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

Winter Garden Short-Term Rental Market Overview

Winter Garden, FL sits in the heart of the greater Orlando corridor, giving short-term rental operators access to one of the country's most visited tourism regions. With 107 active Airbnb listings, a 55% occupancy rate that edges just above the Florida state average, and an average annual revenue of $19,537, the market is accessible but competitive. Home values averaging $791,181 mean the revenue-to-price ratio requires careful deal sourcing, though strong seasonal peaks—particularly in March—can meaningfully boost annual returns for well-positioned properties.

Key Market Statistics

According to Rabbu market data, the Winter Garden 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 Garden

Winter Garden appeals to investors seeking exposure to the Orlando tourism ecosystem at a slightly quieter entry point than the main resort corridors, though elevated home prices demand disciplined underwriting.

Expert Market Assessment

"Winter Garden presents a competitive opportunity rather than an easy layup—strong tourism demand exists, but elevated home values and rapid supply growth mean margins can be thin without the right property. Seasonality is pronounced: March stands out at $2,544 in average monthly revenue while September dips to just $1,017, so cash reserves for slower months are essential. Two-bedroom properties appear to hit the sweet spot between occupancy and rate, and investors who layer in amenities like pools and outdoor spaces (already prevalent in 66–79% of listings) will be better positioned to capture bookings in an increasingly crowded field."

— Rabbu Market Analysis Team

Key Airbnb Metrics & Trends in Winter Garden

Average revenue by month in Winter Garden

Revenue in Winter Garden peaks sharply in March at $2,544 and drops to its low point in September at $1,017—a spread of over $1,500 that underscores significant seasonality tied to spring tourism and holiday travel. December ($1,896) and February ($1,828) form a secondary high season, while the late-summer months consistently underperform.

Active Airbnb listings by property size in Winter Garden

Supply is nearly evenly split between 2-bedroom (39 listings) and 3-bedroom (40 listings) properties, which together account for about 74% of all active listings. The 1-bedroom segment has just 20 listings, potentially signaling either lower demand for smaller units or a less saturated niche for investors targeting couples and solo travelers.

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

ADR climbs from $86 for 1-bedroom units to $131 for 2-bedrooms, but interestingly dips slightly to $128 for 3-bedroom properties, suggesting that the premium guests will pay doesn't scale linearly with size in this market. The 2-bedroom tier appears to capture the strongest rate positioning relative to its size category.

Average RevPAN by property size in Winter Garden

Two-bedroom properties deliver the highest RevPAN at $76, outpacing both 1-bedrooms ($48) and 3-bedrooms ($63) by a meaningful margin. This makes the 2-bedroom configuration the most efficient revenue generator on a per-available-night basis, driven by a combination of solid ADR and the highest occupancy rate in the market.

Average occupancy rates by property size in Winter Garden

Occupancy is strongest for 2-bedroom listings at 58%, followed closely by 1-bedrooms at 56%, while 3-bedroom properties trail noticeably at 49%. The lower fill rate for larger units suggests that while they command decent nightly rates, demand may not consistently support them—an important cash-flow consideration for investors eyeing bigger properties.

Average monthly revenue by property size in Winter Garden

Three-bedroom properties lead monthly revenue at $1,847, edging out 2-bedrooms at $1,725, while 1-bedroom units generate $1,256. Despite their lower occupancy, 3-bedrooms earn more in absolute dollars per month thanks to their higher nightly rates, though the gap narrows considerably when factoring in the additional acquisition and maintenance costs of larger homes.

Average annual revenue by property size in Winter Garden

On an annual basis, 3-bedroom properties top out at $22,170 and 2-bedrooms at $20,702, while 1-bedrooms generate $15,072. Given that 2-bedrooms achieve nearly the same annual revenue as 3-bedrooms with significantly better occupancy stability, they may offer the strongest return potential when acquisition costs are factored in.

Most common amenities for Airbnb listings in Winter Garden

Parking is universal at 100% of listings, and kitchen access (95%), washer (90%), and self check-in (88%) are near-standard—any listing missing these basics will be at a competitive disadvantage. Outdoor amenities are notably prevalent, with pools at 66% and backyards at 79%, signaling that guests in Winter Garden expect a resort-like home experience, making these features important differentiators rather than luxuries.

Understanding Winter Garden's ROI Score: 50/100

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 Garden's ROI Score of 50 out of 100 places it in the "Competitive Opportunity" band, reflecting a market where demand is real but returns require more intentional strategy. The below-average revenue-to-price ratio—driven by home values near $791K against roughly $19.5K in annual revenue—is the primary drag, while average marks for occupancy stability, market growth, and supply/demand balance suggest a functional but not exceptional operating environment. Pairing this data with thorough local regulatory research and careful property selection will be critical for investors looking to make the numbers work here.

