Trying to choose between Siesta Key and Longboat Key for a rental investment? You are not alone. Both islands are beloved Gulf Coast destinations, but they perform differently depending on unit type, rules, and the guests you plan to attract. In this guide, you will get a clear, side‑by‑side view of guest demand, seasonality, revenue patterns, HOA and regulatory hurdles, insurance, and the practical steps you should take before you buy. Let’s dive in.
Quick take: how the islands differ
Siesta Key offers a wide mix of condos and some single‑family homes close to a world‑famous public beach. You tend to see strong short‑stay demand from families and vacationers who want easy beach days and quick getaways. That often translates to higher occupancy and more frequent turnovers.
Longboat Key skews more residential and upscale. Inventory includes luxury condos and single‑family homes with private beach access or marina proximity. Guests often stay longer, seek a quieter environment, and accept higher average daily rates for quality and amenities. Booking volume can be lower, but rates and stays may run higher.
The investment tradeoff is simple. Siesta Key leans toward volume and turnover. Longboat Key leans toward higher ADR and longer stays. Your outcome depends on the specific unit, HOA rules, your pricing strategy, and how you operate the property.
Who your guests are
Siesta Key guest profile
On Siesta Key, many guests are short‑stay leisure travelers. Think weekenders, weeklong family trips, and multigenerational groups who prioritize beach days and easy access to Sarasota attractions. You will see strong interest during school breaks, summer, and peak winter.
Event and wedding guests also favor Siesta Key because of public beach access and proximity to Sarasota venues. This can create compressed booking windows and a steady flow of 2 to 7‑night reservations.
Longboat Key guest profile
Longboat Key tends to attract couples and travelers who want a quieter, more refined stay. Boaters and fishing groups also book here due to nearby marinas and charters. Winter snowbirds return for multi‑week or even multi‑month stays, and repeat bookings are common.
The result is a booking mix that favors longer stays and potentially higher ADR. The guest count may be smaller, but the spend per booking is often higher compared to short‑stay condos.
Booking length and lead time
Siesta Key bookings often run 2 to 7 nights with shorter lead times. Many guests plan last minute weekend or short vacation trips. That means more turnovers and more cleaning cycles, but also a lot of pricing opportunities around peak weeks.
Longboat Key sees more 7 to 30‑plus night stays and longer lead times, especially for the December to April snowbird season. Repeat guests sometimes book months or even a year ahead, which can smooth your winter revenue plan.
Seasonality and pricing patterns
Both islands share a strong winter season from December through April. Demand is fueled by snowbirds and peak‑season tourism. You will also see shoulder strength in May and November.
Summer is mixed. Florida heat and storms slow long‑stay demand, but family travel picks up in Siesta Key. Late summer and early fall are usually the softest in occupancy and ADR, so plan your pricing accordingly.
Practical tips:
- Use minimum stays to balance turnover with rate. For example, shorter minimums during peak holidays may boost occupancy, while longer minimums in winter can yield longer bookings.
- Consider whether you want one solid monthly winter booking or multiple shorter, higher‑rate stays. Both can work if you plan your calendar and cleaning team well.
Revenue potential vs. operating costs
What drives revenue
- ADR: Inventory and clientele often push Longboat Key rates higher, especially in luxury condos and waterfront homes. Siesta Key can deliver strong ADR during peak weeks due to proximity to Siesta Beach and heavy demand.
- Occupancy: Seasonality is real. Well‑located units can approach very high occupancy in peak months and drop off in late summer or early fall.
- Booking mix: Platform bookings, direct bookings, and local property managers affect net revenue after commissions. Ancillary fees like cleaning or parking can offset costs if structured well.
Before you buy, use local short‑term rental analytics and talk to experienced property managers who can provide comps for your building or address. Always get unit‑specific estimates rather than relying on island averages.
Common expenses to budget
- Property management: Full service for short‑term rentals typically runs about 20 to 35 percent of gross rent, depending on services.
- HOA or condo fees: High‑amenity buildings may have higher monthly dues, which can reduce net cash flow. Know what utilities and services are included.
- Cleaning and turnover: More short stays mean more turnover costs and more wear on linens and supplies.
- Marketing and platform fees: Account for platform service fees and any direct booking costs.
- Repairs and reserves: Budget for storm preparation, impact windows or shutters, and periodic capital projects.
- Taxes: Plan for state sales tax and local tourist development taxes, plus income tax on net rental income.
Financing basics
Loan type matters. Investment property loans and second‑home loans have different down payment and rate structures. Condo financing can be complex if a building is heavy on short‑term rentals or not on approved lists for certain loan products. Underwriters often want rental history or conservative pro forma rents. Cash buyers may have an edge in coastal markets.
Work with a mortgage broker who knows Florida coastal condos and the nuances of short‑term rental buildings.
Taxes and depreciation basics
Rental income is taxable, and you can typically deduct mortgage interest, property taxes, insurance, management fees, utilities, repairs, and depreciation. Personal use can limit deductibility, so check the rules before you plan extended owner stays. You also need to collect and remit transient rental taxes on time. A local CPA can help you model these items before you commit to a purchase.
