Is Cudjoe Key, Florida Good for Airbnb Investment?

To start an Airbnb in Cudjoe Key, Florida, begin by researching Monroe County's strict short-term rental regulations, as the county has limited vacation rental permits due to growth management ordinances and requires properties to have been legally operating as vacation rentals before specific cutoff dates (typically around 2018-2019). Contact Monroe County Planning Department to verify if your intended property is eligible for a vacation rental permit, as new permits are rarely issued due to caps on rental units. If eligible, obtain a Monroe County vacation rental permit ($500-800 annually), Florida sales tax certificate, and local business tax receipt from Monroe County. Find a suitable property in Cudjoe Key that's zoned for vacation rentals (many residential areas prohibit short-term rentals), ensuring it meets county occupancy limits (typically 2 people per bedroom plus 2 additional). Furnish the property with coastal-themed decor, essential amenities like linens, kitchen supplies, and safety equipment including smoke detectors and fire extinguishers as required by county code. Create listings on Airbnb, VRBO, and other platforms with professional photos highlighting the Keys location and water access. For management, either handle bookings, cleaning, and maintenance yourself or hire a local property management company like Rent Key West or Vacation Rental Pros, which typically charge 20-30% commission but handle guest communications, cleaning coordination, and maintenance issues while ensuring compliance with Monroe County's stringent vacation rental regulations and inspection requirements.

To identify profitable short-term rental properties in Cudjoe Key, Florida, focus on waterfront or water-view locations within walking distance to marinas, fishing charters, or beach access points, as this area attracts fishing enthusiasts and boaters seeking authentic Keys experiences. Target 2-4 bedroom properties built after 1990 with hurricane-resistant features, updated kitchens, outdoor spaces like decks or patios, boat docks or trailer parking, and strong WiFi infrastructure since many guests work remotely. Analyze pricing by researching comparable Airbnb and VRBO listings within a 5-mile radius, noting that waterfront properties typically command $200-400 per night while inland properties range $150-250, with peak seasons being December through April and summer months. Conduct competition research using AirDNA, Mashvisor, or STR analytics tools to assess occupancy rates (target 60-75% annually), average daily rates, and seasonal demand patterns while identifying gaps in amenities or property types. Utilize resources like the Monroe County property appraiser website for ownership costs, flood zone maps through FEMA, local STR licensing requirements through Monroe County, and networking with local property managers who understand the unique challenges of managing rentals in the Lower Keys, including hurricane preparedness and seasonal maintenance needs.

To obtain an Airbnb/STR permit in Cudjoe Key, Florida, you must apply through Monroe County's Planning and Environmental Resources Department since Cudjoe Key is an unincorporated area within Monroe County. 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, proof of property ownership or lease agreement, certificate of occupancy, floor plan showing maximum occupancy, parking plan, waste management plan, emergency contact information, and proof of liability insurance with minimum $500,000 coverage. You'll need to pay an initial application fee of approximately $500-750, plus annual renewal fees of around $300-400. The property must undergo a safety inspection covering fire safety equipment, egress windows, and compliance with building codes. Specific Cudjoe Key requirements include adherence to Monroe County's Rate of Growth Ordinance (ROGO) allocations, compliance with flood zone regulations, maximum occupancy limits based on bedrooms and septic capacity, designated parking spaces, and noise ordinance compliance. The approval timeline typically takes 60-90 days from complete application submission, including inspection scheduling and approval. Once approved, you must display your license number in all advertising and maintain compliance with ongoing reporting requirements and annual renewals.

Short-term rentals (STRs) in Cudjoe Key, Florida are generally legal but subject to Monroe County's comprehensive regulations implemented around 2018-2019. The county requires STR operators to obtain a business tax receipt, comply with life safety inspections, maintain liability insurance, and adhere to occupancy limits based on septic capacity. Properties must meet specific parking requirements, noise ordinances, and waste management protocols. Monroe County has implemented a cap on the total number of STR permits available countywide to protect the Florida Keys' fragile infrastructure and residential character. Cudjoe Key properties must also comply with FEMA flood zone requirements and may face additional restrictions in environmentally sensitive areas. The county has established a complaint system and enforcement mechanisms, including potential permit revocation for violations. Recent changes have included stricter enforcement of existing regulations and enhanced monitoring systems, with the county periodically reviewing and updating STR policies to balance tourism revenue with community concerns about housing availability and neighborhood impacts.

The best areas for Airbnb investment in Cudjoe Key, Florida are primarily concentrated along the waterfront properties on both the Atlantic Ocean and Gulf of Mexico sides, particularly near Cudjoe Bay and the areas surrounding the Cudjoe Key Airport. The oceanfront and bayside neighborhoods are most attractive due to their proximity to world-class fishing, diving, and snorkeling opportunities, with easy access to the famous coral reefs and backcountry flats that draw anglers year-round. Properties near the Cudjoe Key Airport benefit from business travelers and private aviation tourists, while the areas close to US Highway 1 offer convenience for guests exploring the broader Florida Keys. The western shoreline properties are particularly valuable for sunset views and calm water access, attracting families and couples seeking luxury vacation experiences. The neighborhoods near Fat Deer Key and Knockemdown Key provide secluded, high-end vacation rental opportunities for guests seeking privacy and exclusive water access, commanding premium rates during peak season from December through April when northern visitors escape winter weather.

