Westside Cay Homes with Pool

Welcome to Westside Cay, a charming subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This idyllic community perfectly blends modern living with the laid-back lifestyle that Florida is known for. With its prime location, residents enjoy easy access to a myriad of attractions, including world-renowned theme parks, shopping centers, and a variety of dining options that cater to every palate.

Westside Cay is particularly appealing for those who cherish outdoor living, as many of the homes in this community come equipped with private pools. Imagine stepping out into your backyard oasis, where you can bask in the Florida sun, host unforgettable pool parties, or unwind with a refreshing swim after a long day. These homes are designed with family-friendly features, ensuring that every member of your household can enjoy the joys of poolside living.

The subdivision offers a range of beautifully designed homes, each showcasing modern architecture and spacious interiors that are perfect for both entertaining and relaxation. With well-maintained landscaping and a welcoming atmosphere, Westside Cay is not just a place to live; it’s a place to thrive.

Whether you’re a first-time homebuyer, looking to invest in a vacation rental, or seeking a peaceful retreat, Westside Cay offers something for everyone. Experience the allure of Florida living in this delightful community, where your dream home with a pool awaits! Come and discover why Westside Cay is the perfect place to call home.

Newest Westside Cay Homes with Pool

$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

$580,000

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

Experience luxury, style, and exceptional investment potential in this fully upgraded 5-bedroom, 4.5-bathroom townhome located in the exclusive Doppio Westside Resort, one of Central Florida’s newest premier short-term rental communities. Just 15 minutes from Walt Disney World, this contemporary residence was thoughtfully designed to maximize both guest experience and owner returns. From the moment you enter, you’ll appreciate the spacious open-concept design featuring expansive living and dining areas that seamlessly connect to the private heated pool, creating the perfect indoor-outdoor entertainment space. The chef-inspired kitchen is a true centerpiece, showcasing two oversized islands, Level 5 quartz countertops, a designer backsplash, elegant slatted wood accents, Whirlpool stainless steel appliances, and premium soft-close cabinetry with sleek matte hardware throughout. Designed with flexibility and comfort in mind, the home offers five spacious bedrooms, including four luxurious en-suite bedrooms and a convenient first-floor bedroom, making it ideal for large families and vacation groups. Every bathroom features designer porcelain tile, frameless glass shower enclosures, built-in niches, and stylish vessel sinks in select bathrooms. Luxury Vinyl Plank flooring extends throughout the entire home with absolutely no carpet, while oversized 5.5-inch square baseboards add a luxury custom finish. Additional premium features include PVC impact-resistant windows, smart front door lock, owner’s lockable storage closet, hybrid water heater, smart thermostat, and two dedicated parking spaces. Built for long-term durability and efficiency, the home features full concrete block construction on both the first and second floors, an insulated sandwich roof system, and a rubber membrane roofing system designed for superior performance and energy efficiency. Located within a gated resort community, Doppio Westside offers an impressive collection of resort-style amenities including a spectacular lagoon-style swimming pool, full-service restaurant, elegant clubhouse with concierge services, state-of-the-art fitness center, playground, convention and event center, and electric vehicle charging stations. Best of all, the community is fully approved and exclusively zoned for short-term rentals, offering investors outstanding flexibility and rental income potential. Whether you’re searching for a high-performing vacation rental, a second home, or a smart addition to your investment portfolio, this exceptional property delivers luxury, quality construction, and an unbeatable location in the heart of Central Florida

9084 Boracay Court, Kissimmee

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