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A short-term rental buyer's guide to Windsor Hills, off N Old Lake Wilson Rd, just south of US-192.
By Paul Kim, REALTOR®, Norkis & Co Realty · Last reviewed October 29, 2026
Yes. Windsor Hills is one of the established short-term rental resorts near Disney, and current listings in all three of its associations (The Enclave homes, The Vistas townhomes, and The Ventura condos) show no minimum stay and no association approval for rentals. It's also the closest of the resort communities we cover to the Disney parks: 8 to 18 minutes. Confirm the specific association's rules before you buy, since some listings note that long-term rentals may be restricted.
STR suitability: B (3.85 out of 5)
How suitable Windsor Hills is for running a short-term rental. It is not a prediction of income. How we grade.
Zoning: Osceola County's official Short Term Rental Listing includes Windsor Hills, Bunker Hill (Windsor Hills), and The Ventura at Windsor Hills, meaning they sit in the county's short-term rental area. Verified
Checked against Osceola County STR Listing (entries 24, 245), document revised 2022-05. Verified October 29, 2026. The county list was last revised May 2022. Confirm the parcel with Osceola County Zoning (407-742-0200).
County: Windsor Hills is in Osceola County, with a Kissimmee address. It's on the county's short-term rental list and is not in a Community Development District, so there's no CDD charge on the tax bill. Verified
Sources: Osceola County STR Listing (entries 24, 245) · Osceola County CDD list
| Rule | What it is | What it means for you |
|---|---|---|
| Osceola County zoning | Listed in Osceola's short-term rental area (entries 24 and 245). Zoning code being confirmed with the county. | Green lightNo county restrictions on short-term rentals here. Source |
| HOA rules | HOAs have their own rules, separate from county and state law. | Check thisEven where the county allows short-term rentals, an HOA can restrict or ban them in its area, and can change its rules later. Check the HOA's rules before you buy. Source |
| Florida DBPR vacation rental license | State license required for every short-term rental. | About $230 the first year, then about $180 a year to renew. Source |
| Osceola County business tax receipt | County business license for your rental, issued by the Osceola Tax Collector. Applications go through zoning, environmental health, and building review. | Apply with your state license (or its application). About $30 a year, renewed July 1 to September 30. Letting it lapse can cost you your zoning approval. Source |
| Florida sales tax | 7.5% on every stay in Osceola: 6% state sales tax plus Osceola's 1.5% county surtax. | Airbnb collects and pays this on its bookings. Direct bookings are yours to file. With the 6% tourist tax, guests pay 13.5% in total. Source |
| Osceola tourist development tax (6%) | County tax on short-term rentals, separate from Florida sales tax. | Check thisOsceola doesn't let booking sites collect and pay this tax for owners. You'll have to collect and pay it yourself on every booking, on every channel. Source |
Costs, deadlines, and the order to file in: Florida STR licenses and taxes.
| Section | Short-term rentals | Notes |
|---|---|---|
| The Enclave (single-family homes)Reported | Allowed | Current listings show no minimum stay (or 1–7 days), no lease restrictions, and no association approval for rentals. Sources: Stellar MLS listing data (Oct 2026) · Windsor Hills Master Association |
| The Vistas (townhomes)Reported | Allowed | Current listings show a 1–7 day minimum stay and no association approval. The Vistas appears to have its own management company. Not the same community as The Vistas at ChampionsGate. Sources: Stellar MLS listing data (Oct 2026) · Windsor Hills Master Association |
| The Ventura (condos)Reported | Allowed | Current listings show no minimum stay, no lease restrictions, and no association approval, and are marketed as short-term rentals. Sources: Stellar MLS listing data (Oct 2026) · Windsor Hills Master Association |
| Section | Charge | Amount | What it covers |
|---|---|---|---|
| All of Windsor Hills | Windsor Hills Master AssociationReported | $1,202.99 / quarter | Gate, clubhouse, pool, courts, roads, and basic cable and Wi-Fi, per listings. About $401 a month. Stellar MLS listing data (Oct 2026); being confirmed with the association |
Every Windsor Hills home pays the master association plus its own sub-association. There is no CDD. Fee amounts are being confirmed with the associations before publishing.
