Rolling Oaks Ph 5 Homes with Restaurant Community Features

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

Rolling Oaks Phase 5 is characterized by its beautifully designed homes, each exuding charm and comfort. With a variety of architectural styles, there’s something for every taste, whether you prefer a cozy single-family home or a spacious two-story residence. The thoughtfully planned layouts provide ample space for relaxation and entertaining, while the lush landscaping adds to the neighborhood's appeal.

One of the standout features of Rolling Oaks Phase 5 is its community-centric atmosphere. Residents enjoy access to a variety of amenities, including a delightful on-site restaurant that fosters a sense of togetherness. Imagine savoring delicious meals just a stone’s throw from your front door, perfect for casual dining or special celebrations with friends and family.

Beyond the culinary delights, the community also boasts well-maintained parks and recreational areas, offering opportunities for outdoor activities, social gatherings, and leisurely strolls. The proximity to local attractions, shopping centers, and schools enhances the appeal of this subdivision, ensuring that everything you need is within reach.

Experience the charm of Rolling Oaks Phase 5, where comfortable living meets community spirit in the heart of Kissimmee. Discover your dream home today in this inviting and vibrant neighborhood!

Newest Rolling Oaks Ph 5 Homes with Restaurant Community Features

$311,799

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

Welcome to Pirate Way — a beautifully furnished, fun 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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