What if the busiest week on Duval Street could change how fast your home sells? In the Florida Keys, tourism doesn’t just fill hotels and bars. It shapes who tours your property, what investors will pay, and how you should time a listing. If you’re buying, selling, or underwriting a vacation rental, understanding these rhythms gives you an edge. Let’s dive in.
How tourism drives housing demand
Seasonal rhythms you can plan around
High season typically runs November through April. Winter visitors and snowbirds push up short-term rental demand and bring more out-of-state buyers to town. Spring and fall shoulder seasons can vary, often tied to events, fishing, and school calendars. June through November is both lower tourism and hurricane season, which can suppress bookings and slow buyer activity when storm projections hit the headlines.
Why visitation changes your buyer pool
When overnight stays rise, you see more investors underwriting short-term rentals, especially where STRs are legal. That can lift price-per-door for STR-capable condos and cottages. More visitors also means stronger in-person showing traffic from qualified buyers. In quieter residential pockets, there may be fewer comparable sales, so pricing requires careful storytelling and strategy.
Liquidity, comps, and STR tradeoffs
High-tourism micro-markets like Key West tend to produce more comps for STR-ready properties. But there is a tradeoff. Homes optimized for STR cash flow can sell at a premium, while resale to long-term residential buyers depends on local rules and neighborhood character. Make sure your pricing and marketing speak to both audiences when possible.
Key West: events, energy, and investor pull
What moves demand in Key West
Key West’s historic district, nightlife on Duval Street, Fantasy Fest, fisheries, and cruise calls fuel steady leisure travel. Cruise ships bring day visitors, which boosts restaurant and retail dollars and can spark same-day showing interest. They do not replace overnight visitors for STR revenue, so underwriting should focus on ADR and occupancy, not day-tripper traffic.
Housing implications on the island
Key West commands top-tier pricing for small condos and cottages that are walkable and STR-permitted. Investor interest is strong, competition is real, and presentation matters. If you’re listing, highlight legal STR status, booking history, and resilience upgrades to stand out. If you’re buying, expect to verify permitting and factor insurance and flood zones into your model.
Upper and Middle Keys dynamics
Islamorada: anglers and waterfront premiums
Islamorada draws higher-spending anglers and repeat visitors, with boutique lodging and luxury cottages. Deepwater dockage and boat access can command price premiums for both owner-occupiers and investors. If you own waterfront, your marketing should center on access and lifestyle, while your underwriting must include realistic dock, insurance, and maintenance costs.
Marathon: family-focused stays and space
Marathon offers more single-family inventory and attracts family vacationers and boaters, many from the drive market. STR demand exists, though ADRs may trail Key West. Buyers looking for a balance of returns and personal use often zero in here. If you’re selling, showcase floor plan flexibility, storage for gear, and local boating access.
Key Largo: gateway convenience and day trips
Key Largo benefits from proximity to Miami, diving at John Pennekamp Coral Reef State Park, and easy weekend trips. Day-trip traffic supports restaurants and can bring some showings, but it is typically less helpful for ADR-driven STR underwriting compared with Key West. If you’re investing, keep expectations grounded and verify monthly seasonality before you buy.
Access and timing: the practical effects
Airports and flights
Key West International Airport is the main air gateway to the Lower Keys. When flight availability improves, more buyers can visit for showings, and high season can feel even higher. Marathon has smaller regional service, while most Upper Keys visitors drive from Miami or Fort Lauderdale.
U.S. 1 and congestion
The Overseas Highway is your lifeline. Seasonal traffic affects how easy it is for buyers to tour multiple homes and how long they stay. If you’re scheduling showings, budget extra travel time and cluster appointments by submarket.
Cruise schedules vs. overnight demand
Cruise ship days lift foot traffic and retail sales in Key West. They are not a substitute for overnight stays when you are modeling STR revenue. Investors should keep cruise calendars in context and anchor projections to ADR and occupancy trends instead.
Rules, risk, and real costs you must respect
STR regulation varies by jurisdiction
Monroe County and each municipality manage STRs differently. Some areas limit new permits, require registration and inspections, or enforce occupancy and nuisance rules. Whether a property is legally eligible for STR use is a core value driver. Always confirm current status, permits, and any pending caps or moratoria.
Taxes and fees on short stays
Short-term rentals are subject to Florida state sales tax plus local discretionary sales tax and county tourist development tax. Underwriting should use net revenue after all taxes, platform fees, and cleaning expenses. Sellers should keep clear records of remittances to build buyer confidence.
Insurance and flood zones
Windstorm, hurricane, and flood insurance premiums have trended higher for coastal properties. FEMA flood zones and elevation drive mandatory coverage and pricing. Buyers should secure quotes early. Sellers should be ready with elevation certificates and resilience details like shutters or roof tie-downs.
