Windward Cay

Kissimmee’s Hidden Gem: Windward Cay Holiday Villa Resort

Windward Cay is a medium-sized, serene community, home to approximately 150 detached villas. Each villa is a testament to the beauty and tranquillity of Florida’s natural landscape. Tall, majestic trees flank these homes, providing a canopy of shade and a sense of privacy. The community is further enhanced by the presence of conservation land and a picturesque small lake, offering residents and guests a peaceful retreat from the bustling attractions nearby. Nestled in the heart of Kissimmee, Orlando, the Windward Cay Holiday Villa Resort is a hidden gem for UK holidaymakers seeking the quintessential Florida experience. A mere 15-20 minute drive from the magical realm of Walt Disney World and a convenient 25-30 minute journey to the thrilling Universal Orlando theme parks, this resort is the perfect base for families and groups eager to explore the wonders of Florida.

Windward Cay Villas: A Blend of Luxury and Comfort

Our selection of splendid 3 and 4-bedroom detached villas, all with its own private swimming pool, promise a stay that is both luxurious and homely.

As you step into one of our Windward Cay villas, you’re immediately welcomed by a spacious, contemporary setting that radiates both elegance and warmth. The harmonious blend of modern amenities and refined decor creates an ambiance of sophistication, making every moment spent inside memorable.

The living area, a central hub of the villa, is accentuated with plush, comfortable sofas. This space, bathed in natural light, provides an idyllic setting for families and friends to come together. For those who find joy in cooking, the modern kitchens are nothing short of a culinary haven. Decked out with gleaming stainless steel appliances and chic countertops, they cater to every culinary need, be it whipping up a quick snack or crafting a lavish feast. Morning risers can enjoy a hearty breakfast at the stylish breakfast bar, while dinner can be a grand affair at the expansive dining table. And for those moments when you crave an alfresco experience, dining by the pool under the starlit sky, accompanied by the gentle chirping of crickets and the clink of wine glasses, is simply magical.

But the allure of our villas doesn’t end indoors. The private pool area is a sanctuary of relaxation. Many of our villas boast either serene lake views or overlook the untouched beauty of conservation areas, offering guests a tranquil backdrop as they take a refreshing dip or lounge by the poolside.

When the day draws to a close, our bedrooms stand ready to envelop you in a cocoon of comfort. The master suite, a realm of luxury, is furnished with a sumptuous king-size bed, ensuring a night of undisturbed rest. Complementing this is a lavish ensuite, complete with double sinks for added convenience, and a spacious walk-in wardrobe to house all your holiday essentials.

Easy Grocery Runs at Windward Cay

Staying at Windward Cay ensures that keeping your kitchen filled with food, beverages, and snacks is a breeze. The villa’s prime location offers easy access to a variety of supermarkets, making it simple and stress free to stock up on all your  essentials. Right around the corner, just a short 5 minute drive, is the expansive Walmart store, boasting a vast array of groceries to cater to every palate. A few hundred yards further along US192 are Aldi and Publix supermarkets, further broadening your shopping options and ensuring your kitchen is always well-supplied.

Old Town Kissimmee: The Perfect Post-Park Destination

After a thrilling day meeting beloved characters at Walt Disney World and Universal Orlando theme parks, the allure of the Kissimmee area continues with Old Town Kissimmee, located just a short 10-minute drive west from Windward Cay. This family-friendly entertainment district seamlessly blends classic American fun with modern entertainment, transporting visitors to a nostalgic era while offering contemporary attractions.

As you wander through the charming streets of Old Town, you’re greeted by a diverse culinary scene, from fast and casual eateries to full-service restaurants and bars, ensuring every palate is catered to. Beyond dining, the district boasts an array of attractions that promise to entertain and delight. Whether you choose to take a nostalgic ride on the classic Carousel, soar high on the Ferris Wheel for breathtaking views, or seek adrenaline rushes on the Hurricane roller coaster, there’s something for everyone. The Xtreme Ninja Challenge offers a test of strength and endurance, while families can bond over games at the Happy Days Family Fun Center or test their aim at Rootin & Tootin’s Shootin’ Alley. For those who enjoy a touch of the macabre, Mortem Manor provides a spine-chilling experience.

