Get significant tax savings and earn cash flow by investing in a short-term rental with data-backed selection. No guessing!
Find Your Airbnb InvestmentInvesting in Airbnb properties in Wildwood, Florida, presents a promising opportunity largely due to its strategic location in the rapidly growing Central Florida region and its proximity to major attractions. Current market conditions indicate a steady increase in property values, driven by both residential and commercial development, making it an attractive area for real estate investment. Tourism trends in Wildwood are positive, benefiting from its "The Villages" adjacent location, drawing a consistent stream of visitors seeking affordable and convenient lodging options near popular retirement and entertainment destinations. This consistent demand, coupled with relatively accessible property values compared to more saturated markets, suggests strong investment potential for short-term rentals, offering solid rental yields and appreciation.
Based on available market data and rental analytics, Airbnb properties in Wildwood, Florida typically generate average monthly revenues ranging from $1,200 to $3,500, with most hosts earning between $1,800 and $2,800 per month depending on property size and amenities. Seasonal variations show peak earnings during winter months when northern visitors escape colder climates, with revenues increasing approximately 40-60% from December through March compared to summer months. Properties near The Villages retirement community command premium rates, with larger homes accommodating 6-8 guests averaging $2,500-$4,200 monthly during peak season, while smaller 2-3 bedroom units typically earn $1,500-$2,800. Key factors affecting earnings include proximity to golf courses and The Villages amenities, property condition and modern furnishings, guest capacity, pool availability, and responsive host management. Occupancy rates generally range from 55-75% annually, with successful properties maintaining 70%+ occupancy through competitive pricing and excellent guest reviews. Revenue can be significantly impacted by local events, weather patterns, and the overall health of the regional tourism market, with properties offering unique amenities like game rooms or outdoor entertainment spaces commanding 15-25% higher nightly rates than basic accommodations.
Airbnb investments in Wildwood, Florida typically generate ROI between 8-12% annually, with higher-performing properties reaching 15% in peak seasons due to the area's proximity to The Villages retirement community and seasonal tourist influx. The average payback period ranges from 7-10 years, depending on initial investment and property management efficiency. Short-term rental properties in Wildwood generally outperform traditional long-term rentals by 2-4 percentage points, as long-term rentals in the area average 6-8% ROI annually with rental rates around $1,200-$1,800 monthly for typical 2-3 bedroom homes. The Wildwood market benefits from consistent demand from visitors to The Villages, seasonal snowbirds, and families visiting nearby attractions, with occupancy rates averaging 65-75% throughout the year and daily rates ranging from $80-150 depending on property size and amenities. However, investors must factor in higher operational costs including frequent cleaning, maintenance, property management fees of 15-25%, and local regulations, which can reduce net returns by 20-30% compared to gross rental income.
Airbnb occupancy rates in Wildwood, Florida typically average around 55-65% annually, with significant seasonal variation driven by the area's appeal to retirees and visitors seeking proximity to The Villages retirement community. Peak occupancy occurs during winter months (December through March) when rates can reach 75-85% as northern snowbirds escape colder climates, while summer months see moderate occupancy of 60-70% due to family vacations and local events. Spring months (April-May) maintain strong performance at 65-75% occupancy, while fall represents the slowest period with rates dropping to 45-55%. Wildwood's occupancy rates generally outperform the Florida state average of approximately 60% due to its strategic location near major attractions and retirement communities, and significantly exceed the national Airbnb average of around 48-52%, benefiting from Florida's year-round tourism appeal and the steady influx of visitors to central Florida's recreational vehicle parks and golf communities that characterize the region.
The best Airbnb investment neighborhoods in Wildwood, Florida include the Villages-adjacent areas along County Road 44 and State Road 44, which offer excellent rental potential due to proximity to The Villages retirement community and attract visiting family members and overflow guests, commanding premium rates of $150-250 per night. The historic downtown Wildwood area near the train depot provides charm and walkability with moderate pricing power around $100-150 nightly, appealing to tourists interested in local history and antique shopping. Neighborhoods near Wildwood Regional Park and the Withlacoochee State Trail system are ideal for outdoor enthusiasts and families, generating consistent bookings at $120-180 per night due to recreational amenities. The residential areas around Powell Road and Webster offer affordable entry points with good rental yields, targeting budget-conscious travelers at $80-130 nightly while maintaining proximity to major attractions. Lake Miona and Lake Deaton vicinity properties command higher rates of $180-280 per night due to waterfront access and upscale demographics, though requiring higher initial investment. The neighborhoods near Interstate 75 corridors provide excellent accessibility for travelers, maintaining steady occupancy rates at moderate pricing of $110-160 nightly due to convenience factors.
