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Regulation & tax

The rules are the complicated part.
That's the part we do.

Short-term rental laws are written street by street, they contradict each other, and they change. Knowing what a specific parcel is permitted to do — today — is a job, and it's the one we're best at.

Check An Address Rules By Market
Free, instant

Start with the only question that has a definite answer

Which jurisdiction your property is legally in. Not the one on your post — a Clearwater mailing address can sit inside Largo, under a different rulebook entirely. This reads the county's own boundary data and answers on the spot.

The jurisdiction is instant in Pinellas, Polk and Hillsborough. We confirm the short-term rental rules jurisdiction by jurisdiction, against each one's own material rather than a published guide. Every Pinellas jurisdiction is done; in Polk and Hillsborough we are working through them now, and where we haven't confirmed one yet we will say so and email you the rules as soon as we have them. Put in an address in one of the other markets we work in and we will research it the same way by hand. Anywhere else, we will tell you so plainly rather than take your details and go quiet.

The town on the mail is fine — we only use it to find the parcel, never to decide the rules. Spelling doesn't have to be perfect.

Where the rules themselves arrive. The jurisdiction shows on screen either way.

We'll only use this to answer your question. No list, no drip campaign, no passing your details to anyone.

On screen, straight awayThe jurisdiction your parcel is legally in, read from the county's boundary layer rather than the postal city.
Then the rules, by emailWhat that jurisdiction actually permits, and whether nightly is on the table there at all.
Free, and no obligationPlenty of these end with us telling an owner not to buy. We would rather say it now than after you have.

Almost everywhere worth renting is regulated now

Minimum stays, registration certificates, safety inspections, occupancy caps, parking ratios, quiet hours, tourist development tax, and association bylaws that can override the city entirely. A destination without rules is mostly a destination that hasn't written them yet.

And it is all set municipally — not by the state, not even by the county. Pinellas describes itself as “a unique mix of 25 governmental bodies”: twenty-five separate rulebooks, in a county you can drive end to end in under an hour. Two properties a mile apart routinely sit under completely different regimes.

Nightly rentals restricted or prohibited in residential zones Nightly rentals genuinely workable

Illustrative, and not a map — the tiles aren't in any geographic order and we're not labelling them. The point is the proportion, and that nothing about a property's address tells you which tile it's in.

And they move. In March 2025 Pinellas County adopted a short-term rental ordinance that hadn't existed the year before — certificates, inspections, occupancy caps, an annual fee — and gave owners a three-month window to comply, staggered by ZIP code.

The answer changed for some Pinellas owners and not for others, on the same day. Nobody sent the ones it changed for a letter.

Twenty-three years of Pinellas rule changes, in four dates
2003 Clearwater sets a thirty-one-day minimum

Ordinance 7105-03. Still the rule in standard residential zones more than twenty years later — and still news to owners who bought last year.

March 2025 The county writes a rulebook that didn't exist

Certificate of Use, safety inspection, occupancy cap, parking minimums, quiet hours, $450 a year — for the unincorporated county only.

31 May to 31 July 2025 A three-month window, staggered by ZIP code

Different deadlines for different owners, based on where the property sits. Miss yours and the calendar you'd already taken bookings on is what's at risk.

Next Nobody knows, and that's the job

Twenty-five jurisdictions, each free to change its mind, none of them obliged to tell you. Somebody has to be watching.

This is the part we are actually qualified for

Natalie is a professional urban planner — a master's in urban planning, and years working with developers to get large condominium, commercial, industrial and subdivision projects through approval. Reading a zoning code, working out which body genuinely has authority over a parcel, and getting a written answer out of a planning department is not something we picked up along the way. It is the job she trained for.

Most short-term rental managers are operators who learned the rules because they had to. We came at it from the other end. Let us take care of the planning and the regulation side of it.

What tracking the rules actually involves

This is the part of the business that quietly eats owners: not the cleaning, not the guests — the tracking. Which authority actually has jurisdiction over your parcel, what it permits today, what it's about to permit, which renewal is due, and what your association's documents say on top of all of it.

Five kinds of Clearwater property can rent nightly. Most of their owners don't know it.

The City of Clearwater requires a minimum stay of thirty-one days in standard residential zones. That much is widely known, and most owners stop there — they read “Clearwater” and “thirty-one days” and conclude the door is shut.

It isn't, for everyone. There are five distinct categories of Clearwater property that are legally free to rent nightly, and we have them mapped. The owners inside those categories are frequently the last to find out: running thirty-one-day minimums they don't need to run, or not renting at all, on a property that is permitted to do considerably better.

If you own in Clearwater, this is worth ten minutes. Send us the address and we'll tell you free whether your property falls into one of the five. If it does, that is a material change to what your building is worth, and we'd rather you knew.

Find out which category yours is in →

Nightly-capable parcels are the minority in this county, which makes one a genuinely scarce asset. That's also why we're not publishing the list.

