Short‑Term Rental Investing in Kissimmee

Thinking about buying a vacation rental near Disney and wondering if Kissimmee is the right move? You’re not alone. With steady visitor demand and resort communities built for families, Kissimmee can be a strong market when you buy the right home and follow the rules. In this guide, you’ll learn where short‑term rentals commonly operate, what costs and taxes to expect, how seasonality affects bookings, and how to model realistic revenue before you commit. Let’s dive in.

Why Kissimmee works for STRs

Kissimmee sits just south of Orlando’s theme parks. Quick drives to Walt Disney World, Universal Orlando, and SeaWorld fuel year‑round demand from families and groups. Access to Orlando International Airport and regional convention centers adds another layer of bookings.

You’ll also see demand from sports tournaments, seasonal travel during school breaks and holidays, and convention traffic. Multi‑bedroom homes close to the attractions corridor tend to stay busy when priced and marketed well.

Where STRs commonly operate

Resort‑style communities

Many investors target gated, resort‑style communities with amenities like pools, clubhouses, and playgrounds. Common examples around Kissimmee include Windsor at Westside, Windsor Hills, Emerald Island, Storey Lake, Solara Resort, Reunion Resort, Formosa Gardens, and the ChampionsGate area. Always verify the municipal jurisdiction for any address, since some of these lie in unincorporated Osceola County or neighboring cities.

These communities often cater to vacationers, but rules vary. Some allow flexible short‑term renting, while others set minimum stays or require on‑site management. Read the HOA and rental program agreements before you make an offer.

Single‑family subdivisions

Traditional neighborhoods near I‑4 and US‑192 can also permit short‑term rentals, depending on zoning and HOA rules. Because policies differ block by block, you should confirm allowed uses in writing with the city or county and review the HOA’s covenants and restrictions.

Condos and townhomes

Condos and townhomes appear in older or mixed‑use areas. These can be attractive entry points, but they often come with more defined rental rules. Check minimum stays, guest registration processes, and whether the building has any rental caps.

Know the rules before you buy

HOA and resort rules to confirm

Before you fall in love with a property, confirm the community’s stance on short‑term renting. Key items to check in the governing documents include:

• Minimum rental term and any annual rental caps
• Required registration or permits, and any extra community fees per booking
• Whether you must use an on‑site rental desk or a specific manager
• Parking limits, occupancy rules, signage/advertising restrictions, and fines
• Noise, quiet‑hours, and guest behavior policies

City vs. county requirements

Rules differ between the City of Kissimmee, Celebration, and unincorporated Osceola County. Some jurisdictions require STR registration, a business tax receipt, proof of insurance, and compliance with building and safety standards like smoke and carbon monoxide detectors and proper egress.

Action step: Ask the City of Kissimmee or Osceola County planning or code enforcement to confirm the property’s address and STR status in writing. Save those records in your file.

What it really costs to operate

Recurring operating costs

Build a monthly and annual model that includes:

• Mortgage payments if financed
• Property taxes using the Osceola County Property Appraiser’s assessments
• Insurance suited for vacation rentals, including wind/hurricane and flood where applicable
• HOA or master association dues and any capital assessments
• Utilities: water, sewer, electricity, trash, cable/streaming, and high‑speed internet
• Management fees based on your chosen model
• Cleaning and turnovers, plus supplies and linens
• Maintenance and replacement reserves (furniture, appliances, small repairs)
• Platform and payment processing fees
• Marketing or channel manager tools if you go multi‑platform

HOA dues in resort communities can range from the low‑hundreds per month to several hundred dollars, depending on amenities. Get exact numbers from current HOA documents.

Taxes and permits

Florida imposes a 6% state sales tax on transient rentals. Osceola County and local municipalities may add a tourist development or transient rental tax. Hosts are responsible for collecting and remitting applicable taxes unless a platform does it for you. Verify the current Osceola County and City of Kissimmee procedures and any local licensing or business tax receipt requirements.

Budgeting tips

• Model conservative and optimistic scenarios. In your conservative case, assume lower occupancy and ADR, plus higher insurance and HOA costs.
• Include a capital expenditure reserve for furniture and appliance replacements.
• Get hard quotes: HOA dues, insurance premiums for STR use, and written management proposals.

Seasonality and demand patterns

Peak seasons typically align with school breaks: summer, spring break, Thanksgiving, and Christmas/New Year weeks. Conventions and theme‑park events can create spikes, especially near the attractions corridor.

Late summer into early fall, particularly August and September, often softens due to heat and hurricane season. Weekend bookings tend to be stronger for family properties, though homes near the parks can see steady mid‑week demand in high season.

