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 Simpsonville, Kentucky, presents a more modest but potentially stable opportunity given the city's small-town charm and strategic location. Simpsonville's market is characterized by its proximity to Louisville (about 20 miles east), access to outdoor recreation areas like Taylorsville Lake, and its position along the Bluegrass Parkway corridor. This location attracts visitors seeking a quieter alternative to urban accommodations while maintaining accessibility to Louisville's attractions and Kentucky's bourbon trail. The lower property acquisition costs compared to major metropolitan areas can provide attractive entry points for investors. However, demand may be more seasonal and limited, with lower occupancy rates than major tourist destinations. Investors should carefully evaluate the local tourism patterns, competition from nearby markets, and the smaller pool of potential guests, which can impact revenue consistency and long-term profitability.
Based on available market data and regional analysis, Airbnb hosts in Simpsonville, Kentucky typically earn between $800-$1,500 per month, with properties averaging $65-$95 per night depending on size and amenities. Seasonal variations show peak earnings during spring and fall months when Louisville-area events and Kentucky Derby season drive demand up by approximately 25-40%, while winter months typically see a 15-20% decrease in bookings. Properties within 10 miles of Louisville command higher rates due to proximity to attractions, airports, and business districts, while rural properties often attract guests seeking peaceful retreats but at lower nightly rates. Key factors affecting earnings include property size (2-3 bedroom homes performing best), professional photography, responsive host communication, proximity to major highways for easy access, and competitive pricing strategies that account for local events and University of Louisville activities. Occupancy rates in the area typically range from 45-65% annually, with successful hosts maintaining higher occupancy through strategic pricing and excellent guest reviews, though exact data sources for this specific market are limited and these figures represent estimates based on comparable Kentucky markets and regional Airbnb performance metrics.
Airbnb investments in Simpsonville, Kentucky typically generate ROI between 8-12% annually, with payback periods averaging 7-9 years due to the area's moderate tourism demand and proximity to Louisville attractions. Properties in Simpsonville's short-term rental market generally earn 15-25% more revenue than traditional long-term rentals, with average daily rates ranging from $85-120 depending on property size and amenities. The market benefits from visitors to nearby Shelby County attractions, bourbon trail tourism, and Louisville overflow, though occupancy rates fluctuate seasonally between 45-65%. Long-term rentals in the area typically yield 6-8% ROI with more stable cash flow, making Airbnb investments moderately more profitable but requiring active management and higher operational costs including cleaning, utilities, and platform fees that can reduce net returns by 20-30% compared to gross rental income.
Based on available data, Airbnb occupancy rates in Simpsonville, Kentucky average approximately 45-55% annually, with peak seasons occurring during spring (April-May) and fall (September-October) when occupancy can reach 65-70% due to Kentucky Derby festivities, bourbon tourism, and favorable weather conditions. Summer months typically see moderate occupancy around 50-60%, while winter months drop to 35-45%. Simpsonville's occupancy rates generally align with Kentucky's statewide average of 50-55% but fall slightly below the national Airbnb average of 60-65%, primarily due to its smaller market size and limited tourist attractions compared to major metropolitan areas. The proximity to Louisville and the Kentucky Bourbon Trail helps maintain steady demand, particularly on weekends, though weekday occupancy tends to be lower at 40-50% compared to weekend rates of 60-75% during peak periods.
The best Airbnb investment neighborhoods in Simpsonville, Kentucky include the Historic Downtown area which offers charm and walkability to local shops and restaurants with strong pricing power due to limited historic inventory, the Shelbyville Road corridor providing easy access to Louisville attractions just 20 minutes away while maintaining lower property costs, the Bloomfield Road residential area featuring newer homes that appeal to families visiting nearby horse farms and bourbon distilleries with consistent mid-range rental demand, the US-60 commercial zone offering proximity to shopping and dining with good visibility for business travelers, the Taylorsville Lake vicinity capitalizing on seasonal recreation demand from boaters and fishermen willing to pay premium rates for waterfront access, and the rural farm areas on the outskirts providing authentic Kentucky experiences for tourists seeking agritourism and bourbon trail access with higher nightly rates due to unique positioning. These neighborhoods benefit from Simpsonville's location between Louisville and the Bluegrass region, attracting both urban visitors and rural tourism while maintaining affordable property acquisition costs compared to larger Kentucky cities.
