Windsor Palms

Windsor Palms was developed by Pulte Homes and built between 2000 and 2003 on land off US-192 in Kissimmee, approximately 2.5 miles from the Walt Disney World main entrance. The community was originally named Wyndham Palms, but the name was changed early in its history following trademark conflicts with Wyndham Resorts. The original Pulte construction established the community's footprint: single-family homes and townhomes clustered around a central clubhouse, with a gated perimeter designed from the outset to support both owner-occupied residency and short-term vacation rental use.

The community's structure reflects the particular demands of the Orlando vacation home market circa 2000 — professionally managed resort amenities, shuttle service to theme parks, and deed allowances permitting rentals as short as three nights. This made Windsor Palms one of the first established communities in the Kissimmee STR corridor to combine resort resort club infrastructure with private ownership, rather than the timeshare or hotel model that otherwise dominated the Disney-adjacent market.

Over the subsequent two decades Windsor Palms has matured into one of the better-known STR community addresses in the Kissimmee market. The original Pulte construction is now 20-plus years old, meaning buyers encounter a wide range of home conditions — from units that have been in active short-term rental service with corresponding wear, to owner-occupied primary residences that have been extensively updated. The community's proximity to Disney, Universal, and SeaWorld remains its defining asset and the primary driver of rental income underwriting.