Short-Term Rental Regulations in Winter Garden

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

Permit Requirements

Winter Garden, Florida may require short-term rental operators to obtain a local business tax receipt or STR registration, and the state of Florida mandates a vacation rental license through the Department of Business and Professional Regulation. Investors should verify current permit requirements directly with the City of Winter Garden and the state before listing a property.

Key Restrictions

Common restrictions in Florida STR markets include occupancy limits, minimum-stay requirements, noise and parking regulations, and potential HOA covenants that may prohibit or limit short-term rentals. Some municipalities also impose caps on the number of permits issued, so confirming availability early in the acquisition process is advisable.

Tax Obligations

Short-term rental hosts in Florida are typically responsible for collecting and remitting state sales tax, county tourist development tax, and any applicable local surcharges. Platforms like Airbnb often handle a portion of this collection automatically, but operators should confirm compliance with Orange County and Florida Department of Revenue guidelines.

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

Future Outlook & Long-Term Forecast

"Over the next 12–18 months, expect continued demand driven by Winter Garden's proximity to Orlando's theme parks and attractions, though the 135% year-over-year listing growth signals that supply is expanding rapidly. Occupancy is likely to hover in the 53–57% range, with ADR potentially seeing modest increases of 1–3% if hosts differentiate through amenities and guest experience. Peak season around March should continue to outperform, while September remains the softest month—investors should budget for revenue swings of roughly $1,000–$1,500 between peak and trough months."

— Rabbu Market Analysis Team

Frequently asked questions about Airbnb in Winter Garden, FL

What is the average Airbnb occupancy rate in Winter Garden?

The average Airbnb occupancy rate in Winter Garden is currently 55%, which is slightly above the Florida state average of 54%. Occupancy varies by property size, with 2-bedroom units leading at 58% and 3-bedroom properties trailing at 49%. These figures reflect current market conditions and individual results will depend on factors like pricing strategy, listing quality, and seasonal demand.

How much do Airbnb hosts make in Winter Garden?

Airbnb hosts in Winter Garden earn an average of $1,628 per month and approximately $19,537 per year based on trailing 12-month booking data. Revenue varies significantly by property size—3-bedroom listings average $22,170 annually while 1-bedroom units come in around $15,072. Seasonality also plays a major role, with March generating the highest average revenue at $2,544 and September the lowest at $1,017.

Is Winter Garden a good market for Airbnb investment?

Winter Garden carries a Rabbu ROI Score of 50 out of 100, placing it in the "Competitive Opportunity" category. The market benefits from proximity to Orlando's tourism infrastructure and maintains occupancy above the state average, but elevated home values (averaging $791,181) create a below-average revenue-to-price ratio. Success here typically requires selective deal sourcing—finding properties priced below the market average or ones that can command premium nightly rates through amenities and location.

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

The average daily rate for Airbnb listings in Winter Garden is $128, which is well below the Florida state average of $498. ADR varies by property size: 1-bedroom units average $86, 2-bedrooms come in at $131, and 3-bedrooms average $128. The relatively modest ADR reflects the suburban, residential character of the market compared to Florida's beachfront or resort-heavy destinations.

Are short-term rentals legal in Winter Garden?

Short-term rentals operate in Winter Garden, FL, and the state of Florida requires a vacation rental license through the Department of Business and Professional Regulation. Local regulations may also apply, including business tax receipts or specific STR permits from the City of Winter Garden. Investors should consult with local authorities and review any HOA restrictions before purchasing a property intended for short-term rental use.

When is peak season for Airbnb in Winter Garden?

Peak season for Airbnb in Winter Garden centers on March, when average monthly revenue reaches $2,544—nearly 60% above the annual monthly average. December ($1,896) and February ($1,828) are also strong months. The slowest period falls in late summer and early fall, with September bottoming out at $1,017. This pattern aligns with spring break tourism and holiday travel to the greater Orlando area.

How many Airbnbs are there in Winter Garden?

There are currently 107 active Airbnb listings in Winter Garden as of April 2026. The market has seen significant growth, with a 135% year-over-year increase in active listings. Supply is concentrated in 2-bedroom (39 listings) and 3-bedroom (40 listings) properties, with 1-bedroom units making up a smaller share at 20 listings.

How is Airbnb revenue calculated in Winter Garden?

The annual and monthly revenue figures for Winter Garden 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 performance data, the figures naturally reflect seasonal peaks (like March at $2,544) and slower months (like September at $1,017). Individual results can vary meaningfully based on property quality, pricing strategy, and operational management.

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 the Winter Garden market
• Average daily rates, occupancy rates, and RevPAN trends across property sizes
• Monthly and annual revenue metrics based on trailing 12-month booking performance
• Home value data sourced from the Zillow Home Value Index (ZHVI)
• Amenity prevalence data across active listings to benchmark competitive standards

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 averages and current snapshots as of the dates noted; market conditions can shift due to regulatory changes, economic factors, or seasonal variation. Individual property results will vary based on location, condition, pricing strategy, and management quality.