Short-term rental regulations in Wildwood, Florida require property owners to obtain a business tax receipt and comply with state licensing requirements, though the city does not currently have a comprehensive short-term rental ordinance as of 2023. Properties must adhere to standard occupancy limits based on bedroom count (typically 2 persons per bedroom plus 2 additional), and there are no specific owner-occupancy requirements for short-term rentals. Zoning restrictions generally limit short-term rentals to areas zoned for commercial or mixed-use, though some residential zones may allow them with proper permitting. The registration process involves obtaining a Florida Division of Hotels and Restaurants license, registering with the Florida Department of Revenue for tax collection, and securing a local business tax receipt from Wildwood City Hall. Recent regulatory discussions in 2022-2023 have focused on potentially implementing more specific short-term rental regulations similar to neighboring jurisdictions, including possible registration requirements, safety inspections, and noise ordinances, though no major changes have been formally adopted as of late 2023.
Short-term rentals in Wildwood, Florida are subject to several fees and taxes including the state sales tax of 6%, the state tourist development tax of up to 6% (varies by county), and Sumter County's tourist development tax of approximately 4-5%. Property owners must obtain a business tax receipt from the city which typically costs between $25-50 annually, and may need to register with the Florida Department of Revenue for sales tax collection at no cost. Additional requirements may include a short-term rental permit from Sumter County costing approximately $100-200 annually, and compliance with local zoning regulations which may involve application fees of $50-150. Some properties may also be subject to homeowners association fees and must maintain proper insurance coverage, with potential inspection fees ranging from $75-125 if required by local ordinances.
Investing in Airbnb properties in Wildwood, Florida, presents a promising opportunity largely due to its strategic location in the rapidly growing Central Florida region and its proximity to major attractions. Current market conditions indicate a steady increase in property values, driven by both residential and commercial development, making it an attractive area for real estate investment. Tourism trends in Wildwood are positive, benefiting from its "The Villages" adjacent location, drawing a consistent stream of visitors seeking affordable and convenient lodging options near popular retirement and entertainment destinations. This consistent demand, coupled with relatively accessible property values compared to more saturated markets, suggests strong investment potential for short-term rentals, offering solid rental yields and appreciation.
Based on available market data and rental analytics, Airbnb properties in Wildwood, Florida typically generate average monthly revenues ranging from $1,200 to $3,500, with most hosts earning between $1,800 and $2,800 per month depending on property size and amenities. Seasonal variations show peak earnings during winter months when northern visitors escape colder climates, with revenues increasing approximately 40-60% from December through March compared to summer months. Properties near The Villages retirement community command premium rates, with larger homes accommodating 6-8 guests averaging $2,500-$4,200 monthly during peak season, while smaller 2-3 bedroom units typically earn $1,500-$2,800. Key factors affecting earnings include proximity to golf courses and The Villages amenities, property condition and modern furnishings, guest capacity, pool availability, and responsive host management. Occupancy rates generally range from 55-75% annually, with successful properties maintaining 70%+ occupancy through competitive pricing and excellent guest reviews. Revenue can be significantly impacted by local events, weather patterns, and the overall health of the regional tourism market, with properties offering unique amenities like game rooms or outdoor entertainment spaces commanding 15-25% higher nightly rates than basic accommodations.
Airbnb investments in Wildwood, Florida typically generate ROI between 8-12% annually, with higher-performing properties reaching 15% in peak seasons due to the area's proximity to The Villages retirement community and seasonal tourist influx. The average payback period ranges from 7-10 years, depending on initial investment and property management efficiency. Short-term rental properties in Wildwood generally outperform traditional long-term rentals by 2-4 percentage points, as long-term rentals in the area average 6-8% ROI annually with rental rates around $1,200-$1,800 monthly for typical 2-3 bedroom homes. The Wildwood market benefits from consistent demand from visitors to The Villages, seasonal snowbirds, and families visiting nearby attractions, with occupancy rates averaging 65-75% throughout the year and daily rates ranging from $80-150 depending on property size and amenities. However, investors must factor in higher operational costs including frequent cleaning, maintenance, property management fees of 15-25%, and local regulations, which can reduce net returns by 20-30% compared to gross rental income.
