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Windsor Hills Resort

Family-friendly luxury just 2 miles from Walt Disney World. A gated resort with a lagoon-style pool, waterslide, clubhouse, and spacious villas that families come back to year after year.

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One of the Closest Resorts to Disney

Windsor Hills is one of the most established and trusted vacation home communities in Central Florida, sitting just 2 miles from Walt Disney World's main gates. Known for its unbeatable location, family-friendly atmosphere, and gated security, this resort is a favorite for travelers who want convenience and comfort in equal measure.

Whether you're traveling with toddlers or bringing the whole extended family, Windsor Hills offers a relaxed, upscale environment with all the amenities you need. Beautifully maintained grounds, a stunning lagoon-style pool, and homes ranging from cozy 2-bedroom condos to spacious 6-bedroom villas mean there's a perfect fit for every group. Located off Old Lake Wilson Road near US-192 in the heart of Kissimmee's vacation corridor, it offers quick access to I-4 and all of Orlando's top attractions.

One of the Closest Resorts to Disney

Why Families Choose Windsor Hills

One of Central Florida's most trusted vacation resorts

  • Just 2 miles from Disney's main gates

  • Lagoon pool, waterslide & splash pad

  • Gated community with 24/7 security

  • 2 to 6 bedroom villas and condos

The Clubhouse & Pool

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The Windsor Hills clubhouse is the heart of the community, featuring a lagoon-style pool with waterslide, splash pad, hot tub, fitness center, movie theater, game room, and sports courts. Guests also enjoy an on-site market and grill, with full access included and no resort fees.

Dining & Shopping on Your Doorstep

Windsor Hills puts everyday essentials within arm's reach. Walmart Supercenter is less than 2 minutes away, with Publix and Target close behind. When you'd rather eat out, you're surrounded by options: Chick-fil-A, Olive Garden, LongHorn Steakhouse, Applebee's, and dozens more sit along US-192.

For something different, visit Island Grove Wine Company at Formosa Gardens for a unique local experience. You can also arrange grocery delivery to your villa before you arrive, or book a personal chef through our concierge services for a special evening in.

On-Site Amenities

Everything Your Family Needs

Water & Fun

Resort-level recreation for every age group

Lagoon-style pool with zero-entry access

Large waterslide and splash pad for kids

Hot tub and sun deck with loungers

Market & grill for snacks and essentials

Sports & Entertainment

Stay active and entertained between park days

Clubhouse movie theater and game room

Tennis, basketball & volleyball courts

Putting green and playground

Full fitness center with cardio and weights

Vacation Homes at Windsor Hills

From cozy condos for couples to spacious 6-bedroom villas for large families, every home is designed for comfort and convenience. Many feature themed kids' rooms, game areas, and poolside BBQs.
Vacation Homes at Windsor Hills

Private Pools & Screened Patios

Most villas include their own private screened pool and patio, giving your family a place to cool off and relax in complete privacy — just steps from the resort pool if you want the social scene.

Game Rooms & Themed Bedrooms

Kids love the themed bedrooms and dedicated game rooms with pool tables and arcades. These spaces keep everyone entertained between park visits and pool sessions.

Fully Equipped for Your Stay

Every home comes with a fully equipped kitchen, washer and dryer, smart TVs, free WiFi, towels, linens, starter toiletries, and driveway parking. Everything you need from day one.
Vacation Homes at Windsor Hills

Private Pools & Screened Patios

Most villas include their own private screened pool and patio, giving your family a place to cool off and relax in complete privacy — just steps from the resort pool if you want the social scene.

Game Rooms & Themed Bedrooms

Kids love the themed bedrooms and dedicated game rooms with pool tables and arcades. These spaces keep everyone entertained between park visits and pool sessions.

Fully Equipped for Your Stay

Every home comes with a fully equipped kitchen, washer and dryer, smart TVs, free WiFi, towels, linens, starter toiletries, and driveway parking. Everything you need from day one.

Know About Our Resorts

Fourteen premier communities across Orlando, each with pools, amenities, and easy access to the parks. Find the one that fits your family.

Encore Resort

Reunion Resort

Emerald Island Resort

Storey Lake Resort

Solterra Resort

Championsgate Resort

Ready to Book

Stay Close to the Magic

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