Furnished rentals · 30 days and up · Kissimmee
Mid-Term Rental Management in Kissimmee, FL
Furnished stays of a month or more — snowbird seasons, travelling professionals, relocations and insurance placements — found, screened and looked after by our own team.
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Step 1 of 4 · Address
What’s the address of your property?
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Kissimmee, FL
Why Kissimmee — and what it means for your property
Kissimmee is the address on most Disney-area vacation homes, but two rulebooks apply: the city's overlay inside city limits and Osceola County's overlay outside them. We check which one before we list.
Kissimmee sits in Osceola County, which sets much of the regulatory and tax picture for property here. We track those rules per address rather than per city, because they rarely stop neatly at a city line.
What stands out about Kissimmee
- City rentals under 30 days need the Short-Term Rental Overlay (STRO)
- Unincorporated Kissimmee addresses follow Osceola County's overlay rules
- Osceola County's 6% tourist tax is paid to the county Tax Collector
- Kissimmee Gateway Airport and HCA Florida Osceola Hospital in town
- Short, mid-term and long-term rental management from one team
How mid-term rental management works in Kissimmee
What mid-term rental management is
A mid-term rental is a furnished home let for a month or more at a time — longer than a vacation stay, shorter than a year’s lease. It suits guests who need a real home for a while: snowbirds spending the winter, travelling healthcare staff on contract, families relocating for work, and households placed by their insurer after a fire, flood or storm.
For owners it means fewer turnovers, less wear and steadier occupancy than nightly hosting. We price it, find and screen the guests, put a written agreement in place, and look after the home and the guest for the whole stay — with our own cleaning and maintenance staff.
Why mid-term works so well in Florida
Florida has a built-in monthly market: winter residents who come for one to six months every year, plus a steady flow of contract professionals and relocating families. A furnished home in the right place can fill its winter with one or two long stays instead of dozens of short ones.
Monthly stays are also an option for many owners whose condo association or neighbourhood rules limit nightly rentals but allow longer ones — check your documents, or send them to us and we will.
What mid-term rental management looks like in Kissimmee specifically
For a Kissimmee home inside city limits but outside the Short-Term Rental Overlay, stays of 30 days or more are the main way to rent furnished, because Code §14-6-44 only prohibits rentals of less than 30 days in residential districts. We set those homes up with monthly minimums from day one.
Medical stays are a natural fit. HCA Florida Osceola Hospital is at 700 West Oak Street in Kissimmee, and clinicians on assignment and patients' families often need a furnished home for a month or more. Stays of six months or less still owe Osceola County's 6% tourist development tax, so we collect and remit it on those bookings too.
Want the whole property handled, not just mid-term rental management? Kissimmee property management covers short-term, long-term and everything between — one team, one point of contact.
Free projection · Kissimmee
What could your Kissimmee property earn?
Send us the address and we'll come back with real numbers for it, using actual Kissimmee data — from a person on our team, within one business day.
Free, no obligation. Prefer to talk? Call (321) 321-2348
Step 1 of 4 · Address
What’s the address of your property?
We’ll pull real, comparable Florida listings to build your projection.
Included in Kissimmee
One rate. The whole service.
Quoted for your property, in writing, before you sign anything.
- Pricing by the month and the season
- Listings on the platforms monthly guests use
- Guest screening and a written rental agreement
- Move-in ready furnishing advice and set-up
- Mid-stay check-ins and guest support
- Cleaning between stays by our own teams
- Maintenance by our own staff throughout the stay
- Utilities and amenities kept in order
- Monthly statements and payouts
Kissimmee questions
Owning and renting in Kissimmee
Is Airbnb legal in Kissimmee?
Yes, in the right place. Inside city limits, Kissimmee Code §14-6-44 prohibits renting a dwelling for less than 30 days in a residential district unless it sits in the Short-Term Rental Overlay (STRO) and was approved for short-term use in an SRPUD or MUPUD, or as a conditional use. Many homes with a Kissimmee mailing address are in unincorporated Osceola County, where short-term rental is allowed only in a Planned Development inside the county's Short-Term Rental Overlay (LDC 3.12.2).
What taxes apply to short-term rentals in Kissimmee?
Stays of six months or less owe Florida's 6% sales tax (§212.03), Osceola County's 1.5% discretionary sales surtax (DOR form DR-15DSS) and Osceola County's 6% tourist development tax (DOR form DR-15TDT, R. 10/26; Osceola Code §13-61). The tourist tax is collected by the county, and the Osceola County Tax Collector says it is not contracted with Airbnb, VRBO or other platforms, so owners or their managers remit it.
Do you also manage long-term rentals in Kissimmee?
Yes. Homes outside an approved overlay can still earn as furnished stays of 30 days or more or as annual leases, which we run with licensed broker partners handling the leasing.
Other services in Kissimmee
Mid-Term Rental Management nearby
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