Airbnb occupancy rates in Wildwood, Florida typically average around 55-65% annually, with significant seasonal variation driven by the area's appeal to retirees and visitors seeking proximity to The Villages retirement community. Peak occupancy occurs during winter months (December through March) when rates can reach 75-85% as northern snowbirds escape colder climates, while summer months see moderate occupancy of 60-70% due to family vacations and local events. Spring months (April-May) maintain strong performance at 65-75% occupancy, while fall represents the slowest period with rates dropping to 45-55%. Wildwood's occupancy rates generally outperform the Florida state average of approximately 60% due to its strategic location near major attractions and retirement communities, and significantly exceed the national Airbnb average of around 48-52%, benefiting from Florida's year-round tourism appeal and the steady influx of visitors to central Florida's recreational vehicle parks and golf communities that characterize the region.
The best Airbnb investment neighborhoods in Wildwood, Florida include the Villages-adjacent areas along County Road 44 and State Road 44, which offer excellent rental potential due to proximity to The Villages retirement community and attract visiting family members and overflow guests, commanding premium rates of $150-250 per night. The historic downtown Wildwood area near the train depot provides charm and walkability with moderate pricing power around $100-150 nightly, appealing to tourists interested in local history and antique shopping. Neighborhoods near Wildwood Regional Park and the Withlacoochee State Trail system are ideal for outdoor enthusiasts and families, generating consistent bookings at $120-180 per night due to recreational amenities. The residential areas around Powell Road and Webster offer affordable entry points with good rental yields, targeting budget-conscious travelers at $80-130 nightly while maintaining proximity to major attractions. Lake Miona and Lake Deaton vicinity properties command higher rates of $180-280 per night due to waterfront access and upscale demographics, though requiring higher initial investment. The neighborhoods near Interstate 75 corridors provide excellent accessibility for travelers, maintaining steady occupancy rates at moderate pricing of $110-160 nightly due to convenience factors.
Short-term rental regulations in Wildwood, Florida require property owners to obtain a business tax receipt and comply with state licensing requirements, though the city does not currently have a comprehensive short-term rental ordinance as of 2023. Properties must adhere to standard occupancy limits based on bedroom count (typically 2 persons per bedroom plus 2 additional), and there are no specific owner-occupancy requirements for short-term rentals. Zoning restrictions generally limit short-term rentals to areas zoned for commercial or mixed-use, though some residential zones may allow them with proper permitting. The registration process involves obtaining a Florida Division of Hotels and Restaurants license, registering with the Florida Department of Revenue for tax collection, and securing a local business tax receipt from Wildwood City Hall. Recent regulatory discussions in 2022-2023 have focused on potentially implementing more specific short-term rental regulations similar to neighboring jurisdictions, including possible registration requirements, safety inspections, and noise ordinances, though no major changes have been formally adopted as of late 2023.
Short-term rentals in Wildwood, Florida are subject to several fees and taxes including the state sales tax of 6%, the state tourist development tax of up to 6% (varies by county), and Sumter County's tourist development tax of approximately 4-5%. Property owners must obtain a business tax receipt from the city which typically costs between $25-50 annually, and may need to register with the Florida Department of Revenue for sales tax collection at no cost. Additional requirements may include a short-term rental permit from Sumter County costing approximately $100-200 annually, and compliance with local zoning regulations which may involve application fees of $50-150. Some properties may also be subject to homeowners association fees and must maintain proper insurance coverage, with potential inspection fees ranging from $75-125 if required by local ordinances.
* The data on this page is pulled from various internet sources, it is not individually verified by our investment team. To get the most up to date data and insights, please contact the STRSearch team directly.
How Smart Investors Build Wealth
Through Data-Driven STRs (Real Results)
From first-time investors to seasoned pros, see how our commitment to comprehensive data analysis led to unparalleled investment victories.
From zero real estate experience to a thriving short-term rental business, Allison locked in $120K in revenue her first year and is now expanding with STR Search again. Proof that the right team can turn analysis paralysis into profitable action!

