Margaritaville Resort Orlando and Windsor Hills both put families near Disney, but they offer very different stays. Margaritaville wraps its cottages in a themed, branded resort. Windsor Hills is a gated vacation-rental community where your home is the main event, whether that’s a condo, a townhouse or a private-pool house, with resort amenities that are there when you want them and out of the way when you don’t.
Location: minutes from the Disney gates
Windsor Hills sits just off Old Lake Wilson Road, immediately south of Walt Disney World and about 2–4 miles from the Disney entrances. Most families are parked at a park roughly 10 minutes after leaving their driveway (see how close Windsor Hills is to Disney). Margaritaville is also close to Disney, along the US-192 dining and entertainment strip, but for park-heavy days, Windsor Hills’ quick run to the gates is hard to beat.
A themed resort vs. a real home base
Margaritaville’s cottages come with a colorful, social, branded atmosphere, plus hotel rooms, restaurants and pools on the resort. It’s a fun look, but you’re paying for that resort layer whether or not you use it, and depending on your booking, Margaritaville may charge a separate resort fee on top of the cottage rate.
Windsor Hills is more straightforward. You choose a privately owned condo, townhouse or house, and registered guests have access to the community amenities: the heated zero-entry lagoon pool and hot tub, Sir Windsor’s AquaVenture water park with its slides and splash zone, and a clubhouse with a games room, movie theater, fitness center and the Marketplace & Grill.
Space and private pools
Margaritaville cottages range widely in size, and some categories include private pools or spas. Windsor Hills offers 2- and 3-bedroom condos, 3-bedroom townhouses with private splash pools, and 4- to 6-bedroom homes and villas with private pools, each with a full kitchen and laundry. For most families, a townhouse with its own splash pool or a house with a private pool delivers more usable space than a cottage in a busy resort.
Atmosphere
Margaritaville is designed to feel like Margaritaville: themed and lively. Windsor Hills feels residential and family-focused, behind a gated entrance with 24-hour manned entry. Spend the morning at the water park, then come home, close the front door and have your own place in Florida.
Which offers better value?
Compare all-in prices, not headline rates: resort fees, booking charges, parking, bedroom count and kitchen setup. At Windsor Hills, most owners now include private pool heat at no charge, but confirm it before you book. Families who eat breakfast at home and spend most days inside Disney get little value from a heavier resort layer. Booking direct with a Windsor Hills owner can also help you avoid big-platform fees.
The verdict
Margaritaville is fun if you want a branded resort vibe. For families who want Disney proximity, real home-style space, a water park for rest days and a direct-booking experience, Windsor Hills is the better fit, and it leaves room for your family to make the trip its own. See Windsor Hills vacation rentals to browse options.