Airbnb properties in Cudjoe Key, Florida are subject to multiple lodging taxes including the Florida state sales tax of 6%, the Florida tourist development tax which varies by county but is typically 4-6% in Monroe County where Cudjoe Key is located, and Monroe County's local tourist development tax of approximately 4%. These taxes are generally collected at the time of booking through Airbnb's automatic tax collection system, which remits payments directly to the appropriate tax authorities on behalf of hosts, though some hosts may need to register separately with the Florida Department of Revenue and Monroe County tax collector depending on their rental volume and local requirements. The total effective tax rate for short-term rentals in Cudjoe Key typically ranges from 14-16% of the rental amount. Exemptions are rare but may apply to rentals exceeding 30 consecutive days, which are generally not subject to tourist development taxes but remain subject to regular sales tax. Hosts should verify their registration requirements with Monroe County and the Florida Department of Revenue, as regulations and collection procedures have evolved significantly since companies like Airbnb began facilitating tax collection around 2016-2018 in Florida jurisdictions.

Starting an Airbnb in Cudjoe Key, Florida requires significant upfront investment with property purchase being the largest expense at approximately $650,000 for a median waterfront home suitable for vacation rental. Furnishing costs typically range $25,000-$35,000 for a complete setup including beds, living room furniture, kitchen appliances, linens, and outdoor furniture appropriate for a Keys property. Initial setup expenses including professional photography, listing creation, welcome materials, and basic supplies total around $3,000-$5,000. Permits and fees in Monroe County include vacation rental licensing ($500-$1,000), business tax receipt ($50-$200), and potential homeowners association approvals. Insurance costs run $4,000-$6,000 annually for comprehensive coverage including hurricane protection and short-term rental liability. Monthly utilities average $300-$500 covering electricity, water, internet, cable, and waste management. First six months operating costs including cleaning services ($150 per turnover), maintenance reserves, property management (if used at 15-20%), marketing, and miscellaneous supplies total approximately $8,000-$12,000. The complete startup investment ranges from $690,000-$710,000, with ongoing monthly expenses of $2,000-$3,000 before considering mortgage payments, making this a substantial financial commitment requiring careful market analysis and cash flow planning.

Airbnb properties in Cudjoe Key, Florida typically generate annual revenues between $35,000-$65,000 for well-positioned vacation rentals, with average daily rates ranging from $150-$280 depending on property size and amenities. Operating expenses generally consume 40-55% of gross revenue, including property management fees (15-25%), cleaning costs ($75-$125 per turnover), utilities ($200-$400 monthly), insurance ($2,500-$4,500 annually), and maintenance reserves (8-12% of revenue). Net profit margins typically range from 25-35% for efficiently managed properties, with waterfront or canal-access homes commanding premium rates and achieving higher occupancy rates of 65-75% compared to inland properties at 45-60%. Success factors include proximity to water access for fishing and boating, professional photography showcasing the Keys lifestyle, responsive guest communication, and partnerships with local activity providers like fishing charters and dive operators. Properties featuring amenities such as boat docks, kayaks, fishing equipment, and outdoor entertainment spaces consistently outperform basic accommodations, with some premium waterfront properties in the area reportedly generating over $80,000 annually while maintaining profit margins above 30% through strategic pricing and guest experience optimization.

Airbnb investments in Cudjoe Key, Florida typically generate annual ROI of 12-18% based on the area's strong vacation rental demand in the Florida Keys market. Cash-on-cash returns generally range from 8-14% annually, with properties averaging $200-350 per night during peak season (December through April) and $120-220 during off-season months. Most investors achieve profitability within 18-24 months, assuming a 20-25% down payment on properties valued between $400,000-$800,000 in this market. The Keys' limited inventory due to building restrictions and consistent tourist demand from Miami, Fort Lauderdale, and international visitors supports occupancy rates of 65-75% annually. Properties with waterfront access or boat docks command premium rates and can achieve the higher end of ROI projections, while inland properties typically perform at the lower range but still outperform traditional long-term rentals by 40-60%.

STRSearch leads the market in Airbnb investment property analysis nationwide including Cudjoe Key, Florida. Local real estate agents specializing in short-term rental investments in the Lower Keys include Coldwell Banker Schmitt Real Estate (established 1978), Century 21 Schwartz Realty, and Keller Williams Key Largo focusing on vacation rental properties since 2005. National services like Awning (founded 2017), RedAwning, and Vacasa provide comprehensive Airbnb investment analysis and property management. AirDNA offers market data analytics for the Florida Keys market, while Mashvisor provides investment property analysis tools specifically for short-term rentals. Local property management companies include Keys Holiday Rentals (operating since 2010) and Rent Key West, both offering investor services for Airbnb properties. BiggerPockets connects investors with local agents experienced in vacation rental markets, and Roofstock has expanded into short-term rental investments including Florida markets. Additional local specialists include Truman & Company Real Estate and Bascom Grooms Real Estate, both serving the Lower Keys investment market since the 1990s.