Westside Cay Homes for Sale

About Westside Cay Neighborhood

Westside Cay is a gated townhome community located in the 34747 zip code of western Kissimmee, situated along the Westside Boulevard corridor between Florence Villa Grove Road and the protected conservation wetlands that buffer the community's southern and western edges. The neighborhood sits within one of Osceola County's most active short-term rental zones, placing residents and investors steps away from the resort-style amenities of neighboring communities and a short drive to the Walt Disney World Resort via SR-429.

The community's townhome-forward design features multi-story, multi-bedroom floor plans that range from approximately 2,100 to 2,200 square feet, offering layouts well suited to both vacation rental operators and full-time Kissimmee residents who want low-maintenance living without sacrificing space. Many homes include private pools — a hallmark of the Westside corridor — along with open-concept kitchens, granite countertops, stainless steel appliances, and paver driveways that reflect the quality standards of the surrounding resort communities.

Conservation land and wetlands along the community's perimeter provide natural buffers that add privacy and Florida wildlife character to the neighborhood. The combination of resort-corridor positioning, private pool homes, gated access, and conservation backdrop makes Westside Cay a distinctive option compared to the higher-density resort communities immediately surrounding it.

The community's location near Westside Boulevard provides straightforward access to US-192 for shopping, dining, and entertainment, while SR-429 enables swift highway-grade travel to Walt Disney World's resort gates, Orlando International Airport, and downtown Orlando without navigating surface streets.

Westside Cay Location & Connections

Westside Cay is positioned along the Westside Boulevard corridor in western Kissimmee, flanked by Florence Villa Grove Road to the north and conservation land and wetlands to the south and west. This location places the community at the center of one of Osceola County's densest clusters of resort communities — directly adjacent to Windsor at Westside, Solara Resort, Murano at Westside, and Magnolia at Westside.

Access to SR-429 (Daniel Webster Western Beltway) makes Walt Disney World reachable in approximately 10 minutes, while US-192 (W. Irlo Bronson Memorial Hwy) along the community's northern edge connects residents to the full stretch of Kissimmee's resort and dining corridor. The surrounding conservation land and wetlands on Westside Cay's south and west perimeter ensure the community maintains a sense of natural separation even within this densely developed resort zone.

Westside Cay Amenities & Lifestyle

Westside Cay benefits from its position at the intersection of Kissimmee's resort corridor and natural conservation land — offering residents a quieter, more private feel within a zone bursting with resort-grade amenities. The Westside corridor is defined by theme park proximity, short-term rental activity, and an evolving dining and entertainment landscape along US-192.

For full-time residents, the community's gated character and conservation backdrop offer a genuine residential atmosphere while the surrounding infrastructure — from grocery and retail anchors along US-192 to the resort amenities of adjacent communities — provides practical day-to-day convenience. Investor-owners benefit from the area's well-established vacation rental market, with strong seasonal demand driven by Walt Disney World visitors year-round.

How Westside Cay Compares

The western Kissimmee resort corridor is filled with options for vacation-home buyers and investors. Westside Cay occupies a specific niche — smaller community scale with gated access, conservation land buffers, and an entry price point that undercuts the larger master-planned resort communities while maintaining the same short-term rental eligibility and Disney proximity.

Compared to the high-density, high-amenity developments nearby, Westside Cay trades a large on-site clubhouse for a quieter, more residential feel — which appeals to buyers who want the investment opportunity without the full resort-community HOA infrastructure and associated fee levels.

Westside Cay HOA & CDD Information

Westside Cay is governed by a homeowners association that oversees gated community access, exterior maintenance standards, and common area upkeep. The HOA structure is consistent with other Westside corridor communities that accommodate both owner-occupied residences and short-term vacation rental operations.

Westside Cay does not carry a Community Development District (CDD) fee — a meaningful financial advantage compared to many competing resort-zone communities in the 34747 zip code. For more information on what CDDs are and how they affect ownership costs, see our CDD guide.

Frequently Asked Questions