Build realistic revenue projections

Use recent market data from multiple STR analytics platforms for the Kissimmee submarket. Then follow a simple framework:

1. Define your comp set. Choose 8–12 similar listings within 10–20 minutes that match bed count, amenities, and listing quality.
2. Gather ADR and occupancy by month. Monthly trends are more useful than a single annual average.
3. Estimate gross annual revenue. Sum monthly ADR times days in month times projected occupancy.
4. Subtract operating costs to calculate net operating income (NOI).
5. Run three scenarios. Conservative, baseline, and optimistic using different ADR/occupancy and cost assumptions.
6. Track key yields. Gross rental yield equals gross revenue divided by purchase price. Net cash yield equals NOI after debt service (or NOI if cash) divided by purchase price.
7. Do sensitivity checks. See how changes in occupancy, ADR, and management fees affect profitability.

Pro tip: Many online calculators are optimistic and may ignore HOA rental limits or mandatory on‑site programs. Trust verified platform data, not anecdotes.

Management models and fees

Decide how hands‑on you want to be, then price accordingly.

• Self‑management: You handle listings, guest communication, cleaning coordination, and maintenance. No recurring fee, but higher time cost and operational risk.
• Co‑hosting: You keep control of the listing and delegate guest messaging and turnovers. Fees commonly run 10–20% of revenue.
• Full‑service management: End‑to‑end pricing, guest support, cleaning, and maintenance coordination. Fees commonly run 20–35% of revenue, with cleaning typically charged to guests separately.
• On‑site/resort management: Some gated communities require the on‑site rental desk. Terms vary and may include per‑booking fees or revenue sharing.

If you prefer a more passive approach, model your returns with full‑service fees to stay conservative.

Due diligence checklist

Use this list to protect your investment before you go under contract:

• Obtain and read HOA/condo governing documents and recent meeting minutes. Look for any pending changes to rental rules.
• Ask the seller for verified rental income and expense history and booking records.
• Confirm permits or registrations if the property has operated as an STR.
• Get insurance quotes tailored to STR use, including wind/hurricane and flood coverage.
• Check flood zone status with FEMA maps and estimate flood insurance if needed.
• Confirm zoning and allowed uses with the City of Kissimmee or Osceola County in writing for the exact address.
• Estimate replacement reserves and get quotes for furnishing and amenity upgrades.
• Interview 2–3 local property managers and get written proposals.
• Build conservative and baseline financial models and stress‑test ADR, occupancy, and fees.

Common pitfalls to avoid

• Relying on annual averages instead of monthly ADR and occupancy trends
• Ignoring HOA rules that limit rental frequency, require specific management, or add per‑booking fees
• Underestimating insurance, HOA dues, or seasonal slowdowns
• Assuming you can opt out of an on‑site rental program when the community requires it

How The Home Squad can help

You deserve a clear, data‑minded plan for your Kissimmee investment. As a full‑service team with deep local knowledge across the I‑4 corridor, The Home Squad helps you identify STR‑friendly communities, request and review key HOA documents with you, and structure offers that reflect real operating costs and seasonality. Our goal is to guide you toward properties that align with your income targets and comfort level with management.

Ready to explore Kissimmee short‑term rentals with a team that understands both the neighborhood nuances and the numbers? Connect with The Home Squad to get started.

FAQs

What Kissimmee areas commonly allow STRs?

• Resort‑style communities frequently used by investors include Windsor at Westside, Windsor Hills, Emerald Island, Storey Lake, Solara Resort, Reunion Resort, Formosa Gardens, and the ChampionsGate area, but you should verify HOA rules and municipal jurisdiction for each address.

What taxes apply to Kissimmee vacation rentals?

• Florida charges a 6% state sales tax on transient rentals, and Osceola County or local municipalities may add tourist development taxes; verify current rates and who collects and remits for your bookings.

How does seasonality affect bookings in Kissimmee?

• Demand peaks during summer, spring break, Thanksgiving, and the winter holidays, while late summer and early fall often soften; events and conventions can create short spikes.

What are typical management fees for STRs?

• Co‑hosting commonly runs 10–20% of revenue, while full‑service management often ranges from 20–35%, with cleaning typically charged to guests separately.

What should I check before buying an STR?

• Get HOA documents and minutes, confirm city or county STR rules in writing, secure STR‑specific insurance quotes, validate flood zone status, review rental history, and model conservative and baseline scenarios.

Does Kissimmee require an STR permit?

• Requirements vary by jurisdiction; the City of Kissimmee, Celebration, and unincorporated Osceola County can have different registration, licensing, and safety standards, so confirm for the property address in writing.