The Pickle
Almost every vacation home for sale in Florida is marketed as a short-term rental. A meaningful share of them can't legally be rented nightly, and plenty of the rest don't cover their own carrying costs.
The trouble is timing. In a standard purchase, the association and condo documents show up after you've signed a contract, and rental eligibility gets taken from a field on the MLS that the listing agent filled in. By the time anyone reads the fine print, you're emotionally — and sometimes financially — committed.
I do it the other way round. I read the zoning, the recorded declaration, the condo financials and the real numbers first, and I only put homes in front of you that pass. My company cleans, maintains and manages hundreds of vacation homes, so I know what these properties actually earn and actually cost.
Rental eligibility is decided parcel by parcel — never by the listing.
What Gets Checked
Nothing on the left is wrong — it's just not enough for a home that has to earn its keep.
| The question | A standard transaction | With me |
|---|---|---|
| Can it legally be rented nightly? | Taken from the MLS rental field, which the listing agent fills in | Checked against county/city zoning and the recorded association declaration — stricter wins |
| Association & condo documents | Delivered during the review period; reading them is left to you | Read before you offer: lease minimums, leases-per-year caps, registration fees, approval rules, pet and parking rules |
| Condo financial health | Monthly dues quoted | Budget, reserves, structural reserve study, milestone inspection status, pending special assessments and litigation |
| Licensing & tourist tax | Not discussed | State lodging licence, county/city registration, and the tourist-tax accounts you'll have to open |
| True monthly carrying cost | Mortgage estimate from a listing site | HOA + CDD + taxes after reassessment + insurance + utilities + cleaning — before the mortgage |
| Income | The seller's projection or a brochure number | Comparable-home market data and a break-even occupancy you can check against last year |
| Insurance & flood | A lender placeholder | Flood zone, a real quote, roof age, wind mitigation — before you're under contract |
| Condition | Your inspector, after you're committed | Roof, AC, water heater and pool judged by people whose crews repair them, before you offer |
The Due-Diligence Review
Every property I recommend has been through these. You get the findings in writing, with the source documents, so you and your attorney can verify every line.
Is transient (under 30-day) occupancy a permitted use at that exact address under the county or city code?
Minimum lease terms, caps on leases per year, rental registration, guest approval and any amendment in progress that would change them.
Florida DBPR lodging licence, local STR registration or business tax receipt, and state plus county tourist-tax accounts.
Reserves, the structural reserve study and milestone inspection where they apply, recent and pending special assessments, litigation.
Dues, CDD, taxes after reassessment, insurance, utilities, pool and pest — a monthly number before the mortgage.
What comparable homes actually earned, not what the listing says. The occupancy you need to break even, next to what the market achieved.
Flood zone and elevation, a real quote, roof age and wind mitigation — the numbers that most often move the payment.
Remaining life and local replacement cost of roof, AC, water heater and pool equipment.
Furniture, bookings on the calendar, the listing itself (it usually doesn't transfer), and who owns the smart locks and linens.
Who buys it from you in five years, and whether a rule change would shrink that buyer pool.
Three Markets
Each market has its own rulebook and its own traps. The review changes with it.
Orlando · Kissimmee · Davenport · ChampionsGate · Reunion
The Disney corridor. Purpose-built resort communities where nightly rental is the point — next to look-alike subdivisions where it's prohibited. CDD bonds, resort fees and master-association rules are where the surprises live. My service company works inside these communities every day.
See an example →Cocoa Beach · Satellite Beach · Melbourne Beach · Indialantic
Much of the inventory is condos, and condo documents decide everything: many buildings set 30-day or longer minimums, and some beach cities limit nightly rentals in residential zones. Older oceanfront buildings also face Florida's newer structural-inspection and reserve requirements, which is where special assessments come from.
See an example →St. Pete Beach · Clearwater · Madeira Beach · Indian Rocks
Beach-town rules vary city by city, and after the 2024 storms the flood questions matter more than ever: elevation, prior damage, and whether a home in the flood zone would be limited in what could be rebuilt under the substantial-improvement rule. Great rental demand — on the right parcel.
Why It Matters
These are the problems I look for on every vacation-home purchase — each one turns a “good deal” into a monthly bill.
How It Works
Budget, loan type, how many weeks you want for yourself, and the monthly number the home has to clear. That decides the region and the communities before we look at a single house.
On-market listings plus homes I hear about early through the management side of my business. Anything that fails the rental rules or the numbers never reaches you.
Each property comes with its findings: what the documents allow, the monthly carrying cost, realistic income and break-even occupancy.
Offer strategy grounded in the real numbers, an inspection read by people who fix these systems, and a remote closing if you need one.
Cleaning, maintenance and setup through my service company if you want it — or I'll introduce you to whoever you choose. Either way, you're not starting from zero.
Free Listing Check
Found a vacation home on Zillow, the MLS or a friend's text? Send it over. I'll come back with whether it can legally be rented the way you plan, what it really costs to carry each month, and whether the numbers hold up — or why I'd walk.
No agreement required, and it's fine if you're already working with another agent.
