Kissimmee: Long-Term Rental vs Short-Term Rental

The Default Assumption Is Wrong

Ask anyone about investing in Kissimmee and you'll hear the same thing: "Buy near Disney, put it on Airbnb, make a killing."

It sounds obvious. Kissimmee sits 15 minutes from Disney World and Universal. Millions of tourists need places to stay. Short-term rentals must be the play.

But when you actually run the numbers — real numbers with real taxes, real management costs, and real vacancy — the picture gets complicated. A long-term rental with stable tenants and lower operating costs may actually put more money in your pocket.

Let's compare them head-to-head.

The Properties: Apples to Apples

To make this comparison fair, we're using two realistic Kissimmee investment scenarios:

Different property types, different price points — but both represent the most common entry point for each strategy in Kissimmee.

STR Revenue: The Headline Number vs. Reality

What You'll Hear

"Kissimmee Airbnbs gross $41,000-$46,000 per year." That's what the data platforms say — AirDNA, Airbtics, and Mashvisor report average annual STR revenue in that range. Some sources report as low as $36,000. The range depends heavily on property size, location, and management quality.

What You Won't Hear

That gross number gets cut significantly before anything hits your bank account.

STR Revenue Breakdown (4BR Kissimmee Home)

Wait — negative cash flow?

Yes. At average performance levels, a Kissimmee STR on a financed property runs significantly negative. The 2025 Airbnb fee restructure (from 3% host fee to 15.5% host-only fee) made this worse — platform costs alone increased by over $5,000/year. The math only works if you:

1. Outperform averages significantly (top 25% of listings)
2. Self-manage (saving the 22% management fee)
3. Buy with more cash down (reducing mortgage burden)
4. Land in a high-demand micro-location (Reunion Resort, ChampionsGate)

The Top-Performer STR Scenario

Let's be generous and model a well-optimized STR:

Even top performers struggle to cash-flow positive with financing and professional management. With the 2025 Airbnb fee restructure (15.5% host-only fee), margins are even thinner than they were 12 months ago. The STR play in Kissimmee only reliably works as a cash purchase or with heavy self-management.

LTR Revenue: Less Exciting, More Predictable

The 4-Unit Long-Term Rental Model

That's $9,574 positive cash flow from day one, with professional management, at current market rents.

Head-to-Head: The Full Comparison

The Hidden Costs Nobody Talks About

STR: Death by a Thousand Cuts

1. The 13.5% Tourism Tax (and Who Collects What) Kissimmee STRs owe 6% Florida sales tax + 6% Tourist Development Tax + 1.5% Discretionary Surtax on every booking. Airbnb now collects the 6% state sales tax automatically, but Osceola County is not contracted with Airbnb, VRBO, or any other platform for the Tourist Development Tax or surtax. You or your manager must file and remit that 7.5% monthly with the county tax collector.

Many owners don't discover this until they receive a compliance notice. Back taxes plus penalties add up fast.

2. HOA Surprises Most STR-zoned communities in Kissimmee are resort-style with HOAs. Fees range from $150-$350/month ($1,800-$4,200/year), with premium communities on the higher end. Some HOAs have additional restrictions: minimum stay requirements, guest registration fees, occupancy caps, or seasonal blackout dates that override county zoning.

Always verify HOA CC&Rs before purchase — county STR zoning permission doesn't override HOA restrictions.

3. Cleaning and Turnover At $100 per turnover and an average of 49 turnovers per year, cleaning alone costs $4,900. Add linen replacement, damaged items, and deep cleaning every quarter, and turnover costs approach $6,000-$7,000 annually.

4. Market Saturation Kissimmee has approximately 2,000-2,300 active Airbnb listings and over 14,000 vacation rentals in the broader area. On BiggerPockets forums, investors describe a "race to the bottom" dynamic where large homes compete primarily on price. New listings face an established market with reviews and repeat guests.

LTR: Simpler but Not Free

1. Higher Entry Price A 4-unit multifamily in Kissimmee runs $550-$625K vs. $400-$500K for an STR home. Down payment is $25K higher.

2. Tenant Risk Florida landlord-tenant law favors tenants in some respects. Eviction timelines can run 30-60 days. Screen thoroughly — hospitality workers with variable hours need careful income verification.

3. Rent Growth Uncertainty Kissimmee rents are currently flat (-0.1% YoY). While Epic Universe and population growth support moderate increases, LTR rents won't spike like a well-timed STR during spring break.

When STR Actually Wins

STR isn't always the wrong choice. It works in specific scenarios:

Cash purchase: Remove the mortgage and the STR math changes completely. $43,500 gross - $23,000 expenses = $20,500 net. On a $450K cash purchase, that's a 4.6% return with appreciation upside.

Self-managed, local owner: Cut the 22% management fee and you save $9,570/year. If you live nearby and enjoy hospitality operations, self-management can push a top-performing STR into positive cash flow territory — though barely.

Premium property in top community: Reunion Resort and ChampionsGate properties with pools, game rooms, and themed bedrooms can gross $55-70K+. At those revenue levels, even with full management, the numbers work.

Hybrid strategy: Rent long-term in low season (September-January), short-term in peak season (March-July). Requires more complex management but captures the best of both.

When LTR Wins

Out-of-state investor: You live in New York (or anywhere other than Kissimmee). STR management from 1,000 miles away is a full business operation. LTR management is a monthly check-in with your property manager.

Passive income goal: LTR produces predictable monthly cash flow with minimal involvement. STR requires constant optimization — pricing adjustments, guest communication, review management, seasonal marketing.

Portfolio building: LTR cash flow ($9,574/year) reliably funds your next acquisition. STR revenue volatility makes it harder to project when you can deploy capital for the next deal.

First Kissimmee investment: If this is your first property in the market, LTR lets you learn the area, build a team, and understand tenant dynamics before taking on the complexity of STR operations.

The 5-Year Wealth Comparison

Let's project both strategies over 5 years with realistic assumptions:

Even in the most favorable STR scenario (top performer + self-managed), the LTR 4-unit creates more wealth over 5 years with significantly less effort.

Decision Framework

Choose STR if:

• You're buying with cash (no mortgage)
• You live in Kissimmee or can self-manage
• You have hospitality/operations experience
• You're targeting a premium resort community
• You enjoy running a micro-business (not passive investing)

Choose LTR if:

• You're financing the purchase
• You're investing from out of state
• You want predictable, passive cash flow
• This is your first Kissimmee property
• You're building a portfolio (need reliable capital recycling)

The contrarian take: Most Kissimmee investing content pushes STR because that's the exciting story. But the boring story — a 4-unit with 12-month leases, 8% management, and $9,500+ annual cash flow — is what actually builds long-term wealth for most investors.

Bottom Line

Kissimmee STRs are a business. Kissimmee LTRs are an investment. Both can work, but they require different capital, different skills, and different expectations.

If you're an experienced operator who lives nearby and can run a hospitality micro-business — STR has a higher ceiling.

If you're a Capital Region investor adding Kissimmee for cash flow diversification — LTR has a higher floor and a more predictable path to wealth.

The right answer depends on who you are, not where the property is.

Related Questions Investors Ask

• What are the short-term rental regulations in Kissimmee?
• How much does an Airbnb property manager charge in Kissimmee?
• What's the average occupancy rate for Kissimmee vacation rentals?
• Can I convert an STR to a long-term rental in Kissimmee?
• What insurance do I need for a Kissimmee rental property?