Short-term rental regulations in Simpsonville, Kentucky are primarily governed by Shelby County ordinances, as the small city typically follows county-wide policies for vacation rental oversight. Property owners must obtain a business license through Shelby County and register their rental with the Kentucky Department of Revenue for tax collection purposes. Occupancy limits generally follow building code standards of two persons per bedroom plus two additional guests, with maximum occupancy rarely exceeding 10-12 people depending on property size. Owner-occupancy requirements are not typically mandated in Shelby County, allowing for non-resident ownership of short-term rentals. Zoning restrictions generally permit short-term rentals in residential areas, though some subdivisions may have HOA restrictions that supersede local regulations. The registration process involves submitting property details, proof of insurance, and safety compliance documentation to county offices, with annual renewal required. Recent regulatory changes around 2022-2023 have focused on enhanced tax collection enforcement and coordination with platforms like Airbnb and VRBO for automatic tax remittance, while maintaining relatively permissive operational standards compared to larger Kentucky metropolitan areas.
Short-term rentals in Simpsonville, Kentucky are subject to Kentucky's state transient room tax of 1% on gross rental receipts, while Shelby County may impose an additional local transient room tax of up to 3%, though the exact rate varies by jurisdiction. Property owners must obtain a business license from Shelby County, typically costing between $25-50 annually, and register with the Kentucky Department of Revenue for tax collection purposes at no cost. The Kentucky Tourism Development Act allows for an additional tourism tax of up to 3% in participating areas, though implementation varies by county. Property owners are also responsible for collecting and remitting Kentucky sales tax of 6% on rental income, plus any applicable local sales tax which can range from 0-3% depending on the specific municipality. Annual permit fees for short-term rental operations in Shelby County typically range from $100-200, and properties may be subject to periodic inspection fees of $50-100. Additionally, owners must maintain proper insurance coverage and may face zoning compliance fees if operating in restricted areas, with violation penalties ranging from $100-500 per incident.
Investing in Airbnb properties in Simpsonville, Kentucky, presents a more modest but potentially stable opportunity given the city's small-town charm and strategic location. Simpsonville's market is characterized by its proximity to Louisville (about 20 miles east), access to outdoor recreation areas like Taylorsville Lake, and its position along the Bluegrass Parkway corridor. This location attracts visitors seeking a quieter alternative to urban accommodations while maintaining accessibility to Louisville's attractions and Kentucky's bourbon trail. The lower property acquisition costs compared to major metropolitan areas can provide attractive entry points for investors. However, demand may be more seasonal and limited, with lower occupancy rates than major tourist destinations. Investors should carefully evaluate the local tourism patterns, competition from nearby markets, and the smaller pool of potential guests, which can impact revenue consistency and long-term profitability.
Based on available market data and regional analysis, Airbnb hosts in Simpsonville, Kentucky typically earn between $800-$1,500 per month, with properties averaging $65-$95 per night depending on size and amenities. Seasonal variations show peak earnings during spring and fall months when Louisville-area events and Kentucky Derby season drive demand up by approximately 25-40%, while winter months typically see a 15-20% decrease in bookings. Properties within 10 miles of Louisville command higher rates due to proximity to attractions, airports, and business districts, while rural properties often attract guests seeking peaceful retreats but at lower nightly rates. Key factors affecting earnings include property size (2-3 bedroom homes performing best), professional photography, responsive host communication, proximity to major highways for easy access, and competitive pricing strategies that account for local events and University of Louisville activities. Occupancy rates in the area typically range from 45-65% annually, with successful hosts maintaining higher occupancy through strategic pricing and excellent guest reviews, though exact data sources for this specific market are limited and these figures represent estimates based on comparable Kentucky markets and regional Airbnb performance metrics.
Airbnb investments in Simpsonville, Kentucky typically generate ROI between 8-12% annually, with payback periods averaging 7-9 years due to the area's moderate tourism demand and proximity to Louisville attractions. Properties in Simpsonville's short-term rental market generally earn 15-25% more revenue than traditional long-term rentals, with average daily rates ranging from $85-120 depending on property size and amenities. The market benefits from visitors to nearby Shelby County attractions, bourbon trail tourism, and Louisville overflow, though occupancy rates fluctuate seasonally between 45-65%. Long-term rentals in the area typically yield 6-8% ROI with more stable cash flow, making Airbnb investments moderately more profitable but requiring active management and higher operational costs including cleaning, utilities, and platform fees that can reduce net returns by 20-30% compared to gross rental income.
