Rolling Oaks Ph 5 Homes with Maintenance Free Community Extras

Rolling Oaks Ph 5 Homes with Maintenance Free Community Extras

Welcome to Rolling Oaks Phase 5, a picturesque subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming community is designed for those who appreciate the perfect blend of tranquility and modern living. Rolling Oaks Phase 5 offers an idyllic lifestyle where maintenance-free living meets the beauty of nature, making it an exceptional choice for families, retirees, and everyone in between.

One of the standout features of Rolling Oaks Phase 5 is its commitment to providing a maintenance-free living experience. Residents can enjoy beautifully landscaped common areas without the hassle of upkeep, allowing more time to relish the community's amenities and nearby attractions. Imagine spending your weekends exploring the lush parks, engaging in outdoor activities, or simply relaxing in your well-appointed home without the worry of yard work.

The homes in Rolling Oaks Phase 5 are thoughtfully designed to cater to a variety of tastes and lifestyles, featuring modern layouts, spacious interiors, and high-quality finishes. Whether you’re looking for a cozy retreat or a place to host family gatherings, you’ll find a residence that feels just right.

With its prime location in Kissimmee, residents have easy access to a wealth of shopping, dining, and entertainment options, along with the enchanting allure of Central Florida’s famous attractions, including the magic of Walt Disney World and the natural beauty of local parks.

Discover the charm and convenience of Rolling Oaks Phase 5—a community where you can truly enjoy the best of Florida living!

Newest Rolling Oaks Ph 5 Homes with Maintenance Free Community Extras

$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
Start Your Search