Codes, resilience, and operating costs
Compliance, storm-hardening features, and post-storm repair timelines all affect your bottom line. Utility and septic-to-sewer rules can add costs and constrain redevelopment. Factor downtime into STR models and set aside reserves for storm repairs.
Seller playbook: timing, pricing, and proof
When to list for maximum turnout
To capture peak buyer visitation, list in late fall through early winter, typically November to February. Avoid hurricane season if you can. If you are targeting out-of-state investors, consider timing around, not on, major event weekends so qualified buyers can actually tour without crunch.
Pricing strategies that cover both buyers
If your home is STR-capable and legal, price with two lenses.
- Price to income for investors. Use capitalized NOI and local cap-rate norms informed by real performance.
- Provide residential comps for buyers who want to convert to longer-term or personal use, and explain the regulatory path.
If your home is not an STR, lean into winter buyer demand and highlight neighborhood amenities like dockage, parking, or hurricane upgrades. Good pricing is supported by clean documentation and a compelling lifestyle story.
Use dynamic demand proof in your listing
For STR properties, include 12 to 36 months of ADR and occupancy trends in your marketing packet to demonstrate seasonality and volatility. Show real booking calendars if available. Transparency builds trust and can shorten days on market.
Investor checklist: model it like a pro
Gather the right inputs
- ADR by month for your property type and zip
- Occupancy by month from host data or market sources
- Management, cleaning, utilities, repairs, property taxes, insurance, HOA, platform and marketing fees
- State and local taxes on short stays
- Debt service terms and lender requirements for STRs
- Capital reserves for storms and downtime
Build a month-by-month model
- Compute gross rental income by month, then roll up the year
- Subtract operating expenses and taxes to reach NOI
- Derive an implied price from your target cap rate, or test your debt service coverage
Stress-test before you commit
Run scenarios for ADR declines of 10 to 20 percent, occupancy drops of 15 to 30 percent, insurance spikes of 25 to 100 percent, and 60 to 120 days of storm-related downtime. If the deal still works, you are closer to a durable asset.
Due diligence for clean closings
- Verify STR permit or registration status and any pending restrictions
- Collect 12 to 36 months of booking history and P&L if marketed as an income property
- Order updated insurance quotes early
- Confirm FEMA flood zone and secure an elevation certificate if available
- Review code enforcement history and any noise or occupancy complaints
- For sellers, assemble compliance records and tax remittances to reduce buyer risk
Micro-market strategies that work
Key West: lean into lifestyle and legality
- Lead with legal STR status, booking history, and resilience upgrades
- Highlight proximity to historic district and walkability for demand and resale
- Time showings around event weeks to manage access while keeping energy high
Islamorada: sell the water and repeat stays
- Emphasize deepwater dockage, boat access, and storage
- Underwrite with realistic maintenance and insurance inputs
- Market to anglers and repeat visitors who value consistency and privacy
Marathon: balance returns and personal use
- Position larger single-family homes for flexible owner use and family rentals
- Focus on practicality: parking for trailers, gear storage, easy access to charters
- Price with an eye on ADR that trails Key West while underscoring value
Key Largo: convenience with measured expectations
- Promote quick access from Miami and weekend usability
- Underwrite carefully if your plan hinges on STR ADR; confirm seasonality
- Target buyers who want frequent personal use with supplemental income
What this means for you
Tourism in the Florida Keys isn’t a backdrop. It is a market engine that moves showings, pricing, and investor math across Key West, Islamorada, Marathon, and Key Largo. If you align your listing timing with high season, price to both STR and residential buyers where appropriate, and model month by month with real costs, you can unlock stronger outcomes.
Ready to put a plan together for your home or investment property? Schedule a complimentary market consultation with Unknown Company.
FAQs
How tourism affects housing demand in the Florida Keys
- Tourism increases investor interest in STR-capable homes, boosts in-person showings during high season, and shapes pricing where overnight demand is strong.
Listing timing for Key West sellers during high season
- Listing in late fall through early winter helps capture peak buyer visitation and can reduce days on market compared with hurricane season.
Cruise ship visitors and STR revenue in Key West
- Cruise ship traffic raises daytime retail activity but does not replace overnight stays, so it should not drive STR revenue assumptions.
STR regulation differences across Monroe County
- Rules vary by municipality, and permits or registrations can be limited or capped, so always verify legal STR status before underwriting or offering.
Insurance and flood zone impacts on Keys properties
- Windstorm and flood premiums can materially affect expenses; FEMA flood zones and elevation influence required coverage and rates, which impact cash flow and pricing.
Underwriting seasonality for Keys vacation rentals
- Use month-by-month ADR and occupancy, then stress-test for ADR declines, occupancy drops, insurance spikes, and storm-related downtime before you buy or list.