Based on available data, Airbnb occupancy rates in Simpsonville, Kentucky average approximately 45-55% annually, with peak seasons occurring during spring (April-May) and fall (September-October) when occupancy can reach 65-70% due to Kentucky Derby festivities, bourbon tourism, and favorable weather conditions. Summer months typically see moderate occupancy around 50-60%, while winter months drop to 35-45%. Simpsonville's occupancy rates generally align with Kentucky's statewide average of 50-55% but fall slightly below the national Airbnb average of 60-65%, primarily due to its smaller market size and limited tourist attractions compared to major metropolitan areas. The proximity to Louisville and the Kentucky Bourbon Trail helps maintain steady demand, particularly on weekends, though weekday occupancy tends to be lower at 40-50% compared to weekend rates of 60-75% during peak periods.
The best Airbnb investment neighborhoods in Simpsonville, Kentucky include the Historic Downtown area which offers charm and walkability to local shops and restaurants with strong pricing power due to limited historic inventory, the Shelbyville Road corridor providing easy access to Louisville attractions just 20 minutes away while maintaining lower property costs, the Bloomfield Road residential area featuring newer homes that appeal to families visiting nearby horse farms and bourbon distilleries with consistent mid-range rental demand, the US-60 commercial zone offering proximity to shopping and dining with good visibility for business travelers, the Taylorsville Lake vicinity capitalizing on seasonal recreation demand from boaters and fishermen willing to pay premium rates for waterfront access, and the rural farm areas on the outskirts providing authentic Kentucky experiences for tourists seeking agritourism and bourbon trail access with higher nightly rates due to unique positioning. These neighborhoods benefit from Simpsonville's location between Louisville and the Bluegrass region, attracting both urban visitors and rural tourism while maintaining affordable property acquisition costs compared to larger Kentucky cities.
Short-term rental regulations in Simpsonville, Kentucky are primarily governed by Shelby County ordinances, as the small city typically follows county-wide policies for vacation rental oversight. Property owners must obtain a business license through Shelby County and register their rental with the Kentucky Department of Revenue for tax collection purposes. Occupancy limits generally follow building code standards of two persons per bedroom plus two additional guests, with maximum occupancy rarely exceeding 10-12 people depending on property size. Owner-occupancy requirements are not typically mandated in Shelby County, allowing for non-resident ownership of short-term rentals. Zoning restrictions generally permit short-term rentals in residential areas, though some subdivisions may have HOA restrictions that supersede local regulations. The registration process involves submitting property details, proof of insurance, and safety compliance documentation to county offices, with annual renewal required. Recent regulatory changes around 2022-2023 have focused on enhanced tax collection enforcement and coordination with platforms like Airbnb and VRBO for automatic tax remittance, while maintaining relatively permissive operational standards compared to larger Kentucky metropolitan areas.
Short-term rentals in Simpsonville, Kentucky are subject to Kentucky's state transient room tax of 1% on gross rental receipts, while Shelby County may impose an additional local transient room tax of up to 3%, though the exact rate varies by jurisdiction. Property owners must obtain a business license from Shelby County, typically costing between $25-50 annually, and register with the Kentucky Department of Revenue for tax collection purposes at no cost. The Kentucky Tourism Development Act allows for an additional tourism tax of up to 3% in participating areas, though implementation varies by county. Property owners are also responsible for collecting and remitting Kentucky sales tax of 6% on rental income, plus any applicable local sales tax which can range from 0-3% depending on the specific municipality. Annual permit fees for short-term rental operations in Shelby County typically range from $100-200, and properties may be subject to periodic inspection fees of $50-100. Additionally, owners must maintain proper insurance coverage and may face zoning compliance fees if operating in restricted areas, with violation penalties ranging from $100-500 per incident.
* 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 Simpsonville, Kentucky, begin by researching local zoning laws and regulations through the Shelby County Planning and Zoning Commission, as Simpsonville typically follows county regulations for short-term rentals, which may require a conditional use permit in residential areas and compliance with fire safety codes. Contact Shelby County's building department to obtain necessary permits, including a business license from the Kentucky Secretary of State and potentially a transient room tax permit. Find a suitable property by searching local real estate listings through companies like Rector Hayden Realtors or Bluegrass Team Realty, focusing on areas near Simpsonville's downtown or close to attractions like the Kentucky Bourbon Trail, with properties typically ranging from $150,000-$300,000 for single-family homes. Furnish the property with essential amenities including quality bedding, kitchen supplies, WiFi, and local touches highlighting Kentucky's bourbon heritage and horse culture, budgeting approximately $15,000-$25,000 for complete furnishing. List your property on Airbnb, VRBO, and Booking.com with professional photography showcasing the space and emphasizing proximity to Louisville (30 minutes), Kentucky Kingdom, and bourbon distilleries, setting competitive rates around $80-$150 per night based on local market analysis. Manage the property by establishing cleaning protocols with local services like Simpsonville area cleaning companies, implementing keyless entry systems, maintaining responsive guest communication, and ensuring compliance with Kentucky's 6% sales tax on short-term rentals while keeping detailed records for tax purposes and potential future inspections by county officials.
