Windsor Hills Resort remains one of Kissimmee’s most established “Gold Standard” gated vacation communities in 2026. Located less than two miles from Walt Disney World, this professionally managed resort blends true proximity to the parks with a fully built-out amenity infrastructure designed for high-volume family travel. Its strength lies not just in amenities, but in operational efficiency. With updated security protocols, structured access systems, and refreshed on-site facilities, Windsor Hills delivers a seamless arrival and stay experience for guests who are properly prepared. Amenities:

Community & Setting

• 24/7 guard-gated resort with controlled entry
• Under 2 miles to Walt Disney World property
• Fastest Disney access via Entry Point Blvd → Sherberth Road (Animal Kingdom corridor)
• Landscaped grounds with sidewalks and walking paths
• Designed exclusively for short-term vacation rentals

Pools & Water Features

• Free access to the resort water park (wristbands required; obtained at clubhouse with rental agreement)
• Large zero-entry lagoon pool
• Dual water slides (refreshed January–February 2026; fully operational)
• Interactive children’s splash zone
• Spacious sun deck with shaded seating
• Two oversized heated hot tubs

• Wristbands are mandatory for entry
• Guests must present rental agreement at clubhouse to receive bands
• Security strictly enforces access to prevent overcrowding

• Many villas include private screened pools
• Optional pool heat available through property management
• Covered lanais and outdoor dining areas

Clubhouse & Indoor Amenities

• Expansive resort clubhouse with guest lounge areas
• Cyber Café with printing access
• Fitness center with cardio and strength equipment
• Arcade and games room
• Free high-speed Wi-Fi throughout clubhouse and pool areas

• High-definition projection system
• Library of 800+ movie titles
• Guests may request specific films when theater is not reserved
• Scheduled daily showings

• Expanded hot food menu (pizza, burgers, sandwiches)
• Fresh coffee and breakfast items
• Vacation essentials and convenience goods
• Ideal for quick meals without leaving the resort

Sports & Recreation

• Lighted tennis courts
• Basketball court
• Sand volleyball
• 9-hole mini golf course
• Children’s playground
• Walking and jogging paths

• First-come, first-served (no reservations permitted)
• Arrive early for prime play times

• Tennis racquets, basketballs, and putters available
• Small refundable deposit required at Welcome Center

Accommodations

• 3 to 8+ bedroom villas and townhomes
• Fully equipped kitchens
• In-unit washer and dryer
• Open-concept living areas
• Private screened pools in many homes
• Driveways (no garages typically available for guest parking)

Security & Parking (Critical 2026 Operational Rules)

• All guests must be pre-registered by the property owner or manager
• Guests not on the guard’s list will be denied entry — even with booking confirmation

• Maximum of 3 vehicles per villa
• Strictly enforced

• Street parking prohibited
• Vehicles blocking sidewalks or parked on grass are towed immediately
• Policy ensures emergency vehicle access

Transportation & Access Tips

• Under 10 minutes to Animal Kingdom area via Sherberth Road shortcut
• Rental car strongly recommended
• Uber/Lyft drivers must be authorized through guard gate or resort app
• If rideshare is not pre-authorized, drivers will be turned away