Westside Cay Homes with Sidewalks Community Features

Welcome to Westside Cay, a charming subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This delightful community is perfect for those seeking a serene yet connected lifestyle, offering the best of both suburban tranquility and urban convenience.

Westside Cay is designed with family-friendly living in mind, featuring beautiful homes with sidewalks that encourage leisurely strolls and friendly neighborly interactions. Imagine evening walks with your loved ones, where children can safely ride their bikes and play outside, creating memories that last a lifetime. The well-maintained sidewalks weave through the community, enhancing the sense of togetherness and promoting an active lifestyle.

The homes in Westside Cay are thoughtfully designed to cater to diverse tastes and preferences, showcasing modern architecture and spacious layouts that are perfect for entertaining or simply enjoying a quiet evening at home. With a variety of floor plans available, there’s something for everyone, whether you're a first-time homebuyer, a growing family, or looking to downsize.

In addition to its charming homes, Westside Cay boasts a prime location just minutes away from local attractions, shopping centers, and dining options that Kissimmee is known for. Enjoy easy access to the magical world of theme parks, beautiful natural preserves, and vibrant community events.

Experience the warmth and charm of Westside Cay, where community spirit thrives, and every day feels like a getaway. Discover your dream home in this picturesque neighborhood today!

Newest Westside Cay Homes with Sidewalks Community Features

$663,800

5 Beds ⋅ 5 Baths ⋅ Westside Cay SubDv. ⋅ 34747 Zip Code

Fully upgraded from floor to ceiling, this luxury townhome blends contemporary elegance with high-end functionality — designed specifically for short-term rental success. Located in the exclusive Doppio Westside community in Kissimmee, just 15 minutes from Walt Disney World, this 5-bedroom, 4.5-bath home features an open-concept layout with spacious integrated living, dining, and kitchen areas that flow seamlessly to your own private heated pool. The kitchen is a showstopper with two oversized islands, Level 5 quartz countertops, designer backsplash, slatted wood detail, and Whirlpool stainless steel appliances. All cabinetry throughout the home includes soft-close features and matte hardware for a sleek, modern finish. Each of the five bedrooms is designed with comfort and rental flexibility in mind — including four full en-suites and one located on the first floor. The bathrooms are finished with high-end porcelain tile, glass shower enclosures, built-in niches, and vessel sinks in select locations. Luxury vinyl plank flooring runs throughout the entire home — no carpet anywhere — and 5.5" square baseboards give a clean, elevated look. Additional features include PVC windows, a smart front door lock, a lockable owner’s closet, a hybrid water heater, thermostat, and 2 Car Parking Spot. Construction is full concrete block, including second floor, with an insulated "sandwich" roof system and rubber membrane roofing designed for durability and energy efficiency. Located within a gated community, Doppio Westside offers resort-style amenities such as a lagoon-style pool, full-service restaurant, clubhouse with front desk concierge, fitness center, playground, convention center, and EV charging stations — all exclusively zoned for short-term rental with no public school restrictions. Don't miss this opportunity to invest in one of Central Florida’s most unique STR communities — fully upgraded as standard, and built with both guest experience and investor return in mind.

2603 Santorini Drive, Kissimmee

$595,000

5 Beds ⋅ 5 Baths ⋅ Westside Cay SubDv. ⋅ 34747 Zip Code

Fully upgraded from floor to ceiling, this luxury townhome blends contemporary elegance with high-end functionality — designed specifically for short-term rental success. Located in the exclusive Doppio Westside community in Kissimmee, just 15 minutes from Walt Disney World, this 5-bedroom, 4.5-bath home features an open-concept layout with spacious integrated living, dining, and kitchen areas that flow seamlessly to your own private heated pool. The kitchen is a showstopper with two oversized islands, Level 5 quartz countertops, designer backsplash, slatted wood detail, and Whirlpool stainless steel appliances. All cabinetry throughout the home includes soft-close features and matte hardware for a sleek, modern finish. Each of the five bedrooms is designed with comfort and rental flexibility in mind — including four full en-suites and one located on the first floor. The bathrooms are finished with high-end porcelain tile, glass shower enclosures, built-in niches, and vessel sinks in select locations. Luxury vinyl plank flooring runs throughout the entire home — no carpet anywhere — and 5.5" square baseboards give a clean, elevated look. Additional features include PVC windows, a smart front door lock, a lockable owner’s closet, a hybrid water heater, thermostat, and 2 Car Parking Spot. Construction is full concrete block, including second floor, with an insulated "sandwich" roof system and rubber membrane roofing designed for durability and energy efficiency. Located within a gated community, offers resort-style amenities such as a lagoon-style pool, full-service restaurant, clubhouse with front desk concierge, fitness center, playground, convention center, and EV charging stations — all exclusively zoned for short-term rental with no public school restrictions. Don't miss this opportunity to invest in one of Central Florida’s most unique STR communities — fully upgraded as standard, and built with both guest experience and investor return in mind.

9058 Hayman Lane, Kissimmee

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