KISSIMMEE, FLORIDA
Discover what makes Windsor Hills one of Central Florida's most sought-after locations for vacation rental investment.
Windsor Hills Resort's unbeatable location near Orlando's world-famous theme parks is the primary driver of strong vacation rental demand year-round. Here's what's nearby:
The world's most visited theme park resort featuring Magic Kingdom, EPCOT, Hollywood Studios, and Animal Kingdom. Windsor Hills is the closest vacation home community to Disney's main entrance.
Closest resort communityHome to Universal Studios, Islands of Adventure, and the Wizarding World of Harry Potter. The new Epic Universe park opens in 2025, adding even more value to nearby properties.
Epic Universe opening 2025Marine life park featuring world-class roller coasters, animal encounters, and live shows. Includes the thrilling Mako, Kraken, and Manta coasters.
Top-rated coastersPerfect for families with children ages 2–12. Features over 50 rides, shows, and attractions, plus a water park and botanical gardens in Winter Haven.
Great for young familiesFrom quick bites along US-192 to upscale restaurants at nearby resorts, there's no shortage of dining options near Windsor Hills.
The Venetian Chop House
Upscale steakhouse at Caribe Royale, 5 min drive
Bull & Bear
Award-winning steakhouse at Waldorf Astoria, 10 min
Giordano's Pizza
Famous Chicago deep-dish, US-192, 3 min drive
Miller's Ale House
Casual American dining, US-192, 4 min drive
Bob Evans
Family-style breakfast & comfort food, 3 min
Chick-fil-A
US-192, 3 min drive
Wawa
Gas station & fresh food, next to community entrance
Publix Deli
Fresh subs & meals at the nearby Publix supermarket
Over 160 designer and name-brand stores including Nike, Coach, Michael Kors, and more. One of the most visited outlets in the US.
Open-air shopping center with Target, Best Buy, Ross, Marshalls, and dozens of restaurants and entertainment options.
Full grocery and general merchandise store just minutes from Windsor Hills — perfect for stocking up on vacation essentials.
Florida's favorite grocery chain, located on US-192 near the Windsor Hills entrance. Deli, bakery, and pharmacy available.
While most Windsor Hills owners use their properties as vacation rentals, the surrounding Osceola County area offers quality school options for full-time residents.
Elementary
Middle
High School
K–8 (A-rated)
Windsor Hills is located off US-192 (Irlo Bronson Memorial Highway), providing easy access to I-4 and all major Orlando attractions. Most guests rent a car, though ride-sharing services are readily available.
Orlando International Airport (MCO) is approximately 25 miles east, a 30–40 minute drive. Orlando Sanford International Airport is about 50 miles north.
Cocoa Beach and the Atlantic coast are about 70 miles east (roughly 1 hour 15 minutes). Clearwater Beach on the Gulf Coast is about 100 miles west (approximately 1 hour 45 minutes).
Old Town Kissimmee entertainment district (5 min), Gatorland (15 min), ICON Park Orlando (15 min), and the Kennedy Space Center (1 hour) are all popular day-trip options.
Explore available properties or download our free income report to see what you could earn.
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Contact Holiday Realty LLC today for a free consultation. We'll help you buy or sell your Windsor Hills Resort property.