Rolling Oaks Ph 5 Homes with Restaurant Community Features

Welcome to Rolling Oaks Phase 5, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Osceola County, Florida. This charming community is designed for those who seek a blend of modern living and tranquil surroundings, making it the perfect place to call home.

Rolling Oaks Phase 5 features a delightful array of homes that cater to a variety of lifestyles, from young families to retirees. Each residence is thoughtfully crafted, showcasing contemporary designs and quality finishes that ensure comfort and style. With spacious layouts and beautiful outdoor spaces, these homes are ideal for entertaining or simply enjoying the serene Florida weather.

One of the standout features of Rolling Oaks Phase 5 is its commitment to community living. Residents can take advantage of a variety of community amenities, including lush green spaces, walking trails, and recreational facilities. The neighborhood fosters a strong sense of camaraderie, making it easy to connect with neighbors and create lasting friendships.

Adding to the allure of this subdivision is its proximity to local dining options. With a variety of restaurants nearby, residents can indulge in diverse culinary experiences without straying far from home. From casual eateries to upscale dining, Rolling Oaks Phase 5 offers a lifestyle that balances convenience and leisure.

Whether you're looking for a peaceful retreat or a vibrant community, Rolling Oaks Phase 5 in Kissimmee is the perfect place to start your next chapter. Come discover the charm and warmth of this exceptional subdivision, where your dream home awaits!

Newest Rolling Oaks Ph 5 Homes with Restaurant Community Features

$315,000

1 Beds ⋅ 1 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

Welcome to Pirate Way — a beautifully furnished 1-bedroom cottage located in the heart of Margaritaville Resort Orlando! If you've been dreaming of owning your own piece of paradise, this charming, turnkey cottage offers the perfect combination of vacation-home lifestyle, resort living and investment potential. Step inside and you'll immediately feel the Margaritaville vibe. This fully furnished, one-story cottage features ceiling fans throughout, a bright and colorful coastal-inspired design, and an open-concept kitchen that flows seamlessly into the living area — perfect for relaxing after a day at the parks or entertaining family and friends and NO carpet! Step outside to your private back patio, complete with a table and four chairs plus two lounge chairs — the perfect spot to enjoy your morning coffee or unwind after a day of fun. And then there's the LOCATION! This cottage is ideally positioned within Margaritaville Resort Orlando, just steps from the resort's incredible amenities. Enjoy access to 7 resort pools, the Fins Up Beach Club, fitness center, resort transportation and shuttle service to the theme parks. The community is also pet-friendly and features Barkaritaville, a dedicated dog park. When you're ready to venture out, you're surrounded by everything that makes this area one of Central Florida's most desirable vacation destinations. Sunset Walk is just steps away, offering restaurants, bars, live entertainment, shopping and more, while Island H2O Water Park is right nearby. Disney, Universal, SeaWorld and Orlando's other major attractions are all just minutes away. Even better, the monthly HOA includes high-speed internet, cable, phone service, daily doorstep trash pickup, landscaping, pest control, a resort shuttle and a shuttle to the parks adding even more convenience to resort living. Whether you're looking for a vacation getaway, second home, full-time residence or a short-term rental investment, this is your opportunity to own a fully furnished cottage in one of Central Florida's most popular resort communities. Pack your flip-flops and come see why life really is better in Margaritaville! Schedule your private showing today!

3054 Pirate Way, Kissimmee

$1,349,000

8 Beds ⋅ 9 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

JUST REDUCED $50,000! NOW IS THE TIME! Kick back and embrace the laid-back island rhythm at this breezy lakefront retreat in Margaritaville Resort Orlando, perfectly positioned on Parrot Head Place. Wrapped in carefree Key West charm, this home delivers sun-splashed interiors, coastal hues, and a relaxed, barefoot-friendly layout that makes every day feel like vacation. Out back, your private pool and spa overlook tranquil water views, creating the ultimate setting for lazy mornings, afternoon floats, and sunset cocktails with a soundtrack of good vibes (NEW POOL HEATER FEB 2026). The open living spaces flow effortlessly for easy entertaining, while spacious bedrooms provide a calm, salt-air escape after long days of fun and sun. Perfectly located just minutes from Walt Disney World, Universal Orlando Resort, including the highly anticipated Universal Epic Universe, and SeaWorld Orlando, this home offers the best of both worlds—action-packed adventures by day and laid-back island living by night. Whether you’re chasing thrills, fireworks, or unforgettable family memories, you’ll love coming home to your own private oasis where the pace slows, the music softens, and relaxation takes center stage. Designed for both personal enjoyment and short-term rental success, this home captures the essence of island living with a splash of luxury. Just steps from resort amenities, dining, and entertainment, it’s a place where worries drift away, flip-flops are the dress code, and life moves at a perfectly unhurried pace. Multiple tropical pools with cabanas, lounging areas, and full food & beverage service. Island-inspired restaurants, poolside bars, and casual spots all within walking distance. The St. Somewhere Spa offers massages, facials, body treatments, and salon services. Find your latitude, adjust your attitude, and come home to a true five-o’clock-somewhere lifestyle—complete with lake views, poolside living, and pure Margaritaville Magic! Sale is contingent upon Buyer entering into a property management agreement with Vstays Property Management and assuming and honoring all existing future reservations/bookings.

3052 Parrot Head Place, Kissimmee

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