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Windsor at Westside Resort Vacation Rentals in Orlando

A gated resort in Kissimmee centered on a 10,000 sq ft clubhouse with a zero-entry pool, lazy river, water slide and hot tub. Homes sleep up to 20+ guests.

Windsor at Westside Resort Amenities

Spacious vacation homes with private pools, themed bedrooms and full access to the 10,000 sq ft clubhouse.

Explore Windsor at Westside Resort

Clubhouse Amenity

Resort Pool & Lazy River

Clubhouse Amenity

Clubhouse & Tiki Bar

Vacation Rentals

Private Pool Homes

Get more when you book direct

Lower prices, every time

Pay less than you would anywhere else. No middlemen or platform fees.

Direct line, real care

Book with the team that actually runs the property. Faster answers, better service, real accountability.

Not just a transaction

We go further for direct guests. We’re building a relationship, not closing a booking.

Windsor at Westside Resort FAQ