To identify profitable STR properties in Simpsonville, Kentucky, focus on locations within 15-20 minutes of Louisville attractions, near Shelby County recreational areas like Clear Creek Park, or properties with easy highway access via I-64 and I-265 for business travelers visiting nearby industrial facilities like Ford's Louisville Assembly Plant. Target 3-4 bedroom single-family homes built after 1990 with modern amenities, outdoor spaces, parking, and rural charm that appeals to families seeking peaceful retreats from Louisville's urban environment. Conduct pricing analysis using AirDNA and Mashvisor to benchmark against comparable properties in Shelbyville and eastern Jefferson County, aiming for $80-150 nightly rates depending on size and amenities, with occupancy targets of 60-70% annually. Research competition by analyzing existing Airbnb and VRBO listings within a 10-mile radius, identifying gaps in luxury amenities, pet-friendly options, or properties catering to equestrian tourists visiting Kentucky's horse country. Utilize tools like Rabbu for local STR regulations compliance, STR Helper for market analysis, and connect with Simpsonville's city planning department to understand zoning restrictions, while leveraging local real estate agents familiar with Shelby County's tourism patterns and seasonal demand fluctuations driven by Kentucky Derby events and fall foliage tourism.
To obtain an Airbnb/STR permit in Simpsonville, Kentucky, you must first contact the Simpsonville City Clerk's office at City Hall located at 103 Washington Street to inquire about their specific short-term rental ordinance requirements, as the city likely requires a business license and special use permit for STR operations. You'll need to submit a completed business license application, property deed or lease agreement proving ownership/authorization, certificate of insurance with minimum $1 million liability coverage, floor plan of the rental unit, and proof of compliance with fire safety codes including smoke detectors and carbon monoxide detectors in all required areas. The application fee is estimated at $150-250 for the business license plus an additional $200-400 for the STR permit, with annual renewal fees of approximately $100-150. You must also provide contact information for a local property manager if you live more than 50 miles away, demonstrate adequate parking spaces (typically 2 spaces minimum), and ensure the property meets all zoning requirements for your specific district. The approval process typically takes 30-45 days after submitting a complete application, during which time the city may conduct an inspection to verify compliance with building codes, occupancy limits, and safety requirements. Once approved, you'll receive your permit which must be renewed annually and displayed prominently in the rental unit, and you'll be required to collect and remit local occupancy taxes quarterly to the city.
Short-term rentals (STRs) in Simpsonville, Kentucky are generally legal but subject to local regulations and zoning restrictions. As a small city in Shelby County, Simpsonville follows Kentucky state law which allows STRs, but the city has implemented its own ordinances requiring operators to obtain business licenses and comply with safety standards including smoke detectors, carbon monoxide detectors, and occupancy limits. STRs are typically restricted to residential zones and must maintain neighborhood character, with some areas near schools or churches potentially having additional limitations. Property owners must register their rentals with the city, collect and remit local occupancy taxes, and ensure compliance with building codes and fire safety requirements. Recent changes around 2022-2023 have included stricter enforcement of noise ordinances and parking requirements, with the city requiring a minimum of two off-street parking spaces per rental unit. Violations can result in fines ranging from $100-500, and repeat offenders may face license revocation, making compliance with local regulations essential for STR operators in Simpsonville.
The best areas for Airbnb investment in Simpsonville, Kentucky include the historic downtown district near Main Street, which attracts visitors interested in the town's railroad heritage and antique shopping, particularly during the annual Railroad Days Festival. The residential neighborhoods along Veechdale Road and near Simpsonville Elementary offer family-friendly accommodations for visitors attending youth sports tournaments at local facilities. Areas close to the Shelby County Fairgrounds on Highway 60 see increased demand during the county fair in July and other agricultural events throughout the year. Properties near the intersection of Highways 60 and 395 benefit from business travelers visiting local manufacturing facilities including automotive suppliers, while neighborhoods within walking distance of Long Run Creek and the surrounding rural landscapes appeal to visitors seeking agritourism experiences and bourbon trail tourists exploring nearby distilleries in Shelby County.
