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Windsor at Westside

Nestled in Kissimmee, this community blends high-return potential with vacationer appeal.

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Welcome to Windsor at Westside

Premier Short-Term Rental Investment & Luxury Vacation Living Near Disney
 
Nestled in Kissimmee, Windsor at Westside is a gated, resort-style community offering unmatched proximity to Walt Disney World (6–8 miles) and Universal Studios (15–20 miles), making it a prime choice for short-term rental investors and vacation home buyers. With its 10,000 sq. ft. clubhouse, cutting-edge amenities, and diverse property portfolio, this community blends high-return potential with vacationer appeal.
 

Resort-Style Amenities for Guests & Owners

Windsor at Westside elevates resort living with exclusive features:
 
  • Zero-entry pool complex: Lazy river, dual water slides, heated spa, and kids’ splash zone.

  • Tu Casa Tiki Bar & Lounge: Poolside dining with favorites like Crispy Chicken Bacon Wraps and tropical cocktails.

  • Fitness & Recreation: State-of-the-art gym, sand volleyball, tennis/basketball courts, and a 24/7 arcade.

  • Family-Friendly Perks: Kids’ activity center with ice cream robots, movie theater, and lakeside fire pit.

Diverse Property Options for Every Investor

From cozy townhomes to sprawling estates, Windsor at Westside caters to all:
 
  • Property Type: Townhomes, Single-Family Homes

  • Bedrooms: 4–5, 5–9+

  • Key Features: Private splash pools, modern designs, walkability. Themed bedrooms (Star Wars, Mickey), private screened pools, game rooms, in-home theaters.
All properties include full kitchens, laundry, free Wi-Fi, and optional pool heating.
 

Prime Location & Local Attractions

  • Disney World: 10-minute drive via Highway 429.

  • Universal/SeaWorld: 15–25 minutes by car.

  • Local Conveniences: Publix Supermarket (3 miles), Posner Park shopping, and diverse dining on US 192.

  • Beach Access: Cocoa Beach and Clearwater within 90 minutes.

Investor Advantages

  • High Occupancy: Ranked among Orlando’s top rental communities since 2015.

  • Zero Resort Fees: Owners retain 100% rental income with no hidden costs.

  • Flexible Management: Choose third-party or self-management with 24/7 security and maintenance.

  • Proven Demand: Proximity to Disney ensures year-round bookings.

Unique Features for Competitive Edge

  • Themed Bedrooms & Game Rooms: Attract families with immersive Disney, Star Wars, or superhero decor.

  • Private Pools & Spas: Standard in all homes, with optional heating for cooler months.

  • Event-Ready Spaces: Cabana rentals, sports facilities, and lakeside pier for group gatherings.

Secure Your Slice of Orlando’s Magic

Windsor at Westside merges investor-friendly infrastructure with vacationer luxuries. Explore 4–9 bedroom homes, townhomes, and condos—each a gateway to Orlando’s top attractions.
Aerial view of a community pool with waterslides, a lazy river, clubhouse, tennis courts, and lakefront dock. Two-story cream house with brown trim, a double garage, paved driveway, and palm tree. Aerial view of a community clubhouse and pool surrounded by palm trees and homes. Community lobby with a high coffered ceiling, chandeliers, and circular white seating. Outdoor court with basketball hoops, a central net, and palm trees beyond the fence. Community pool with a colorful water-play structure, palm trees, and rows of blue lounge chairs. Game room with an air hockey table, racing arcade machines, and upright arcade cabinets. Tu Casa Bar & Lounge patio with wicker seating and a square fire table. Community pool with turquoise loungers, a blue cabana, and colorful floats. Aerial view of homes around a lake, with a clubhouse and swimming pool. Outdoor basketball court with a central hoop, colorful court markings, and palm trees beyond the fence. Two colorful frozen drinks with citrus garnishes sit beside a resort-style pool. Community playground with a shaded climbing structure and slide. Windsor at Westside splash pad with a water-play structure spraying into the pool beside the clubhouse.

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