Westside Cay Homes with Restaurant Community Features

Welcome to Westside Cay, a hidden gem nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming subdivision offers a delightful blend of modern living and community spirit, making it an ideal place for families, retirees, and everyone in between.

Westside Cay is renowned for its thoughtfully designed homes that cater to a variety of lifestyles. Each residence showcases contemporary architecture, spacious layouts, and beautifully landscaped yards, providing the perfect backdrop for your new life in sunny Florida. With a range of options available, from cozy single-family homes to more expansive properties, you're sure to find the perfect fit for your needs.

One of the standout features of Westside Cay is its community-oriented atmosphere. Residents enjoy access to a variety of amenities, including a sparkling community pool, well-maintained parks, and walking trails that encourage outdoor recreation and social interaction. But that’s not all! The neighborhood boasts a charming restaurant community, making it easy to indulge in delicious meals without ever having to leave home. Whether you're in the mood for a casual bite or a fine dining experience, you’ll find a variety of culinary delights just around the corner.

Living in Westside Cay means embracing a lifestyle of convenience and comfort, with easy access to major highways, shopping centers, and entertainment options. Plus, the enchanting attractions of Kissimmee and the magical world of Walt Disney are just a short drive away.

Discover the warmth and charm of Westside Cay – your dream home awaits!

Newest Westside Cay Homes with Restaurant Community Features

$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, 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.

2591 Santorini Divide, 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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