Siesta Key Short‑Term Rental Income: How To Analyze Deals

Two weeks in February can make or break a Siesta Key rental year. If you want consistent cash flow, you need a local playbook that captures seasonality, fees, and HOA rules before you ever write an offer. In this guide, you’ll learn how to underwrite Siesta Key short-term rentals with a step-by-step model you can reuse on every deal. You’ll size demand by micro-area, set seasonal ADR and occupancy, map all expenses, and stress test returns so your numbers hold up. Let’s dive in.

Start with your product and guest

Define what you’re offering and who you’re serving. Your property type and guest profile shape pricing, occupancy, and costs.

• Property type: condo vs single-family, bedroom count, parking, and outdoor space.
• Micro-location: direct Gulf-front, partial view, walk minutes to Siesta Beach, bayfront dock, or near Siesta Village.
• Guest use case: couples weekends, family beach weeks, weddings, fishing and boating, or snowbird extended stays.
• Minimum stays and rules: set realistic minimum nights by season and confirm what your HOA or municipality allows.

Being precise here makes your comps and revenue assumptions much more accurate.

Map demand and seasonality on Siesta Key

Siesta Key’s calendar is not flat. Winter and early spring are peak months. Fall and early summer are shoulder periods. Summer tends to run lower occupancy, and hurricane season adds risk. Model these patterns month by month instead of using a single annual average.

Use these micro-areas when pulling comps and building your calendar:

• Siesta Beach central: highest demand for walkable or beachfront properties near the public beach.
• Crescent Beach and south Siesta: premium for a more private feel and select properties with higher per-night pricing.
• Siesta Village and Stickney Point: strong demand for walkable dining and nightlife; popular for shorter stays.
• Turtle Beach and back-bay: generally lower ADR than direct Gulf-front but attractive for boating or fishing guests.

Pull data from multiple sources like STR data providers, active Airbnb and VRBO comps, and local property managers’ booking curves. Never rely on one feed alone.

Price your nights by season

Set average daily rates by month or by banded seasons. Anchor your model with 3 to 6 high-quality comps per product type and weight them by bedroom count, proximity to the beach, view, parking, pool, and elevator access.

• Account for dynamic pricing. Many hosts use tools that lift ADR during peak windows.
• Check minimum-night rules on comps. A 7-night minimum often changes the booking pattern compared with 3-night policies.
• Track event spikes. Weddings and local events can boost weekend ADR in shoulder months.

Aim to build a rate table that mirrors how you intend to operate, not just what you see online today.

Set occupancy targets the right way

Occupancy is highly seasonal. Build it monthly or at least as peak, shoulder, and off-season bands. Confirm with local data sources and property manager calendars.

• Peak: expect materially higher ADR and occupancy in winter and early spring.
• Shoulder: fall and early summer can perform well with the right pricing.
• Summer: plan conservatively due to heat and storm risk.

Model your minimum stays. A 7-night minimum in peak season reduces turnovers and can improve average booking value but may increase vacancy gaps. Include blocked days for cleanings if your manager requires buffers.

Turn rates and occupancy into revenue

Once you have ADR and occupancy by season, compute top-line revenue with simple formulas.

• Gross potential rent per season: Average nightly rate × available nights.
• Effective rental revenue per season: Gross potential rent × occupancy rate.
• Total effective rental revenue: sum across all seasons.

If you plan to charge cleaning fees, model them separately as cleaning fee income. Do not net them against cleaning cost by default.

Model cleaning and turnovers

Cleaning is not just a pass-through. It affects cash flow and operations.

• Estimate average length of stay by season to derive bookings per year.
• Cleaning cost per turnover: get quotes by unit size and scope.
• Cleaning fee income: include it as a separate revenue line if you charge guests.
• Turnover buffers: add a time buffer between bookings if required, which reduces available nights.

Fewer, longer stays reduce cleaning cost and wear but may limit rate optimization. Build scenarios to see the impact.

Capture all fees and expenses

Underwrite with a full expense stack that reflects Siesta Key realities.

• Platform fees: model a conservative blended rate. Airbnb host fees are commonly around 3 percent for many hosts, but verify your account type.
• Property management: full-service vacation management often runs 20 to 30 percent of rental revenue. Confirm whether this is charged on gross or net of platform fees and taxes.
• HOA or condo fees: often one of the largest line items for condos. Review for included utilities, cable or internet, and any special assessments.
• Utilities: electricity for AC, water and sewer, trash, and high-speed Wi-Fi. Single-family homes usually run higher than condos.
• Insurance: homeowners plus wind or hurricane endorsements and flood insurance if in a FEMA flood zone. Coastal pricing can be significant.
• Taxes and licensing: state sales tax, tourist or bed taxes, and any county registration or business tax receipt. Determine which platforms collect and remit on your behalf and which you must file directly.
• Property taxes: pull current bills from county records for accuracy.
• Repairs, maintenance, and supplies: routine upkeep and guest consumables.
• Reserves for capital expenditures: allocate 5 to 10 percent of gross revenue or set a per-unit annual amount for furniture, appliances, and systems.

Management fee calculation nuance

Some managers charge a percentage on net revenue after platform fees. Others charge on gross. Confirm the basis in writing and mirror it in your model. Small differences here can materially change your NOI.

Debt and return metrics

If you use financing, include debt service to get to cash flow and returns.

• Net operating income: Effective rental revenue minus operating expenses.
• Cash flow before tax: NOI minus annual debt service.
• Cash-on-cash return: Cash flow before tax divided by total cash invested.

Your cash invested should include down payment, closing costs, initial furnishings, and working capital reserves.

Run sensitivity scenarios

Great underwriting shows how the deal performs when things go slightly better or worse than plan.

