999: How a 16-Unit Idea Became One of America’s Largest Resort Experiences

Westgate didn’t just build a resort — they built a small city of experiences.

In this walking-tour episode, Glenn Haussman explores Westgate Vacation Villas in Orlando with Chief Business & Strategy Officer Jared Saft, starting at the original 16-unit building from the early 1980s and moving through the resort’s huge renovation and expansion.

We visit the movie theater, the retail experiences designed by Starboard, the Chuck E. Cheese–powered arcade, the toddler zone, the retro arcade, the Mystery Funhouse throwbacks, the in-lobby candy shop with a waterslide running through it, and the multi-level Shipwreck Island Waterpark.

Jared also shares how Westgate plans new concepts, how they think about every family member’s experience, and what’s next as they just added 40 new destinations during a major growth cycle.

This episode is brought to you by Actabl — Actabl gives you the power to profit. Visit Actabl.com.

What we cover:

🏨: The origin story — from a 16-unit project to one of Florida’s largest resorts

🎬: How the in-lobby movie theater reduces check-in stress for families

👾: The Mystery Funhouse legacy and why nostalgia still excites kids

🍭: The ice-cream + donut + candy shop with a water slide running overhead

🌊: Shipwreck Island Waterpark, lazy rivers, and multi-level amenities

🍽️: How Westgate approaches F&B for families with mixed tastes

🚀: Westgate’s expansion strategy and why they act like entrepreneurs, not a big-box brand

Your turn:

What feature would make you choose one family resort over another?