About Windsor at Westside Resort
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Unleash your inner adventurer at Windsor at Westside, a dynamic gated resort in Kissimmee, 10 miles from Walt Disney World! This modern masterpiece boasts 4- to 9-bedroom homes with private pools, hot tubs, and high-tech game rooms packed with arcade machines and billiards, ideal for groups craving excitement. Set against Kissimmee’s vibrant energy, it’s a stone’s throw from ChampionsGate’s world-class golf courses and Old Lake Wilson’s fishing spots. Windsor at Westside blends sleek sophistication with non-stop fun, creating an electrifying vacation vibe that keeps everyone buzzing.
Amenities:
- Stunning 10,000-square-foot clubhouse anchoring a zero-entry pool, lazy river, and cascading waterfalls for a tropical escape.
- Festive tiki bar serving refreshing cocktails, an arcade bursting with games, and a snack bar for quick bites.
- Multi-sport facilities including soccer fields, sand volleyball, and basketball courts for action-packed days.
- Cutting-edge fitness center with Peloton bikes and free weights, plus shaded cabanas for poolside lounging.
- Manicured walking paths weaving through tropical gardens and tranquil ponds.
- Kids’ splash zone with interactive fountains and a dedicated toddler pool.
- Outdoor fire-pits and lounge areas for evening storytelling under the stars.
16 properties available
Welcome to Your Dream Vacation HomeStep into a beautifully designed vacation home where comfort, luxury, and imagination come together. From the moment you arrive, you’ll notice the open-concept layout, stylish furnishings, and thoughtfully designed spaces created for families and groups to relax, play, and make lasting memories.⸻⭐ First Floor High
Check yourself into this luxury family home and be greeted with bright, sun-filled living with soft comfortable furnishings and a spacious open plan design with room for everyone to spread out and have their own space. ⭐️FIRST FLOOR⭐️Relax on the lounge after a day spent at Disney and stream all your favorites on the big screen Smart TV – the perfe
Unlock 10% Off When You Stay a Week or More!Step into this bright, luxurious family villa with sun-filled living spaces, plush furnishings, and an open-concept layout perfect for group comfort.First FloorUnwind in the cozy lounge with a Smart TV—ideal for family movie nights after a day at Disney. The fully equipped kitchen has everything you need
Check yourself into this luxury family home and be greeted with bright, sun-filled living with soft comfortable furnishings and a spacious open plan design with room for everyone to spread out and have their own space. FIRST FLOORRelax on the lounge after a day spent at Disney and stream all your favorites on the big screen Smart TV – the perfect p
Check into this bright and spacious luxury family home, where comfort, style, and fun come together. Designed with open-plan living and soft, sunlit interiors, there’s plenty of space for everyone to spread out and feel right at home.FIRST FLOOR Unwind in the cozy lounge after a day at Disney, and enjoy your favorite shows on the oversized Smart TV
★ Fully equipped kitchen★ Washer and dryer★ Secure key-less entry to unit★ Located in the Windsor at Westside Resort★ All inclusive Club House nearby (you will have full access to everything there!)★ 11.6 miles to Disney (a 25 min drive), 19 miles to Universal Studios (32 min drive)★ Managed and maintained by a professional managing company with as
Your Private Resort-Style Oasis Near DisneyStep inside this light-filled, designer-furnished villa and feel an instant sense of calm. Walls of windows, plush seating, and a wide-open floor plan let everyone spread out yet stay connected—perfect for families who want both together time and personal space.Main Level – Relax, Dine, Gather • Great Room
Embark on an unforgettable journey at our lavish 5-bedroom family condo located in the exclusive Windsor at Westside Resort. Just a stone's throw from Disney World and Orlando's top attractions, our room combines relaxation and endless fun.Living Room: Relax in a cozy setting with comfortable sofas, a large smart TV, and elegant décor – perfect for
✨ Your Private Pool Getaway Near DisneyUnwind in this spacious 5-bedroom home in Windsor at Westside, featuring your own private pool & spa, a fun-filled game loft, and themed bedrooms the whole family will love.Just a short drive to Disney, this is the perfect base for your Orlando vacation.⸻🏡 The SpaceDesigned for comfort and connection, this ho
Check yourself into this luxury family home and be greeted with bright, sun-filled living with soft comfortable furnishings and a spacious open plan design with room for everyone to spread out and have their own space. ⭐️FIRST FLOOR⭐️Relax on the lounge after a day spent at Disney and stream all your favorites on the big screen Smart TV – the perfe
Welcome to your dream vacation at our magnificent 9-bedroom, 6.5-bathroom villa in Windsor at Westside Resort, Kissimmee, Florida. Perfect for Disney lovers, this luxurious retreat offers a blend of enchantment and comfort.🌟Luxurious Interior & Themed Rooms:🛏️ 9 beautifully appointed bedrooms (including themed rooms for an added touch of magic)🛁
Embark on an unforgettable journey at our lavish 5-bedroom family haven located in the exclusive Windsor at Westside Resort. Just a stone's throw from Disney World and Orlando's top attractions, our room combines luxury, relaxation, and endless fun.🏡 Inside the Home:Living Room: Relax in a cozy setting with comfortable sofas, a large smart TV, and
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