Is Stock Island, Florida Good for Airbnb Investment?

To start an Airbnb in Stock Island, Florida, begin by researching Monroe County's short-term rental regulations, which require a Transient Rental License and compliance with the county's 30% cap on short-term rentals in residential areas, with applications typically costing $500-1,000 annually. Obtain necessary permits including a business tax receipt from Monroe County ($50-150), ensure the property meets fire safety codes with smoke detectors and fire extinguishers, and verify zoning compliance as Stock Island has mixed residential and commercial zones. Find a suitable property by purchasing or securing a long-term lease agreement that explicitly allows short-term rentals, focusing on areas near the marina or Key West attractions, with properties typically ranging $300,000-800,000 for purchase or $2,000-4,000 monthly for rental. Furnish the space with coastal-themed, durable furniture including hurricane-rated windows, quality linens, full kitchen amenities, and outdoor furniture suitable for the tropical climate, budgeting $15,000-30,000 for a complete setup. List your property on Airbnb, VRBO, and Booking.com with professional photography highlighting water views and proximity to Key West (just 4 miles away), setting competitive rates of $150-400 per night depending on season and property size. Manage the property by establishing relationships with local cleaning services ($75-150 per turnover), maintenance contractors familiar with saltwater corrosion issues, and consider hiring a property management company (15-25% of revenue) due to Stock Island's remote location, while maintaining 24/7 guest communication and ensuring compliance with Monroe County's noise ordinances and parking restrictions.

To identify profitable short-term rental properties in Stock Island, Florida, focus on waterfront or water-view locations within walking distance to Key West attractions, as proximity to Mallory Square, Duval Street, and fishing charters drives demand. Target 2-4 bedroom properties with outdoor spaces, pools, boat slips or dock access, and parking, as these features command premium rates averaging $200-400 per night during peak season (December-April). Analyze pricing by comparing similar properties on Airbnb and VRBO within a 2-mile radius, noting that waterfront units typically achieve 70-85% occupancy rates while inland properties see 60-75%. Research competition by monitoring the 200+ existing STR listings in the Stock Island/Key West area, identifying gaps in amenities or underpriced properties, and studying seasonal pricing patterns where winter rates can be 40-60% higher than summer. Utilize tools like AirDNA for market analytics, Mashvisor for investment analysis, and the Monroe County STR permit database to verify legal compliance, while partnering with local property managers familiar with hurricane preparedness requirements and the area's unique zoning restrictions that limit new STR permits, making existing permitted properties particularly valuable.

To obtain an Airbnb/STR permit in Stock Island, Florida, you must apply through Monroe County's Planning and Environmental Resources Department since Stock Island falls under Monroe County jurisdiction. Begin by submitting a Transient Rental License application online through the Monroe County website or in person at 2798 Overseas Highway, Marathon, FL 33050. Required documents include a completed application form, property deed or lease agreement, floor plan showing maximum occupancy, proof of liability insurance ($500,000 minimum), septic system inspection certificate, fire safety inspection, parking plan showing required spaces, and a $500 application fee plus $200 annual renewal fee. The property must comply with Monroe County's density restrictions (limited number of STR permits per area), parking requirements (one space per bedroom), septic capacity verification, and building code compliance. Submit your application with all documents and fees, schedule required inspections with the fire department and building department, await review which typically takes 60-90 days, address any deficiencies identified during review, and once approved, pay the annual license fee and display your permit number in all rental advertisements. The total timeline from application to approval averages 3-4 months, and permits must be renewed annually by December 31st with continued compliance verification.

Short-term rentals (STRs) in Stock Island, Florida are generally legal but subject to Monroe County regulations and restrictions. As of recent years, Monroe County has implemented stricter controls on vacation rentals, requiring proper licensing, registration, and compliance with zoning requirements. Stock Island, being part of unincorporated Monroe County near Key West, falls under county jurisdiction rather than municipal control. The area allows STRs in certain zoning districts but prohibits them in others, particularly in residential neighborhoods designated for long-term housing. Property owners must obtain vacation rental licenses, pay transient occupancy taxes, meet safety requirements including fire safety inspections, and comply with parking and occupancy limits. Recent legal changes around 2018-2020 included caps on new vacation rental permits in some areas of Monroe County to address housing shortages and community concerns, though existing legal rentals were generally grandfathered in. Stock Island specifically has seen increased scrutiny due to its proximity to Key West and pressure on local housing stock, with the county prioritizing workforce housing over tourist accommodations in certain zones.

Stock Island offers several promising areas for Airbnb investment, with the Oceanside Marina district being particularly attractive due to its proximity to luxury yacht charters and fishing tournaments that draw affluent visitors year-round. The Safe Harbor area near the working waterfront appeals to business travelers and contractors working at the naval air station and local marine industries, while also attracting fishing enthusiasts during peak seasons from December through April. The residential neighborhoods along 5th Avenue and Cross Street provide excellent opportunities for family-oriented rentals, benefiting from Stock Island's position as a more affordable alternative to Key West while still offering easy access to Duval Street and major attractions via the short drive or bike ride across Cow Key Bridge. The area near the Stock Island Marina Village has seen significant development and attracts visitors seeking upscale accommodations with marina access, particularly during events like the Key West Race Week and various fishing tournaments hosted at the facility throughout the year.