Sources: Stellar MLS listing data (Oct 2026)
| Destination | Typical drive | Distance |
|---|---|---|
| Theme parks | ||
| Magic Kingdom | 10–18 min | 6.8 mi |
| EPCOT | 10–18 min | 6.3 mi |
| Hollywood Studios | 9–16 min | 5.3 mi |
| Animal Kingdom | 8–18 min | 3.5 mi |
| Universal Studios Florida | 24–45 min | 15.4 mi |
| Universal Epic Universe | 24–45 min | 14.7 mi |
| SeaWorld Orlando | 20–40 min | 11.5 mi |
| LEGOLAND Florida | 40 min–1 hr 15 min | 32.3 mi |
| Sports, events, and travel | ||
| ESPN Wide World of Sports | 9–16 min | 5 mi |
| Orange County Convention Center | 20–40 min | 11.9 mi |
| Orlando International Airport (MCO) | 24–40 min | 22.2 mi |
| Golf | ||
| ChampionsGate Golf Club | 12–18 min | 7 mi |
| Reunion Resort & Golf Club | 12–16 min | 5.3 mi |
| Waldorf Astoria Golf Club | 14–28 min | 7.8 mi |
| Providence Golf Club | 20–35 min | 10.7 mi |
| Grand Cypress Golf | 20–30 min | 11.2 mi |
| Shingle Creek Golf Club | 24–45 min | 14 mi |
| Orange County National | 18–24 min | 14.1 mi |
| Arnold Palmer's Bay Hill Club & Lodge | 26–55 min | 14.4 mi |
| Southern Dunes Golf & Country Club | 26–45 min | 18 mi |
| The Club at Bella Collina | 40–50 min | 34.4 mi |
| Mission Resort + Club | 50 min–1 hr | 49.7 mi |
| Streamsong Golf Resort | 1 hr 10 min–1 hr 40 min | 66.5 mi |
| Cruise ports | ||
| Port Tampa Bay | 1 hr–1 hr 15 min | 64.1 mi |
| Port Canaveral | 1 hr–1 hr 25 min | 67.5 mi |
| PortMiami | 3 hr 20 min–4 hr 20 min | 235 mi |
| Beaches and day trips | ||
| Kennedy Space Center Visitor Complex | 1 hr 5 min–1 hr 30 min | 65.7 mi |
| Cocoa Beach Pier | 1 hr 5 min–1 hr 40 min | 69.8 mi |
| Clearwater Beach (Pier 60) | 1 hr 30 min–2 hr 20 min | 88.1 mi |
| Daytona Beach Boardwalk | 1 hr 20 min–2 hr 10 min | 79.4 mi |
| Cities | ||
| Downtown Tampa | 1 hr–1 hr 15 min | 64.5 mi |
| Downtown Miami | 3 hr 20 min–4 hr 20 min | 234 mi |
Measured on Google Maps from Windsor Hills Resort clubhouse (2600 N Old Lake Wilson Rd): fastest route, typical traffic, departing Tuesday 10:00 AM. Measured October 28, 2026.
The mistakes that cost owners here money, and how to avoid them.
In Osceola County it doesn't. The county is not contracted with Airbnb, VRBO, or any booking platform for its 6% tourist development tax, so the owner or manager has to collect and remit it on every booking.
Sources: Osceola County Tax Collector
Windsor Hills is close enough to Disney that a lot of its listings lean on Disney-themed bedrooms and character murals. When half the resort has a Mickey room, a Mickey room isn't a reason to book yours. The listings that stand out are built around a specific trip, not a decor theme.
Most Windsor Hills homes were built between 2004 and 2010 and have hosted guests for much of that time. Roofs, AC systems, pool equipment, and water heaters are at or near replacement age, and furnishings wear faster under constant turnover. Inspect for it and budget for it before you make the offer.
Sources: Stellar MLS listing data (Oct 2026)
Windsor Hills bills its master association quarterly, and listings mix monthly, quarterly, and annual figures in the same fields. We've seen the same master fee entered as $1,202.99, an older $1,117.97, and folded into an annual total. Get the estoppel letter and convert everything to the same period before you run the numbers.
Sources: Stellar MLS listing data (Oct 2026)
Osceola ties your rental's zoning approval to your short-term rental business tax receipt. The receipt costs about $30 a year and renews between July 1 and September 30.
Sources: Osceola County Tax Collector
Florida law lets an HOA amend its rules to prohibit rentals shorter than six months, or to cap rentals at three per year, and that kind of amendment applies to every owner, including people who bought before the vote.
Sources: Fla. Stat. 720.306(1)(h)
Windsor Hills is about proximity. It's the closest of the resort communities we cover to the Disney parks, which makes it the natural base for park-heavy trips.
Why the concept matters more than the community: Concept, not theme.
We don't publish occupancy or income for individual communities. What a rental earns depends far more on its concept, its execution, and its location within the community than on the community's name.
| Criterion | Score | Why |
|---|---|---|
| Regulatory certainty | 4/5 | On the county's STR list, and listings in all three associations show short-term rentals permitted with no approval. Being confirmed against the associations' governing documents. |
| HOA rental friendliness | 5/5 | No minimum stay and no association approval in any association, per current listings. |
| Cost burden | 4/5 | No CDD, and the master association runs about $401 a month. Sub-association fees being confirmed. |
| Guest draw | 3/5 | Clubhouse, pool, fitness center, theater, and game room. Solid, but smaller than the water-park-style clubs at newer resorts. |
| Location | 5/5 | 8–18 minutes to all four Disney parks and 9–16 to ESPN Wide World of Sports. |
| Competition & differentiation | 2/5 | An established resort full of similar, heavily themed rentals; differentiation has to come from the home. |
Weighted per our published rubric. Overall 3.85/5 → B.
Want the current list, filtered to the villages that actually allow short-term rentals?
I'll send it, with the HOA and CDD numbers for each.
Yes. Current listings in all three associations, The Enclave, The Vistas, and The Ventura, show short-term rentals permitted with no minimum stay and no association approval. It's on Osceola County's short-term rental list.
8 to 18 minutes to all four Disney parks, measured on Google Maps with typical traffic on a Tuesday morning.
No. Windsor Hills is not on Osceola County's list of Community Development Districts, so there's no CDD assessment on the tax bill.
No. Osceola County is not contracted with any booking platform for its 6% tourist development tax, so owners or their managers must collect and remit it.