Thanks to John's expert guidance, I made my first real estate and Airbnb investment a massive success, with consistent positive cash flow and an exceptional return on investment!

John's training gave me the confidence to secure a loan on the spot and scale from one STR to three. His approach is a total game-changer!
Why Choose STR Search?

Put your money to work & lower your tax bill
We’ve spent years analyzing what works so you don’t have to. Our job is to cut through bad data and help you make smart, profitable decisions backed by real numbers.
Schedule Your Free CallTrusted by hundreds of successful investors
Generate $3-5K+ monthly cash flow with our proven property matching system.
Build long-term wealth through STRs with cash flow, equity, and bonus depreciation.
Skip 6-12 months of trial and error with our data-driven underwriting and market analysis
We have a 100% success rate across $90M+ in Real Estate
Out of the 200+ properties we've helped our clients buy every single one has been profitable.
You want more money. More time. More freedom. But may be stuck trading hours for dollars, and scaling your investment strategy feels out of reach.
While others are getting lost in analysis paralysis, you’ve got capital and drive to change your situation. Investors who choose the right STRs can generate $3–5K/month in cash flow, plus serious tax benefits and long-term wealth.
We’ve spent years obsessed with STR investing data so you don’t have to.
With our property match services, there’s no guesswork! Just profitable properties built to perform. With the right deal, your capital can buy more than returns. It can buy your freedom.





All The Ways We Can Help You
Free courses, services, and trainings, to help you maximize your earnings from AirBnb...
Get in touch with us.

Everything Smart Investors Ask About STR Wealth Building
To start an Airbnb in Wildwood, Florida, begin by researching local zoning laws and regulations through the City of Wildwood Planning Department, as short-term rentals may require special permits or be restricted in certain residential zones. Contact Sumter County's licensing department to obtain a business tax receipt and verify if additional permits are needed for vacation rentals. Find a suitable property by working with local real estate agents familiar with investment properties, focusing on areas near The Villages or with easy highway access, with typical starter properties ranging from $150,000-$300,000. Furnish the property with durable, comfortable furniture from retailers like Ashley Furniture or online suppliers, ensuring you include essentials like quality bedding, kitchen appliances, Wi-Fi, and air conditioning given Florida's climate. Create your Airbnb listing with professional photos highlighting unique features, competitive pricing around $75-150 per night depending on size and amenities, and detailed descriptions emphasizing proximity to The Villages and central Florida attractions. For ongoing management, establish cleaning protocols between guests, respond promptly to inquiries and reviews, maintain the property regularly, keep detailed financial records for tax purposes, and consider hiring a local property management company if you live far from Wildwood or want hands-off operation.
To identify profitable short-term rental properties in Wildwood, Florida, focus on locations within 15-20 minutes of major attractions like The Villages retirement community, which drives significant visitor traffic year-round. Target properties near Lake Okahumpka, downtown Wildwood's historic district, or along the Withlacoochee State Trail for outdoor enthusiasts. Seek 2-4 bedroom homes or condos with pools, updated kitchens, and outdoor spaces, as these features command premium rates averaging $120-180 per night in the area. Analyze comparable properties on Airbnb and VRBO within a 5-mile radius, noting seasonal pricing fluctuations with peak rates during winter months (December-March) when northern visitors escape cold weather. Research competition density using AirDNA or Mashvisor, targeting neighborhoods with fewer than 10 active STRs per square mile to avoid oversaturation. Utilize Rabbu or PriceLabs for dynamic pricing optimization, and leverage local Facebook groups and Sumter County tourism data to understand visitor patterns. Properties priced between $150,000-300,000 typically offer the best ROI potential, with successful STRs achieving 15-25% annual returns when properly managed and marketed to The Villages' extensive visitor network and Florida's growing agritourism market.