• Conservative: lower ADR and occupancy, higher insurance and HOA, and a higher management fee.
• Base: comps-aligned ADR, seasonally realistic occupancy, and average expense lines.
• Optimistic: higher ADR lift during peak months, efficient turnovers, and lower vacancy gaps.

Test thresholds like break-even occupancy, ADR cuts during summer, or a temporary closure due to a storm. Make sure the deal still meets your hurdle rate under conservative assumptions.

Confirm rules and compliance

Regulations and HOA rules can make or break returns.

• County and state requirements: verify transient rental tax registration, sales tax, and any county-level registration or inspection requirements.
• Platform tax collection: confirm which taxes are collected by the platform and which you must remit.
• Condo or HOA rules: minimum rental lengths, maximum number of rentals per year, owner occupancy requirements, guest screening rules, and quiet hours.

Always obtain current condo documents and check for pending rule changes. Treat compliance items as real costs in your model.

Condo vs single-family on Siesta Key

Both paths can work. The details decide your net yield.

• Condo pros: potentially lower price per bedroom, shared amenities that attract guests, exterior and common-area maintenance handled by the association, often easier remote operations.
• Condo cons: meaningful HOA fees, possible special assessments, rental restrictions or blackout periods, parking limits, and insurance gaps between unit and master policy.
• Single-family pros: higher ADR potential with private yard or pool and more control over rules and parking, strong appeal for groups and extended families.
• Single-family cons: higher maintenance and utility costs, larger CapEx needs, and possibly higher wind and flood insurance.

Underwriting takeaway: model HOA fees, insurance, and CapEx with care. A condo with a high HOA can compress returns despite a lower purchase price. A single-family may gross more but also demands larger reserves.

Decision drivers to weigh

• Net yield after all fees and reserves, not just ADR.
• Legal risk and the potential for rule changes, especially with condo boards.
• Financing differences for condos versus single-family properties.
• Exit strategy and buyer pool dynamics for each property type.

Build your underwriting worksheet

Create a repeatable structure so you can compare apples to apples across deals.

• Inputs: property type, micro-area, bedroom count, parking, pool, view, minimum stays by season.
• ADR table: monthly or seasonal ADR with notes on comps and dynamic pricing assumptions.
• Occupancy table: monthly or seasonal occupancy, including blocked turnover days.
• Revenue summary: gross potential rent, effective rental revenue, cleaning fee income.
• Expense stack: platform fees, management fees, HOA, utilities, insurance, taxes and licensing, property taxes, cleaning cost per turnover, maintenance and supplies, reserves.
• Debt: loan amount, rate, amortization, and annual debt service.
• Outputs: NOI, cash flow before tax, cash-on-cash return.
• Sensitivities: conservative, base, and optimistic cases for ADR, occupancy, and major expense lines.

Deal validation checklist

Use this quick list to pressure test any Siesta Key STR before you offer.

• Confirm exact micro-location and walking time to Siesta Beach access.
• Pull 12 to 24 months of occupancy and ADR comps from multiple STR data sources and local managers.
• Obtain cleaning quotes by unit size and at least two property management proposals.
• Request full HOA or condo documents and rental policy, including any pending changes.
• Get insurance quotes for homeowners, wind or hurricane, and flood if in a Special Flood Hazard Area.
• Confirm tax registrations and who collects and remits each tax on platform bookings.
• Review flood maps and elevation certificates where applicable.
• Run three scenarios and document break-even occupancy and ADR.
• Verify financing assumptions with a lender familiar with coastal condos and short-term rentals.

Local risk factors to budget

Siesta Key shares the same coastal risks that can impact income and expenses.

• Hurricanes and storms: potential closures, cancellations, and repair costs. Consider mitigation measures and cash reserves.
• Flood zones: insurance may be required by lenders and can be expensive. Elevation matters.
• Insurance market volatility: premiums can change quickly in coastal Florida, so keep assumptions conservative.
• Regulatory shifts: county rules or condo policies can tighten. Model a buffer for future changes.
• New supply and competition: track new inventory and renovated listings that may affect ADR.
• Neighborhood relations: good operations and quiet hours help reduce complaint-driven restrictions.

Ready to analyze a property together?

If you want a second set of eyes on ADR, occupancy, HOA rules, or management options, lean on local expertise. I help investors source the right properties, validate assumptions with local managers and cleaners, and model returns that stand up to real-world seasonality. Let’s build your Siesta Key underwriting with confidence. Connect with Marlin Yoder to get started.

FAQs

What occupancy and ADR should I model for a Siesta Key rental?

• Model seasonally by month, not a single annual figure, and expect materially higher ADR and occupancy in winter and early spring compared with summer.

How should I treat cleaning fees and costs in my pro forma?

• Record cleaning fee income as a separate revenue line and model cleaning cost per turnover based on quotes, since guest fees may not fully cover actual costs.

How much should I allocate for reserves and CapEx on Siesta Key?

• A conservative rule is 5 to 10 percent of gross revenue or a per-unit annual budget that reflects unit age, furniture, pool equipment, and coastal wear.

What are typical platform and management fees for vacation rentals?

• Platform host fees often run around 3 percent on some accounts, and full-service management commonly ranges from 20 to 30 percent of rental revenue.

How do condo rental rules affect revenue and value on Siesta Key?

• Minimum stays, rental caps, and blackout periods can constrain bookings and reduce liquidity, so always obtain and underwrite current HOA documents before offering.

How do I estimate coastal insurance costs for a Siesta Key STR?

• Request quotes from local brokers for homeowners, wind or hurricane endorsements, and flood if in a high-risk zone, and use conservative assumptions in your model.