But the charm of Old Town doesn’t end with its attractions. Every Saturday, the streets come alive with the Old Town Classic Car Show, a local tradition for over 30 years. Car enthusiasts and visitors alike gather to admire a stunning collection of classic vehicles, making it a highlight in Central Florida’s weekly events.

From Dining to Cinema: The Loop Experience Awaits

The Loop in Kissimmee is not just a shopping hub; it’s a vibrant experience waiting to be explored. Situated a mere 15-minute drive from Windward Cay, this multifaceted plaza is the perfect spot to unwind after an exhilarating day at the theme parks. Food enthusiasts will be spoilt for choice with an array of dining options. Dive into the rich flavors at Chili’s, where the menu boasts favorites like Chicken Fajitas served with a side of rice, beans, tortillas, guacamole, salsa, and sour cream. For pasta lovers, the Ultimate Cajun Pasta with grilled chicken, shrimp, and Alfredo sauce is a must-try. If you’re in the mood for pizza, Pienezza Pizza promises a delightful treat. For those with a sweet tooth, Ben and Jerry’s Ice Cream parlour is the place to be. And for movie buffs, the Regal Movie theatre showcases the latest blockbusters, ensuring entertainment is always at its peak. Whether you’re in the mood for a hearty meal, a sweet treat, or a cinematic experience, The Loop has got you covered.

Tee Off Moments from Windward Cay

For golf enthusiasts staying at Windward Cay, the location couldn’t be more ideal. The resort’s proximity to some of the region’s most renowned golf courses ensures that golfers have an array of options to indulge in their passion.

Just a short 10-minute drive away is the Falcon’s Fire Golf Club, a course that stands out not just in Orlando but is recognized both regionally and nationally. Designed by the esteemed Rees Jones, this championship golf course offers an immaculate playing field complemented by the highest level of service and amenities. The course stretches over 7,000 yards from the back tees, providing golfers with four sets of tees to choose from, making it both challenging for seasoned players and enjoyable for those looking for a relaxing round. Beyond the course, the Falcon’s Fire Golf Club boasts the Falcon’s Nest Restaurant for exquisite dining and an award-winning golf shop equipped with the latest technology and apparel.

A mere 15 minutes away, golfers can also explore the stunning Celebration Golf Course, another gem in the region’s golfing crown. This meticulously designed course offers a blend of challenging play and scenic beauty, making it a must-visit for both novice and seasoned golfers. From the moment you step onto the greens, you’ll be captivated by the course’s intricate design and impeccable maintenance. Every hole offers a unique challenge, ensuring that players are engaged and tested throughout their round. But it’s not just about the play; the course is set against a backdrop of Florida’s stunning natural beauty, making every shot a picturesque moment.

Beyond the course, Celebration Golf Club provides a holistic golfing experience. Their state-of-the-art Golf Academy is helmed by experienced instructors who are committed to elevating your game. Whether you’re looking to refine your swing or master the art of the putt, the academy offers tailored lessons that cater to all skill levels.

Unrivalled Location: Windward Cay’s Access to Orlando’s Treasures

Windward Cay villas truly offer the best of both worlds. Nestled in a serene environment, they provide a tranquil retreat after a day of adventure, yet their prime location ensures that the vibrant heart of Orlando is always within reach. Whether you’re looking to experience the magic of the major theme parks, indulge in some retail therapy at local shopping hubs, enjoy an evening of entertainment, or tee off at some of the region’s top golf courses, Windward Cay is your perfect base. Don’t miss out on the ideal blend of relaxation and excitement. Book your stay at Windward Cay villas today and embark on an unforgettable Orlando adventure!