Is Windsor at Westside Good for Airbnb Investment in 2026?

Windsor at Westside has emerged as one of the standout resort communities in the Kissimmee short term rental market. With strong amenities, a Kissimmee location, and explicit STR permissions in the governing documents, it attracts consistent investor and guest interest. Here is what you need to know.

What Is Windsor at Westside?

Windsor at Westside is a gated resort community in Kissimmee, Osceola County, located on Westside Blvd near the US-192 and US-27 corridor. The community features a clubhouse with a resort-style pool, lazy river, waterslide, splash pad, fitness centre, games room, sports courts, and on-site food and beverage service. Properties range from townhomes to large single-family homes up to fourteen bedrooms, all with private pools.

Windsor at Westside is purpose-built for vacation rentals and is part of the established Windsor brand of resort communities with a strong track record in the Central Florida market.

STR Performance at Windsor at Westside

Windsor at Westside competes directly with Solara, Storey Lake, and ChampionsGate for the mid-to-premium family vacation market.

Large homes are the top performers. The community's ability to host ten to fourteen bedroom properties makes it particularly attractive for the large group and multi-family segment — the highest-revenue guest profile in the Disney corridor. These are the bookings where nightly rates of $500 to $1,200 or more per night are achievable for the right property.

Brand recognition helps conversion. The Windsor brand carries weight with repeat visitors to Central Florida, which can benefit direct booking rates and repeat guest bookings compared to newer or less established communities.

Mid-size homes provide solid consistent returns. Five to seven bedroom homes at Windsor at Westside typically generate $65,000 to $100,000 annually under professional management. Larger homes push significantly higher.

HOA and Compliance

Windsor at Westside is in Osceola County — DBPR license, Osceola County STR registration, and approximately 12% combined tourist development and sales tax apply. Edge handles all compliance for Windsor at Westside property owners.

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