Is Windsor Hills a good vacation rental investment?

Windsor Hills is one of the most established and closest STR-approved communities to Disney World (about 2 miles). The HOA fully supports vacation rentals — the community was built around the STR model. Nightly rates range $150–$400 depending on bedroom count, with 77%+ occupancy achievable. The main consideration is that much of the inventory dates to the early 2000s, so factor renovation costs into acquisition.

What county is Windsor Hills in and what are the STR rules?

Windsor Hills is in Osceola County (zip 34747) within the county's STR Overlay District. You need a Florida DBPR Vacation Rental license (~$170/year) plus an Osceola County STR license ($250 + $160 inspection). Combined tax rate is 13.5%. The HOA permits and supports short-term rentals.

How far is Windsor Hills from Disney World?

Windsor Hills is approximately 2 miles from the Walt Disney World entrance — one of the closest STR-approved communities to the parks. This proximity is a major driver of its consistent occupancy and is heavily featured in property marketing.

Vacation Rental Communities/Windsor Hills

Community Guide · Osceola County

Windsor Hills Resort Investment Guide

One of the closest STR-approved communities to Disney World — just ~2 miles from the entrance. Windsor Hills was purpose-built for vacation rental, with an HOA that fully supports short-term rentals. Here's the complete investor picture.

~2 mi

To Disney

$150–400

Nightly Rate

77%+

Occupancy

13.5%

Tax Rate

Find Windsor Hills Properties

The Community

Why Windsor Hills

Windsor Hills Resort is one of the oldest and most established vacation rental communities in the Disney corridor. It was developed in the early-to-mid 2000s specifically as a short-term rental community — the HOA structure, amenities, and zoning were all built around the vacation rental model.

The community offers a mix of condos, townhomes, and single-family pool homes ranging from 2 to 6 bedrooms. Resort amenities include a large pool with water slide, fitness center, theater, game room, and clubhouse — all of which drive nightly rate premiums and guest satisfaction.

The proximity to Disney (~2 miles) is the headline. Few STR-approved communities are this close to the parks, and it's the single most marketed feature for guests booking Windsor Hills properties.

Investor Considerations

What to Know Before Buying

Aging Inventory

Much of Windsor Hills was built 2004–2008. Properties that haven't been renovated may need $30–60K in updates to compete with newer resort communities like Storey Lake and Reunion. Factor this into your acquisition math.

HOA Supports STR

Unlike many communities, Windsor Hills' HOA actively supports short-term rentals. This eliminates the #1 risk in STR investing — post-purchase HOA prohibition. Still review current CC&Rs for any minimum-stay or operational rules.

Established Guest Base

The community has 20+ years of guest reviews and repeat bookings. A well-maintained property with strong reviews can stabilize occupancy faster than a brand-new community with no track record.

Competition From Newer Resorts

Windsor Hills competes with newer amenity-rich communities. Properties without updated interiors and modern amenities may see rate pressure. Renovation is often the value-add lever here.

Example Returns — 4BR Pool Home

Purchase Price (renovated 4BR)$430,000

Avg Nightly Rate$240

Annual Occupancy (conservative)72%

Gross Revenue$63,072

Management (25%) + HOA−$21,600

Taxes (13.5%)−$8,515

Maintenance, Utilities, Supplies−$7,500

Annual NOI$25,457

Cash-on-Cash (cash buyer)5.9%

At 80% OccupancyNOI ~$33K / 7.7% CoC

Illustrative model. Actual returns depend on property condition, management quality, and seasonal pricing strategy. The renovation lever (updating a dated property) is often the strongest return driver in Windsor Hills.

All STR-Approved Communities →Solterra Resort Guide →Reunion Resort Guide →STR Cap Rates →STR Financing →

Interested in Windsor Hills?

We'll find Windsor Hills properties matching your budget, verify the renovation needs, and confirm current HOA rules before you make an offer.

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