Rolling Oaks Ph 5 Homes with Playground Amenities

Welcome to Rolling Oaks Phase 5, a hidden gem nestled in the heart of Kissimmee, Florida. This charming subdivision is a perfect blend of serene living and vibrant community life, making it an ideal choice for families, retirees, and everyone in between. Rolling Oaks Phase 5 is not just a place to live; it’s a lifestyle.

As you explore this delightful community, you’ll be captivated by the beautiful homes that boast modern designs and spacious interiors. Each residence is thoughtfully crafted to offer comfort and style, ensuring that every family member feels right at home. The neighborhood is known for its friendly atmosphere, where neighbors become friends and community spirit thrives.

One of the standout features of Rolling Oaks Phase 5 is its family-friendly amenities, particularly the well-maintained playgrounds that invite laughter and joy. These playgrounds are perfect for children to play, explore, and make lasting memories, while parents can relax knowing their little ones are in a safe and engaging environment. The open spaces and green areas provide plenty of room for outdoor activities, picnics, and community gatherings.

Located in Osceola County, Kissimmee is renowned for its proximity to world-class attractions, shopping, and dining options, making Rolling Oaks Phase 5 a convenient haven for those who love to explore. With easy access to major highways, residents can enjoy the best that Central Florida has to offer, from the magic of Disney to the tranquility of nearby parks.

Discover the charm of Rolling Oaks Phase 5, where community, comfort, and convenience come together to create the perfect place to call home.

Newest Rolling Oaks Ph 5 Homes with Playground Amenities

$329,900

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

SELLER MOTIVATED - CALL FOR YOUR PRIVATE SHOWING TODAY! 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

$1,399,000

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

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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