Greater Orlando · Investor Assessment
Know how you'll make money before you buy.
Short-term and long-term rentals are not two versions of the same deal. They are different businesses, in different jurisdictions, with different legal footing. Nine questions to find out which one you're actually built for — and where in Central Florida it's legal.
About seven minutes. No email to start. Lake, Osceola, Polk and west Orange counties — ChampionsGate and Four Corners through Clermont, Horizon West, Windermere and Winter Park.
Short-Term Rental
82% strategy fit · mid-term as the fallback
The premise
Most investors pick the property, then discover the rules.
The question that decides your return in Central Florida is not which house. It is which business — nightly hospitality or residential tenancy — and whether the parcel you're about to put under contract is legally allowed to run it.
Those two things are set at the jurisdiction level, and greater Orlando is a mosaic. Whole-home nightly rental is permitted by right in parts of unincorporated Osceola County. It is prohibited outright in Winter Park, at any duration under a month. Two miles away in Maitland it is a permitted use in every residential district — but only if the owner lives there, which closes the same door by a completely different mechanism. Horizon West is unincorporated Orange County, where nightly rental is prohibited unless that specific Planned Development expressly permits it.
You can buy the perfect vacation-rental house and find out at closing that the county never approved the subdivision for it.
The trap is the mailing address. A property advertised as "Kissimmee" or "Davenport" is, more often than not, in unincorporated county — a different code, a different overlay, a different approval path than the city whose name is on the envelope. Buyers make expensive mistakes on exactly this point.
So this assessment does two things. It works out whether your goals, your tolerance for volatility, and your appetite for operating a hospitality business point toward short-term, long-term, or mid-term. Then it ranks the ten Central Florida investor markets against that answer, and tells you plainly where each one stands legally — including the four where the honest answer is that you need a written determination before you sign anything.
| Marketed as | Actually governed by | 2025 millage |
|---|---|---|
| ChampionsGate | Unincorp. Osceola County | 13.8543 |
| Davenport resort homes | Unincorp. Polk County | 12.9761 |
| Horizon West | Unincorp. Orange County | 16.09–18.14 |
| Most of "Windermere" | Unincorp. Orange County | 16.09–18.14 |
City of Davenport itself is 19.3579 mills — a 49% higher tax burden than unincorporated Polk on an identical house a few hundred yards away. The Town of Windermere is roughly 1,700 acres and 2,900 people; most of the 34786 mailing area is not in it.
How it works
Strategy first, then jurisdiction, then the property.
Step one
Answer nine questions
About your capital, your horizon, how involved you want to be, and how much regulatory risk you'll actually accept. Not about your credit score. No email required to start.
Step two
Get your strategy and your markets
A primary strategy with a fit score, the runner-up if it's close, and the ten markets ranked against your answers — plus the ones you should rule out and why.
Step three
Unlock the full market guides
Legal standing, current price feel, the real operating cost stack, what a typical year looks like, and who should look elsewhere. Add your details and we'll send them.
The nine markets
Nine ways to own an investment property in Central Florida.
Lake, Osceola, Polk and west Orange, plus Winter Park and Maitland — the counties the Bella Trae Team actually works. The status chip is the short-term-rental position for a non-owner-occupied whole-home nightly rental, verified as of September 2026. Two are specialist markets that appear in your results only if you ask for that kind of tenant.
Status reflects our reading of published ordinances, county zoning tables and official county lists as of September 1, 2026. It is a starting point, never a substitute for a written zoning verification on the specific parcel. Rebecca Hamaoui is a licensed REALTOR, not a land-use attorney or a CPA.
Your goals
Question
Help text
Your assessment
PRIMARY STRATEGY
Strategy
Reasoning
Strategy fit
Your guides, and first look at what never reaches the MLS
- The full guide to every market you matched. Legal standing with the code citation, current price and rent data, the real operating cost stack, what a typical year looks like, and who should look elsewhere.
- Off-market and pre-market deals in those same markets. Pocket listings, builder inventory before it lists, and investor resales the Bella Trae Team sees before they reach the portals.
Your guides arrive in one email. Deal alerts only if you ticked the box. We never sell or share your details.
Unlocked. Your guides are open in the market list below.
Your markets, ranked
Where this strategy is legal, priced right, and worth your time.
Rule these out
The two markets your answers argue against.
How this was sourced, and what we could not verify
Every regulatory position above was read from the governing jurisdiction's own published material — city fact sheets and code-compliance pages, county zoning division statements, land development codes, council minutes, and Osceola County's official list of subdivisions approved for short-term rental. Market figures come from the Orlando Regional REALTOR Association (July 2026), Redfin submarket data (June 2026), Zillow and Yardi rent indices (July–August 2026), AirDNA and AirROI vacation-rental data (trailing twelve months to mid-2026), Freddie Mac's rate survey, and county property appraiser and tax collector millage schedules for the 2025 tax year.
State law, as of September 1, 2026. Florida Statute 509.032(7)(b) bars a local ordinance from prohibiting vacation rentals or regulating their duration or frequency — but it exempts any ordinance adopted on or before June 1, 2011. SB 280 (2024) passed the Legislature and was vetoed. No successor preemption bill became law in the 2025 or 2026 sessions; the 2026 vacation-rental bills concerned pool safety and died in the House.
What we could not confirm, and would not guess at:
- Maitland. The city's adopted Land Development Code confirms a Short-Term Rental Unit Certificate exists. The owner-occupancy requirement itself we read from a third-party code mirror rather than the official text, and we could not reach the city's fee schedule. Confirm with Maitland Community Development at (407) 539-6211.
- Town of Windermere. We found no short-term rental provision anywhere in the town's readable material. That is not the same as confirming the town permits one. Ask the town directly, and confirm from the Property Appraiser record whether the parcel is even inside town limits.
- City of Clermont and City of Minneola. Both are building vacation rental registration frameworks — Minneola's council adopted registration fees in November 2025, matching Clermont's — but neither city's actual rules were readable. What is confirmed is that registration exists, not what it permits.
- City of Winter Garden and City of Davenport publish no readable short-term rental provision. We make no claim about either.
- Whether the prohibitions in Orange County and Winter Park pre-date June 1, 2011 — and are therefore insulated from state preemption — could not be established. Both currently assert and enforce them, so treat them as binding, but the grandfathering question is not settled.
- Osceola County's approved-subdivision list is dated May 2022 and carries the county's own disclaimer as to accuracy. Storey Lake, Solterra and Windsor Island are widely marketed as short-term rental communities; we confirmed only ChampionsGate and Reunion against a government record.
- Community Development District figures are practitioner estimates. Verify against the actual tax bill for the specific parcel.
Two things private documents can do that zoning cannot. State preemption limits local government, not private covenants. Under Florida Statute 720.306(1)(h), a homeowners' association may amend its documents to prohibit rentals of under six months and limit rentals to three times a year, and that amendment binds every parcel owner — including existing owners who did not consent. Condominium owners have stronger protection: Statute 718.110(13) applies such an amendment only to owners who consent or who buy afterward. In an ordinary HOA subdivision, the association voting out short-term rental is the single largest non-zoning risk to the investment.