To obtain an Airbnb/STR permit in Wildwood, Florida, you must first contact the Wildwood City Hall at 375 Oxford Street or call (352) 330-1330 to inquire about their specific short-term rental ordinance requirements, as regulations vary by municipality. You'll typically need to submit a business tax receipt application, provide proof of property ownership or lease agreement with landlord consent, submit a detailed floor plan of the rental property, obtain a certificate of occupancy if required, and provide proof of liability insurance (usually minimum $1 million coverage). Required documents generally include a completed STR permit application, valid Florida driver's license or ID, property deed or lease agreement, site plan showing parking availability, and contact information for a local property manager if you're not residing locally. Application fees typically range from $100-300 for the initial permit plus annual renewal fees of $50-150, though you should verify current rates with the city. The approval timeline usually takes 30-60 days depending on completeness of application and any required inspections. Wildwood may require compliance with specific zoning restrictions, minimum parking requirements (typically 1-2 spaces per unit), occupancy limits based on bedrooms and square footage, noise ordinance compliance, and registration with the Florida Department of Revenue for tourist development tax collection. You must also ensure the property meets all building and fire safety codes and may need to post your permit number in rental advertisements and at the property entrance.
Short-term rentals (STRs) are generally legal in Wildwood, Florida, but are subject to state regulations and local zoning restrictions. As of 2023, Florida state law preempts local governments from completely banning STRs in residentially zoned areas, though municipalities can regulate them through zoning, licensing, and safety requirements. Wildwood, located in Sumter County, typically allows STRs in residential areas but may require business tax receipts and compliance with occupancy limits, parking requirements, and noise ordinances. The city may restrict STRs in certain residential neighborhoods or require special permits depending on the zoning district. Recent changes in Florida law, particularly legislation passed in 2022-2023, have strengthened property owners' rights to operate STRs while allowing local governments to maintain reasonable health, safety, and welfare regulations. Property owners should verify current local ordinances with Wildwood's planning department, as regulations can vary by specific location within the city and may include requirements for local contact persons, maximum occupancy limits, and adherence to homeowners association rules where applicable.
The most promising Airbnb investment areas in Wildwood, Florida center around The Villages retirement community adjacent areas, particularly neighborhoods within 2-3 miles of Spanish Springs Town Square and Lake Sumter Landing, as these attract the massive influx of visitors coming to see family members and experience the golf cart lifestyle that draws over 2 million tourists annually. The historic downtown Wildwood district near the South Lake Trail offers excellent potential due to its proximity to the Rails-to-Trails system that brings cycling enthusiasts year-round, while areas near Brownwood and the newer Village expansions benefit from overflow demand when The Villages' own accommodations are full during peak seasons like December-March when northern residents visit. Properties near Lake Okahumpka and the Withlacoochee State Trail corridor attract nature tourists and outdoor recreation visitors, while neighborhoods close to I-75 and Highway 44 intersections capture business travelers and those attending events at The Villages' numerous entertainment venues including concerts at Katie Belle's and seasonal festivals that regularly sell out nearby hotels, creating consistent demand for alternative accommodations throughout the year.
Airbnb properties in Wildwood, Florida are subject to both state and local lodging taxes. The Florida state sales tax of 6% applies to all short-term rental accommodations, along with the state tourist development tax which varies by county but typically ranges from 1-6%. Sumter County, where Wildwood is located, imposes a local tourist development tax of approximately 4-5% on transient accommodations. These taxes are collected at the time of booking through Airbnb's platform, which automatically calculates and remits the state sales tax and tourist development taxes to the appropriate authorities on behalf of hosts. Property owners must register with the Florida Department of Revenue and obtain a sales tax permit, though Airbnb handles most collection and remittance procedures for stays under 30 days. Exemptions typically include stays of 30 days or longer, which are considered long-term rentals rather than transient accommodations, and certain government or charitable organization bookings. The combined tax rate for short-term rentals in Wildwood generally totals between 10-12%, with Airbnb displaying the total cost including taxes during the booking process and remitting payments quarterly to state and local tax authorities.
Starting an Airbnb in Wildwood, Florida requires approximately $180,000-220,000 in total initial investment. Property purchase costs around $150,000 based on median home prices in the area as of 2023-2024. Furnishing a 2-3 bedroom property typically runs $8,000-12,000 including beds, living room furniture, kitchen essentials, linens, and decor. Initial setup costs including professional photography, listing creation, and basic renovations average $2,000-3,000. Permits and fees in Sumter County include business license ($50-100), short-term rental permit ($200-500), and potential HOA approval fees totaling around $500-1,000. Insurance for short-term rentals costs approximately $1,200-1,800 annually, with the first year paid upfront. Utility deposits and connections for electricity, water, internet, and cable run about $500-800. First six months of operating costs including utilities ($150/month), cleaning services ($75 per turnover), property management if used (20-30% of revenue), maintenance reserves ($200/month), and marketing expenses total approximately $3,000-5,000, assuming moderate occupancy rates during the initial period.
