occupancy stability and central Florida location, though elevated home prices demand more selective acquisitions to achieve strong returns.

Expert Market Assessment

"Winter Park presents a competitive opportunity where strong guest demand meets elevated entry costs. The market's 55% average occupancy and $186 ADR are respectable, but with average home values above $1 million, investors need to target properties where revenue can stretch further — particularly 2- and 3-bedroom units that hit the sweet spot of occupancy and nightly rate. Seasonality is moderate: March stands out as the clear peak at $3,722 in average revenue, while September dips to $1,487, creating a spread that's manageable but worth planning for. Investors who source wisely and optimize for the amenities guests expect here can find workable deals, but this isn't a market where any property will pencil out."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Winter Park

Average revenue by month in Winter Park

March is the standout peak at $3,722 in average revenue, nearly 2.5 times the September low of $1,487. The winter holiday season also performs well with December at $2,771, while summer months hover around $2,000–$2,400, indicating moderate but not extreme seasonality.

Active Airbnb listings by property size in Winter Park

One-bedroom listings dominate the supply with 32 of 84 total active listings, followed by 3-bedrooms at 24. Four-bedroom properties are notably scarce with only 6 listings, which could represent a supply gap for investors targeting higher-revenue configurations.

Average daily rate (ADR) by property size in Winter Park

ADR nearly doubles from 1-bedroom ($103) to 2-bedroom ($191) and continues climbing to $236 for 3-bedrooms, but the jump to 4-bedrooms ($240) is minimal. The strongest rate premium relative to the step up in size appears at the 2-bedroom level.

Average RevPAN by property size in Winter Park

Three-bedroom properties deliver the highest RevPAN at $142, outperforming both 2-bedroom and 4-bedroom units (each at $120) and significantly exceeding 1-bedrooms at $48. This makes 3-bedroom configurations the most efficient earners per available night after factoring in occupancy.

Average occupancy rates by property size in Winter Park

Two-bedroom units lead occupancy at 63%, followed closely by 3-bedrooms at 60%, while 4-bedrooms (50%) and 1-bedrooms (47%) lag behind. For investors prioritizing consistent bookings and cash-flow predictability, the 2- and 3-bedroom range offers the most reliable fill rates.

Average monthly revenue by property size in Winter Park

Monthly revenue scales steadily from $1,310 for 1-bedroom units to $4,143 for 4-bedrooms, with 3-bedroom properties averaging $3,473. The jump from 1- to 2-bedroom ($1,310 to $2,490) is the most dramatic proportional increase, making 2-bedrooms an attractive entry point.

Average annual revenue by property size in Winter Park

Four-bedroom properties top the market at $49,716 in average annual revenue, while 3-bedrooms generate $41,686 — both figures that may better support the math on Winter Park's higher property values. One-bedroom units averaging $15,728 annually will struggle to justify acquisition costs at current home prices.

Most common amenities for Airbnb listings in Winter Park

Parking (98%) and kitchen access (92%) are near-universal, reflecting guest expectations in a suburban Florida market where most visitors arrive by car. The prevalence of workspace amenities (64%) and self check-in (74%) signals a market that caters to both remote workers and independent travelers, while pool access at just 27% suggests an opportunity for differentiation.

Understanding Winter Park's ROI Score: 39/100

Rabbu's ROI Score is a proprietary metric that evaluates short-term rental investment potential based on multiple factors.

How the ROI Score is Calculated

What This Means for Investors

Winter Park's ROI Score of 39 out of 100 places it in the 'Competitive Opportunity' band, reflecting a market where demand is real but entry costs are high relative to revenue. Occupancy stability scores above average, which is encouraging for cash-flow consistency, but the below-average revenue-to-price ratio and supply/demand balance signal that not every property will pencil out. Investors should pair this data with thorough local regulatory research and focus on property sizes and configurations — like 3-bedroom units — where the numbers are most favorable.

Short-Term Rental Regulations in Winter Park

Understanding local STR regulations is essential before investing in Winter Park. Here's the current regulatory landscape:

Permit Requirements

The City of Winter Park and the State of Florida generally require short-term rental operators to register or obtain a permit before listing a property. Investors should verify current permit and licensing requirements directly with the City of Winter Park and the Florida Department of Business and Professional Regulation, as rules can change.

Key Restrictions

Common restrictions in Florida STR markets include occupancy limits based on property size, minimum stay requirements in certain residential zones, noise ordinances, and parking regulations. HOA and community deed restrictions may impose additional limitations or outright prohibit short-term rentals, so reviewing governing documents before purchasing is critical.

Tax Obligations

Short-term rental hosts in Florida are typically subject to state sales tax and county-level tourist development taxes on booking revenue. Many platforms collect and remit these taxes automatically, but operators should confirm compliance with Orange County and state requirements to avoid penalties.

