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Windsor at Westside Resort

Windsor at Westside Resort is a premier style rental community ideally located in West Kissimmee, south of US Highway 192 and situated within a short drive of Disney World Resort Orlando.

This exciting community features an extensive range of on-site leisure amenities including Clubhouse, resort-style swimming pool, lazy river, waterslides and much more, surrounded with extensive sun decking overlooking the scenic lake, offering guests an ideal spot to relax and unwind after a day at the Orlando Theme Parks 

Your choice of Windsor at Westside Resort rental properties are 4 & 5 Bed 2 story Townhouses with splash pool and 5, 6, 7 8 & 9 Bed Detached Homes with private swimming pool.

To find out more visit our About Windsor at Westside 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.

Windsor at Westside Resort Video

Why to Stay at Windsor at Westside

Windsor at Westside | Disney Area Luxury Vacation Homes | Realty in Orlando
Premier Resort-Style Club Experience – The extraordinary 10,000 sq ft Mediterranean-themed Clubhouse is the vibrant heart of Windsor at Westside, featuring a state-of-the-art fitness center, video arcade/game room, sundry shop, lounge areas with fireplace, business/computer access, 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 West Kissimmee with easy access to toll road 429, Highway 192, and I-4, just 7-10 min drive (about 7-8 miles) to Walt Disney World main entrances, 25-35 mins to Universal Orlando & SeaWorld, and roughly 30 mins from Orlando International Airport – ideal for quick theme park trips and nearby dining/shopping
 
Variety of Luxury Rentals – Spacious 4- to 9-bedroom detached villas, single-family homes, and townhomes sleeping 8-20+ guests, with full kitchens, open living areas, multiple ensuites, game rooms/movie theaters (in many), and high-end finishes—perfect for large families and groups seeking home-like comfort
 
Private Pools in Every Home – Each property features its own screened private pool (often heated with optional spa/hot tub and covered lanai areas) for ultimate private relaxation and Florida-style outdoor enjoyment
 
Expanded Resort Pool & Water Park Features – FREE access to the stunning zero-entry resort-style lagoon pool (heated with twisting waterslide, lazy river, kids’ water playground/splash pad, sun deck, loungers, cabanas), plus Tu Casa Tiki bar & grill for poolside food/drinks and a fireplace lounge for family splashing and casual vibes
 
Fun Onsite Activities – Fitness center, video arcade, sand volleyball courts, children’s playground elements (in water play area), and more complimentary options for active family entertainment and downtime
 
Ultimate Convenience Onsite – Secure gated resort with lush landscaping, lake & pier views, multiple dining/snack options (Tiki bar, sundry shop), poolside service, high-speed Wi-Fi, 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 – far more room, privacy, and better value than any hotel for multi-generational family vacations