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Windsor Hills Resort

Windsor Hills Resort Orlando is a secure gated resort-style community ideally located in Western Kissimmee just a short drive from Disney World Resort, offering guests a fabulous range of on-site leisure amenities.

This family-oriented community set in lush tropical landscaped grounds features a large Clubhouse with leisure amenities including a resort-style swimming complex with a large pool, waterslides and extensive sun decking which will be sure to please adults and children alike, inviting guests to an ideal spot to relax and unwind after a day at one of the Orlando Theme Park Attractions 

Choose your rental from 2 and 3 Bed Condominium Apartments, 3 Bed Townhouses with Splash Pool and 4, 5 and 6 Bed detached Homes with Swimming Pool

To find out more visit our About Windsor Hills page and there is a Windsor Hills video for you to view further down the home page.

If you would like to view a list of our featured Orlando communities that offer resort style leisure amenities throughout Kissimmee, Clermont, Davenport and International Drive please visit our Orlando Villa Rentals website.  If you need some assistant go to out Contact Us page.

Windsor Hills Resort Video

Why to Stay at Windsor Hills Resort

Windsor Hills Resort Orlando | Florida Vacation Home Rentals
Premier Resort-Style Club Experience – The massive staffed Clubhouse is the vibrant heart of Windsor Hills Resort, featuring a state-of-the-art fitness center/gym, games room/arcade (with billiards, ping-pong, video games), 800+ movie theater, sundry shop/marketplace (with snacks, groceries, grill for pizza/burgers), lounge areas, business center, and seamless integration with the expansive outdoor water park and amenities for a complete, family-focused resort hub onsite
 
Prime Orlando Location – Gated community in Kissimmee with easy access to major roads, just 1.5-2 miles (5-10 min drive) to Walt Disney World main entrances, 25-35 mins to Universal Orlando & SeaWorld, and about 30-35 mins from Orlando International Airport – one of the closest resorts to the parks for minimal travel time
 
Variety of Luxury Rentals – Spacious 3- to 9-bedroom detached villas, homes, townhomes, and condos sleeping 8-20+ guests, with full kitchens, open living areas, multiple ensuites, game rooms/movie theaters (in many), themed bedrooms (in select), and high-end finishes—perfect for families and groups of all sizes seeking home-like comfort
 
Private Pools in Most Homes – Many properties feature their own screened private pool (often heated with spa/hot tub options and covered lanai areas) for ultimate private relaxation and Florida-style outdoor enjoyment, with townhomes/condos offering easy access to the resort’s shared pools
 
Expanded Resort Pool & Water Park Features – FREE access to the heated zero-entry lagoon pool (140,000 gallons, year-round), Sir Windsor’s AquaVenture Water Park (with dueling large waterslides, smaller slides, giant interactive kids’ splash pad), large hot tub (10-person), sun deck with loungers/cabanas, and poolside marketplace/grill for food/drinks – perfect for family splashing and thrills
 
Fun Onsite Activities – Fitness center, arcade/games room, movie theater, playgrounds (multiple, including castle-themed), sand volleyball, basketball/tennis courts, putting green, and more complimentary options for active family entertainment and downtime
 
Ultimate Convenience Onsite – Secure 24/7 gated resort with lush landscaping, marketplace for essentials/takeaway, poolside service, high-speed Wi-Fi, wristband-required amenities (free from clubhouse), and nearby shops/dining—spend more time enjoying your vacation and less time traveling
 
Superior Space & Value – Full kitchens, open-plan living/dining areas, laundry facilities, high-end furnishings, serene surroundings, and private pool perks (in most rentals) – far more room, privacy, and better value than any hotel for multi-generational family vacations