Westside Cay Homes with Pool Community Features

Welcome to Westside Cay, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida. Known for its picturesque landscapes and charming community spirit, Westside Cay offers a perfect blend of comfort and convenience for families and individuals alike. This thriving neighborhood is ideally located in Osceola County, providing easy access to the best attractions that Central Florida has to offer, including the magical realms of Walt Disney World and the thrilling adventures of Universal Studios.

One of the standout features of Westside Cay is its stunning homes, many of which come complete with private pools. Imagine stepping into your backyard oasis, where you can unwind under the Florida sun or host delightful gatherings with family and friends. The community’s pool homes are designed with luxury and relaxation in mind, ensuring you can enjoy the ultimate Florida lifestyle right at your doorstep.

Westside Cay is more than just a collection of homes; it’s a community that fosters connection and camaraderie. Residents enjoy access to beautifully landscaped parks, walking trails, and recreational areas, making it easy to stay active and engaged. With a friendly atmosphere and a strong sense of belonging, Westside Cay is the perfect place to create lasting memories.

Whether you’re a first-time homebuyer or looking to invest in a vacation property, Westside Cay offers a variety of options that cater to your needs. Come explore this enchanting community and discover why so many are choosing to call Westside Cay home. Your dream home awaits!

Newest Westside Cay Homes with Pool 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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