Rules that can change your returns
Local registration and compliance
Rules vary between the Town of Longboat Key and unincorporated Sarasota County, which includes much of Siesta Key. You may need business licenses, registrations, safety checks, and tax remittance. Noncompliance can mean fines and loss of rental privileges. Verify current requirements before you buy.
HOA and condo restrictions
Many associations set minimum stay lengths and rental caps. A 30‑day minimum, seasonal caps, or a limited number of rentable units can make short‑term use impractical. Some associations also require manager registration, guest screening, or specific rental contracts. Review CC&Rs, bylaws, rental policy addenda, and association financials in detail.
Insurance and physical risks
Coastal properties face wind and flood risk. Insurance costs and deductibles can be significant, and some buildings have coverage constraints or high master policy deductibles. Mitigation such as impact windows and hurricane shutters may lower risk and help with premiums. Always request quotes early and confirm the scope of the condo master policy.
Building and safety requirements
Some jurisdictions require smoke detectors, life safety measures, evacuation info, and clear occupancy standards. Parking limits can affect guest experience and compliance. Understand building rules and local codes before you market the unit.
Due diligence checklist
Use this list to validate both islands at the unit level.
Revenue and market validation
- Ask for historical rental income and occupancy for the specific unit or building.
- Run comps with short‑term rental data tools and look at active listings for ADR, minimum nights, and fees.
- Get pro forma scenarios from local managers for optimistic, moderate, and conservative cases.
Regulatory and HOA verification
- Obtain full HOA or condo documents and confirm minimum stay, rental caps, permitted platforms, parking, and pet rules.
- Ask about any pending rule changes, special assessments, or litigation.
- Verify local registration and tax remittance requirements with the county or town.
Financing, tax, and insurance checks
- Seek pre‑approval with lenders experienced in Florida coastal condos and ask about condo approvals.
- Consult a CPA for income tax, depreciation, and transient tax planning.
- Obtain windstorm, flood, and liability quotes before you close and review condo master policy details.
Property condition and resilience
- Check elevation and FEMA flood zone. Get an elevation certificate if available.
- Inspect impact windows, shutters, roof, HVAC age, plumbing, and any moisture history.
- Budget reserves for storm events and potential post‑storm vacancy.
Operational planning
- Decide whether to self‑manage or hire a local manager. Compare fees and service levels.
- Build a full expense model, including cleaning per turn, utilities, HOA dues, and marketing.
- Prepare guest rules, arrival guides, parking maps, and emergency contacts.
Exit planning and resale
- Review resale comps and days on market for similar units.
- Consider buyer pool size. Siesta Key condos often see broader buyer interest, while Longboat luxury units may trade within a smaller upscale segment.
- Understand how condo financing rules might affect your future buyer.
Which island fits your plan
Choose Siesta Key if you want higher booking volume, many price points, and steady short‑stay demand near a major public beach. Expect more competition and higher turnover costs, but also frequent pricing opportunities during peak weeks and holidays.
Choose Longboat Key if you want higher ADR, longer stays, and a quieter setting that appeals to couples, boaters, and seasonal guests. Expect higher purchase prices and potentially stricter building rules, but also a guest base that books ahead and returns.
If winter income is your priority, both islands can perform well. Longboat Key may deliver longer seasonal bookings, while Siesta Key can mix snowbirds with shorter tourist stays for a diversified calendar.
How we can help
You do not have to navigate this alone. Flota’cal Real Estate & Property Management brings brokerage, long‑term property management, and vacation rental operations together under one roof. Our team aligns your purchase with a management plan, from HOA review and insurance quotes to marketing and guest service through a professional portal with owner access and 24/7 maintenance workflows.
Whether you plan to self‑use, rent short term, or hold long term, we help you compare Siesta Key and Longboat Key at the building level and set up an operating model that fits your goals. If you are ready to evaluate specific addresses, request unit‑level comps, rental history, and association documents so you can move forward with confidence.
Ready to talk through your plan and tour properties? Connect with The Pergerson Group to get started.
FAQs
What delivers higher rental income on average, Siesta Key or Longboat Key?
- It depends on the unit, HOA rules, and operations; Siesta Key often favors higher occupancy and turnover, while Longboat Key can command higher ADR and longer stays.
Are short‑term rentals allowed on both islands?
- Rules vary by jurisdiction and building; verify current requirements with Sarasota County for Siesta Key and the Town of Longboat Key, plus your HOA or condo association.
What minimum stay rules should I expect in condos?
- Many associations enforce minimums such as 30 days or limit the number of rentals per year; review the rental policy addenda for each building.
How does hurricane season affect returns?
- Late summer and early fall can be softer in demand and involve storm risk; insurance costs, deductibles, and preparedness planning should be part of your budget.
What financing issues affect condo short‑term rentals?
- Some lenders require condo project approvals and may limit financing if a building relies heavily on short‑term rentals; work with a broker familiar with Florida coastal condos.
What taxes apply to short‑term rentals in Sarasota County?
- You typically need to collect and remit state sales tax and local tourist development taxes, and report net rental income for income tax; confirm current rates and rules before you list.
