| HOA dues | ≈$354–$367 / monthUnconfirmed — verify with the associationListing and association data, via VHG Resort Cost Index · verified Aug 2026 |
|---|---|
| CDD assessment | NoneNo district assessment on the tax bill.County tax roll, via VHG Resort Cost Index · verified Aug 2026 |
| Minimum lease term | 3-night minimumNo one-night stays. Long-term leases of 6+ months are also permitted. This is a real constraint on shoulder-season fill and on last-minute single-night demand.Community policy documents, via VHG community research · verified Aug 2026 |
| Short-term rental position | Permitted, with the 3-night floorNo on-site rental desk — you arrange your own management.Osceola zoning + association documents · verified Aug 2026 |
| Combined lodging tax | 13.5% combinedOwner self-remits the 6% tourist development tax monthly.Osceola County Tax Collector + Florida DOR · verified Aug 2026 |
| Nightly rate (market proxy) | ≈$200–$290 / night (market)Unconfirmed — verify with the associationMarket-level proxy, not a measured community set.AirROI Kissimmee market TTM · mid-2026 |
| Occupancy (market proxy) | 45–55%Unconfirmed — verify with the associationKissimmee market range across providers · mid-2026 |
Windsor Palms is one of the cheapest genuine ways into an Osceola resort community with no district assessment — dues in the mid-$350s and condos from around $205,000. On carrying cost alone it is among the most efficient properties in this guide.
The rule that shapes everything is the three-night minimum stay. It is not a manager’s policy you can change; it is the community’s. That removes one- and two-night bookings entirely, which matters most in shoulder season when short-stay demand is what fills a calendar. It also means fewer turnovers per booked night, which cuts your cleaning cost — so it is genuinely a trade rather than simply a cost.
There is no on-site rental desk, so you arrange your own management or self-manage. That is freedom if you have a manager you trust and a burden if you do not.
Figures are current as of the dates shown and change. The HOA figure could not be confirmed from a primary source. Confirm the minimum-stay rule in the recorded documents before underwriting any strategy that depends on it.