Legal doesn't mean profitable

Owners often arrive having established that a property is allowed to be a short-term rental, and treat that as the analysis being finished. It isn't. Permission is not demand, and a legal short-term rental that loses money is still a rental that loses money.

The four things that decide it, none of which are the zoning
The permissive places are the crowded placesWhere the rules are clearly favourable, everybody already knows. Supply gathers there, and your nightly rate is set by the property three doors down rather than by what you paid for yours.
A thirty-one-day minimum is a different business, not a smaller onePlenty of properties can be rented legally — monthly. That's a real business, but it's snowbirds and relocations rather than weekend guests, with different rates, different furnishing and a different season. It also tends not to service a purchase that was underwritten on nightly revenue, which is where owners get hurt.
The costs a rental estimate quietly leaves outCleaning, linen, consumables, licences and receipts, tourist tax, insurance at short-term rates, association fees, higher wear, and a reserve for the year something expensive fails. Online estimators price the top line and stop.
Sometimes the honest answer is an annual tenantFor some properties a long-term lease nets more with a fraction of the work. We'll say so when it's true, even though it's the answer that costs us a management agreement.

So we answer both questions — what a parcel is permitted to do, and whether doing it is worth your money. We'd rather lose the agreement at that stage than have you find out in year two.

Checking an address

The quick answer is free. The one you'd act on isn't.

We used to do the whole thing for nothing, which was pleasant for everyone except us. Now it's split, and the split is honest about which part is a favour and which part is work.

The quick check

Free

Enough to know whether there's anything here at all.

  • Which jurisdiction your parcel is legally in — not the one the mail says. On screen, straight away.
  • That jurisdiction's published short-term rental rules, emailed to you
  • Whether nightly is possible there at all, and what it takes if it is
  • What it can't tell you: your zoning district, your association's rules, or your legal occupancy

No cost, no obligation, and we'll tell you plainly if the answer is no. Plenty of these end with us saying don't buy it. Check an address ↑

The Parcel Report

$149
credited back in full if we manage the property

The written answer for your specific address, dated and sourced.

  • Everything in the quick check
  • The zoning district and the minimum stay that applies to it
  • The full licence, receipt and tax stack, with what each one costs annually
  • Your condominium or HOA governing documents reviewed against it
  • Comparable properties' actual performance, and what you'd net after real costs
  • In writing, dated, with our sources — something you can hand a lender or a partner

The $149 is credited in full against your first month's management fee if the property is placed with us within 90 days of purchase. Most reports take a few days, depending on how quickly the city answers the phone.

Would rather talk to a person first? Ask us about a parcel report → — same report, invoiced.

Why the second one costs money: the answer for one address means confirming the parcel with the Property Appraiser, checking the district against the current zoning map, reading the actual ordinance rather than a summary of it, often calling the planning department and getting the answer in writing, reading your association's recorded declaration, and then pricing the thing honestly. That is a day or two of work and it's the reason people come to us.

Rules by market

Expertise doesn't transfer between counties

Anyone who tells you they know “the Florida rules” is telling you they haven't read them. Each of these markets is a separate body of knowledge. We specialise in Pinellas and Polk; the rest are markets we have owned in, run properties in for other owners, or know because they sit right next door.

Aerial view over a Clearwater condo complex toward the Gulf
Clearwater, Florida Pinellas County Four units we own at the Avalon, plus two homes we owned previously. Twenty-five jurisdictions, and the Clearwater exceptions. Read the Pinellas rules →
Renovated single-storey house in grey and white with new landscaping
Lakeland, Florida Polk County A house we manage for its owner. Approval attaches to the subdivision, not the house. Read the Polk rules →
Snow-covered mountain lodge buildings in Canmore, Alberta with peaks behind
Canmore, Alberta Canmore Owned and operated previously. New Tourist Homes were abolished in 2025, and the conversion window closes 31 December 2026. Read the Canmore rules →
Hillsborough County, FL Tampa, Temple Terrace, Plant City and the unincorporated county. Brandon isn't a jurisdiction. Read the Hillsborough rules → Beaufort County, SC A low-country home we manage for its owner. Ask us about a parcel → Glynn County, GA Brunswick — a property we're setting up now. Ask us about a parcel → Somewhere else? Not the limit of what we'll take on. We'll tell you whether we know the market or would be learning it, before you commit to anything. Tell us where it is →
Then what

Once you know what it can do

Compliance is the first of three things we do. If the answer comes back yes, the next questions are usually whether the place is ready to list and who's going to run it.

Design & Launch → Management →
Start here

Send us the address

The checker at the top of this page gives you the jurisdiction on the spot, and we follow up by email with what that jurisdiction actually permits. If it's worth going further than that, the Parcel Report is the written answer for your specific parcel.

Check Your Address