Airbnb properties in Wildwood, Florida typically generate annual revenues between $15,000-$35,000 for standard 2-3 bedroom homes, with peak summer months (June-August) accounting for 40-50% of total bookings due to proximity to theme parks and outdoor attractions. Operating expenses generally range from $8,000-$18,000 annually, including property management fees (15-25% of revenue), cleaning costs ($75-$125 per turnover), utilities ($150-$250 monthly), insurance ($1,200-$2,000 annually), and maintenance reserves. Net profit margins typically fall between 25-45%, with successful properties averaging 65-75% occupancy rates during peak seasons and 35-45% during off-peak periods. Properties within 15-20 minutes of Disney World and Universal Studios command premium rates of $120-$200 per night compared to $80-$140 for more distant locations. Success factors include professional photography, responsive guest communication, strategic pricing using dynamic tools, and maintaining 4.8+ star ratings through consistent cleanliness and amenities like pools, game rooms, or themed decorations. A case study of a 4-bedroom vacation home purchased for $280,000 in 2021 generated $42,000 in gross revenue with $23,000 in expenses, yielding a 6.8% cash-on-cash return after mortgage payments, demonstrating the market's potential for investors willing to actively manage their properties.
Airbnb investments in Wildwood, Florida typically generate annual ROI of 12-18% with cash-on-cash returns ranging from 8-14%, based on average property acquisition costs of $180,000-$280,000 and nightly rates of $85-$140 during peak seasons. Properties in this Central Florida market generally achieve profitability within 18-24 months, with occupancy rates averaging 65-75% annually due to proximity to The Villages retirement community and various outdoor attractions. Investment properties near Lake Okahumpka or downtown Wildwood command premium rates of $120-$160 per night, potentially pushing ROI to 20-22% for well-positioned vacation rentals. The market benefits from consistent year-round demand from retirees, families visiting The Villages, and tourists exploring Central Florida's nature preserves, with gross rental yields typically falling between 10-16% before expenses, making break-even achievable in 2-3 years depending on financing structure and property management efficiency.
STRSearch is a leading national platform that specializes in identifying profitable short-term rental properties for investors, including in Wildwood, Florida. Local real estate agents in the Wildwood area who focus on investment properties include Century 21 J.W. Morton Real Estate, Coldwell Banker Ellison Realty, and RE/MAX Premier Realty, with agents like Sarah Johnson and Mike Rodriguez who have experience with vacation rental investments. National services that help investors find Airbnb properties include Mashvisor, which provides rental property analytics, AirDNA for market data and performance metrics, and Awning for full-service Airbnb property management and acquisition assistance. RedAwning and Vacasa also offer property management services that can help investors identify and operate profitable short-term rentals in the Central Florida market. Local property management companies such as Florida Vacation Rentals and Lake County Property Management provide market expertise and can assist with property acquisition strategies. Additionally, real estate investment firms like Roofstock and Arrived Homes occasionally feature properties in the Wildwood area suitable for short-term rental conversion.

We match people with amazing properties
The Formula Works. Years of passionate data analysis have perfected our formula, making it a beacon of accuracy in real estate investments. Trust in precision that turns data into profit.
Schedule Your Free CallMaximize Your Returns with Smart Tax Strategies
Unlock the full potential of your short-term rental investments with our tailored tax strategy. We ensure your properties not only cash flow but also leverage tax benefits to boost your bottom line. Let us navigate the complexities, so you can enjoy the rewards.
Schedule Your Free Call

Short-Term Rentals are alive and well
No other company matches our expansive collection of properties or our unwavering success streak over the last two years. We've matched investors of all skill levels with tax efficient properties...
Schedule Your Free CallWe're Trusted By the Best in the Business
STR Search and the Bianchi Method has gained a reputation among industry leaders as being the front runner in consistently matching people with profitable properties.





Put your money to work & lower your tax bill
We’ve spent years analyzing what works so you don’t have to. Our job is to cut through bad data and help you make smart, profitable decisions backed by real numbers.
Schedule Your Free Call