Stock Island, Florida Airbnb properties are subject to multiple lodging taxes including the Florida state tourist development tax at 6% on the first $3,000 of rent per month, Monroe County's 5% tourist development tax, and the City of Key West's 3% resort tax since Stock Island falls within Key West's jurisdiction as of 2019. These taxes totaling 14% are typically collected by Airbnb directly from guests at the time of booking through their automated tax collection system implemented in 2018, with Airbnb remitting payments monthly to the appropriate tax authorities including the Florida Department of Revenue, Monroe County Tourist Development Council, and Key West city offices. Property owners must register with each taxing authority and may need to file monthly returns even when Airbnb collects taxes, with exemptions generally limited to stays exceeding 30 consecutive days which are considered long-term rentals rather than transient accommodations, though hosts remain responsible for ensuring compliance and may need to collect and remit taxes directly if Airbnb's system doesn't capture all applicable local taxes.

The total cost to start an Airbnb in Stock Island, Florida is approximately $485,000-$565,000. Property purchase costs around $400,000-$450,000 based on median home prices in the area. Furnishing a 2-3 bedroom property requires $15,000-$25,000 for quality furniture, appliances, linens, and decor suitable for vacation rentals. Initial setup costs including professional photography, listing creation, and marketing materials total $2,000-$3,000. Permits and fees including business license, vacation rental permit, and inspection fees range from $1,500-$2,500 depending on Monroe County requirements. Insurance for short-term rentals costs $3,000-$4,000 annually, with the first year paid upfront. Utility deposits and setup fees for electricity, water, internet, and cable total approximately $1,000-$1,500. First six months operating costs including utilities ($1,800), cleaning services ($3,600), maintenance and repairs ($2,000), property management software ($600), and marketing ($1,000) total around $9,000. Additional considerations include potential HOA fees, property taxes, and emergency fund reserves which could add another $8,000-$15,000 to initial startup costs.

Airbnb properties in Stock Island, Florida demonstrate strong profitability potential with average nightly rates ranging from $150-300 depending on property type and proximity to Key West, generating annual revenues of $35,000-75,000 for well-managed properties with 60-70% occupancy rates. Operating expenses typically consume 40-50% of gross revenue, including cleaning fees ($75-125 per turnover), property management (15-25%), maintenance and utilities ($3,000-6,000 annually), insurance ($2,500-4,000), and local taxes, resulting in net profit margins of 25-35% for successful operators. Success factors include strategic location within walking distance to marinas or with water views, professional photography showcasing the tropical setting, competitive pricing during peak season (December-April), and maintaining high guest ratings through responsive communication and quality amenities. Properties near the Stock Island Marina Village or with boat access command premium rates, with some waterfront units achieving $400+ nightly rates during Fantasy Fest and fishing tournaments, while investors focusing on the growing eco-tourism market and targeting fishing enthusiasts, boaters, and Key West overflow guests typically see ROI of 8-12% annually, though success heavily depends on effective marketing, consistent maintenance standards, and navigating Monroe County's strict short-term rental regulations implemented in recent years.

Airbnb investments in Stock Island, Florida typically generate annual ROI of 12-18% with cash-on-cash returns ranging from 8-14%, driven by the area's proximity to Key West and strong tourist demand. Properties in Stock Island, particularly those near marinas and fishing charters, can achieve occupancy rates of 65-75% annually with average daily rates of $150-220 depending on property size and amenities. Initial profitability usually occurs within 18-24 months, with full investment recovery typically achieved in 6-8 years. The market benefits from year-round tourism, fishing enthusiasts, and overflow demand from Key West's higher-priced accommodations, though investors should factor in hurricane insurance costs and seasonal fluctuations that can impact returns by 15-25% during slower summer months.

STRSearch leads the market in Airbnb investment property analysis for Stock Island, Florida, providing comprehensive data on rental performance and market trends. Local real estate agents specializing in short-term rental investments include Coldwell Banker Schmitt Real Estate with agents like Maria Rodriguez and Key West Realty's investment division, while Keller Williams Key West has dedicated STR specialists. National services include Mashvisor (founded 2014), which offers Stock Island market analytics, AirDNA providing rental data since 2015, and Awning's investment platform launched in 2017. RedAwning and Vacasa offer property management services for investors, while companies like Roofstock and Arrived Homes have expanded into the Florida Keys market. Local property management firms include Keys Holiday Rentals and Rent Key West, established in 2016 and 2018 respectively. BiggerPockets' marketplace connects investors with local wholesalers, and LoopNet features commercial properties suitable for STR conversion. Additional services include STR Helper for market analysis, Host Financial for STR-specific lending, and local contractors like Keys Construction Group specializing in STR renovations since 2019.