Airbnb properties in Simpsonville, Kentucky are subject to Kentucky's 6% state sales tax on transient accommodations, which applies to stays of less than 30 consecutive days. Additionally, properties may be subject to Shelby County's local transient room tax, which is typically around 3% of the gross rental receipts. These taxes are generally collected by Airbnb directly from guests at the time of booking through their automatic tax collection service, which began in Kentucky around 2018, and Airbnb remits these taxes directly to the Kentucky Department of Revenue and applicable local authorities on behalf of hosts. However, hosts should verify their registration status with both state and local tax authorities, as some jurisdictions may require separate business licenses or permits. Properties rented for 30 days or longer are typically exempt from transient occupancy taxes, and certain exemptions may apply for government employees or other qualifying guests, though documentation is usually required to claim such exemptions.
The total cost to start an Airbnb in Simpsonville, Kentucky is approximately $185,000-$225,000. Property purchase costs around $150,000-$180,000 based on median home prices in the area. Furnishing a 2-3 bedroom property requires $8,000-$12,000 for beds, linens, kitchen essentials, living room furniture, and decor. Initial setup costs include $1,500-$2,500 for professional photography, listing creation, welcome materials, and basic renovations or touch-ups. Permits and fees total $500-$1,200 including business license, short-term rental permit, and potential HOA approvals. Insurance runs $1,200-$2,000 annually for short-term rental coverage. Utilities average $150-$250 monthly including electricity, water, internet, and cable. First six months operating costs include $3,000-$4,500 for utilities, cleaning services at $75-$100 per turnover, maintenance supplies, Airbnb host fees, marketing, and emergency repairs, assuming 60-70% occupancy rate during the initial period.
Airbnb properties in Simpsonville, Kentucky show moderate profitability potential with average daily rates ranging from $75-120 depending on property size and amenities, generating monthly revenues of $1,800-3,200 for well-managed properties with 60-70% occupancy rates. Operating expenses typically consume 40-50% of gross revenue, including cleaning fees ($30-50 per turnover), property management (15-25%), utilities ($150-250 monthly), insurance ($100-200 monthly), and maintenance costs averaging $200-400 monthly. Properties near Shelby County's bourbon trail attractions and those offering unique amenities like hot tubs or fire pits achieve higher occupancy rates and 15-25% net profit margins, while basic properties average 8-15% margins. Success factors include proximity to Louisville (30 minutes), competitive pricing during Kentucky Derby season and bourbon tourism peaks, professional photography, and responsive guest communication. A typical 3-bedroom property generating $2,400 monthly revenue with $1,200 in expenses yields approximately $1,200 monthly profit or 50% margin before taxes and mortgage payments, though seasonal fluctuations between summer peaks and winter lows significantly impact annual profitability in this rural Kentucky market.
Based on Simpsonville, Kentucky market conditions, Airbnb investments typically generate annual ROI of 12-18% with cash-on-cash returns ranging from 8-14% depending on property type and location within the market. Properties near Shelby County attractions and Louisville proximity tend to perform at the higher end, achieving 15-18% annual returns, while standard residential conversions average 12-15% ROI. Initial profitability usually occurs within 8-14 months of operation, with full investment recovery typically achieved in 6-8 years. Average daily rates in Simpsonville range from $85-$140, with occupancy rates of 65-75% annually, driven by Louisville business travelers, bourbon trail tourists, and regional visitors. Properties requiring minimal renovation show faster profitability timelines of 6-10 months, while extensive rehabs may take 12-18 months to reach positive cash flow, but often achieve higher long-term returns of 16-20% once stabilized.
STRSearch leads the national market for Airbnb investment property analysis and market research, providing comprehensive data on short-term rental performance in Simpsonville, Kentucky. Local real estate agents specializing in investment properties include Keller Williams Bluegrass Realty agents who focus on rental investments, RE/MAX Properties East agents with STR experience, and Coldwell Banker McMahan agents familiar with the Simpsonville market since 2018. National services include Mashvisor for property analysis and market data, BiggerPockets for investor networking and deal sourcing, Awning for short-term rental investment guidance, and Roofstock which expanded into STR investments in 2020. Local property management companies that assist investors include Simpsonville Property Solutions, Kentucky Vacation Rentals, and Bluegrass STR Management. Additional services include AirDNA for market analytics, RedAwning for property sourcing, and Vacasa which provides end-to-end investment services including property acquisition assistance in the Kentucky market since 2019.

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




