Rolling Oaks Ph 5 Homes with Gated Amenities

Welcome to Rolling Oaks Phase 5, an exquisite subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This charming community offers a perfect blend of tranquility and modern living, making it an ideal choice for families, retirees, and everyone in between.

As you enter Rolling Oaks Phase 5, you are greeted by a beautifully gated entrance, providing not only security but also a sense of exclusivity. The meticulously landscaped surroundings create an inviting atmosphere, where neighbors become friends and community spirit thrives. The subdivision is designed with family-friendly features, including spacious parks, walking trails, and recreational areas, perfect for enjoying Florida's sunny weather.

The homes in Rolling Oaks Phase 5 are thoughtfully designed with modern amenities and stylish finishes, catering to a variety of lifestyles. Whether you're looking for a cozy single-family home or a more spacious residence, this community has something for everyone. Many of the homes boast open floor plans, gourmet kitchens, and private backyards, creating the perfect sanctuary for relaxation and entertaining.

Living in Rolling Oaks Phase 5 means you are just a stone's throw away from the vibrant attractions of Kissimmee. Enjoy nearby shopping, dining, and entertainment options, as well as quick access to the magic of Walt Disney World and other renowned attractions.

If you're seeking a serene yet vibrant community with gated amenities, Rolling Oaks Phase 5 is the perfect place to call home. Discover the charm of this unique subdivision and make your dream of Florida living a reality!

Newest Rolling Oaks Ph 5 Homes with Gated Amenities

$315,000

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

LOCATION! LOCATION! LOCATION! This spectacular, FULLY FURNISHED home is not only centrally located and with in 20 mins of all Disney Parks, but it is also perfectly located within the resort, just feet away from the amenitities including the pool, spa abd fitness center. It features tile flooring and ceiling fans throughout. It is a 1 story, 1 bedroom and 1 bath fully furnished cottage, beautifully themed, bright and colorfully decorated. The kitchen opens seamlessly to the main living area, making it perfect for entertaining or vacation hosting. The back patio includes a table and 4 chairs as well as 2 sun loungers, Margaritaville is a pet-friendly community, which also features Barkaritaville, a great dog park. The monthly HOA covers high-speed internet, cable, phone, daily doorstep garbage pickup, professional landscaping, and pest control. The Fins UP Beach Club gives you access to enjoy full access to world-class resort amenities including 7 resort pools, a fitness center/gym, an internal resort shuttle, and free transportation shuttles directly to the local theme parks. This unique resort setup is highly walkable, situated just steps from Island H2O Water Park and Sunset Walk’s vibrant mix of restaurants, bars, live music, Target, Ulta and more. Centrally located with lightning-fast access to Disney, Universal, SeaWorld, and Gatorland, this property is a premier choice for a primary residence, second home, or lucrative vacation investment.

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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