Regulations subject to change. Always verify with local authorities before purchasing. A Rabbu partner agent specializing in Winter Park can provide current regulatory guidance.

Future Outlook & Long-Term Forecast

"Over the next 12–18 months, Winter Park's STR market is expected to maintain steady demand, particularly during its strong spring season when monthly revenues can exceed $3,700. Occupancy stability rates above average for the area, which suggests consistent guest interest even outside peak months. ADR may see modest increases in the 1–3% range as the listing count — which grew 127% year-over-year — begins to stabilize. Investors should anticipate that the growing supply could put some downward pressure on occupancy and pricing power, so differentiation through property quality and amenities will matter more than ever."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Winter Park, FL

What is the average Airbnb occupancy rate in Winter Park?

The average occupancy rate for Airbnb listings in Winter Park is currently 55%, which is slightly above the Florida state average of 54%. Occupancy varies by property size — 2-bedroom units lead at 63%, while 1-bedroom units average 47%. These figures reflect trailing 12-month performance across active comparable listings.

How much do Airbnb hosts make in Winter Park?

On average, Airbnb hosts in Winter Park earn approximately $2,380 per month or $28,567 per year based on trailing 12-month booking data. Revenue varies significantly by property size: 1-bedroom listings average about $15,728 annually, while 4-bedroom properties can reach roughly $49,716 per year. Actual earnings depend on factors like property quality, pricing strategy, and seasonal demand patterns.

Is Winter Park a good market for Airbnb investment?

Winter Park carries a Rabbu ROI Score of 39 out of 100, classified as a 'Competitive Opportunity.' Occupancy stability is above average, and market growth trends are steady, but the high average home value of $1,082,582 compresses the revenue-to-price ratio. Investors who source deals below the market average or target high-performing property sizes (like 3-bedroom units earning ~$41,686/year) may find the numbers more attractive. Thorough deal-level analysis is recommended.

What is the average daily rate (ADR) for Airbnb in Winter Park?

The average daily rate across all active Airbnb listings in Winter Park is $186, which is well below the Florida state average of $498. ADR scales with property size: 1-bedroom listings average $103 per night, 2-bedrooms average $191, 3-bedrooms average $236, and 4-bedrooms average $240 per night.

Are short-term rentals legal in Winter Park?

Short-term rentals operate in Winter Park, FL, but hosts are generally required to obtain appropriate permits and comply with local and state regulations. Requirements may include business licenses, state registration through the Florida DBPR, and adherence to zoning, noise, and occupancy rules. Investors should verify the latest rules with the City of Winter Park and consult with a local attorney or real estate professional before purchasing.

When is peak season for Airbnb in Winter Park?

March is the clear peak month for Airbnb revenue in Winter Park, with average earnings reaching $3,722 — driven by spring break travel and seasonal tourism. December ($2,771) and February ($2,672) also perform well above the annual average. The slowest month is September, when average revenue dips to $1,487, making it a good time for maintenance and property improvements.

How many Airbnbs are there in Winter Park?

As of April 2026, there are 84 active Airbnb listings in Winter Park. One-bedroom units make up the largest share with 32 listings, followed by 3-bedrooms (24), 2-bedrooms (18), and 4-bedrooms (6). Notably, the listing count has grown 127% year-over-year, indicating significant new supply entering the market.

How is Airbnb revenue calculated in Winter Park?

The annual and monthly revenue figures shown for Winter Park are derived from the trailing 12 months of historical booking performance for active comparable Airbnb listings in the market — they are not forward-looking projections. We average each comparable listing's actual revenue per available night (RevPAN) by month over the past year, remove regional outliers, and roll the results up to a market-level historical average. Because each month uses its own historical data, the figures naturally reflect seasonal peaks (like March) and slower periods (like September). Individual results can vary meaningfully based on property quality, pricing strategy, and how well a listing is managed.

About Rabbu Market Data

Rabbu provides Airbnb and short-term rental market data and statistics across the United States. Our mission is to empower investors with accurate insights and easy-to-use tools, so they can confidently identify and act on the best opportunities in the Airbnb market.

What this data includes

• Regularly updated active Airbnb and STR listing counts for Winter Park and surrounding zip codes
• Average daily rate, occupancy, and RevPAN trends across property sizes
• Monthly and annual revenue figures based on trailing 12-month booking performance
• Home value data sourced from Zillow Home Value Index (ZHVI) for acquisition benchmarking
• Supply distribution and popular amenity data to inform property configuration decisions

Sources and disclaimers

Rabbu proprietary analytics as of Apr, 27 2026 and Zillow Home Value Index (ZHVI) as of Mar, 17 2026. Revenue projections are estimates based on comparable properties and do not guarantee future performance. Data reflects trailing 12-month historical averages and may not capture very recent market shifts. Local regulations, HOA rules, and tax obligations vary and should be independently verified before making investment decisions.