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 vibrant Osceola County. This charming community is designed for those who seek a serene lifestyle without sacrificing convenience. With its picturesque landscapes and well-manicured lawns, Rolling Oaks Phase 5 offers a perfect blend of comfort and elegance.

Homes in Rolling Oaks Phase 5 are a testament to modern living, featuring contemporary designs that cater to various tastes and preferences. Each residence is thoughtfully crafted with spacious floor plans, high-end finishes, and ample natural light, creating an inviting atmosphere for families and individuals alike. Whether you're looking for a cozy retreat or a spacious family home, you'll find a variety of options to suit your needs.

One of the standout features of Rolling Oaks is its gated amenities, which provide an added layer of security and peace of mind. Residents can enjoy exclusive access to beautifully maintained recreational facilities, including a sparkling community pool, fitness center, and lush green spaces perfect for leisurely strolls or picnics with loved ones. The gated entrance ensures that you can relax and enjoy your surroundings, knowing that your community is safe and secure.

Located just minutes away from the bustling attractions of Kissimmee, including shopping, dining, and entertainment options, Rolling Oaks Phase 5 offers the perfect balance of tranquility and accessibility. Experience the best of Florida living in this delightful community, where your dream home awaits!

Newest Rolling Oaks Ph 5 Homes with Gated 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

Start Your Search