Rolling Oaks Ph 5 Homes with Pool Community Features

Rolling Oaks Ph 5 Homes with Pool Community Features

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

Rolling Oaks Phase 5 boasts a collection of beautifully designed homes, many of which feature inviting swimming pools, providing residents with a refreshing oasis right in their backyards. Imagine spending sunny Florida afternoons lounging by your pool, hosting barbecues with friends, or enjoying peaceful evenings under the stars. The poolside lifestyle is not just a luxury; it's a way of life here!

The community itself is designed with family-friendly amenities, ensuring that both residents and visitors can enjoy a variety of recreational activities. Take a leisurely stroll through the scenic streets, where you’ll find lush landscaping and a welcoming neighborhood vibe. The nearby parks and playgrounds are perfect for children to play and explore, while adults can enjoy walking trails and picnic areas.

Located just a short drive away from Kissimmee's vibrant downtown, residents of Rolling Oaks Phase 5 have easy access to shopping, dining, and entertainment options. Plus, with major highways nearby, commuting to Orlando and other surrounding areas is a breeze.

In Rolling Oaks Phase 5, you’ll not only find a home but a community that embraces the Florida lifestyle. Come discover your dream home in this inviting neighborhood, where relaxation meets recreation in a serene setting.

Newest Rolling Oaks Ph 5 Homes with Pool Community Features

$525,000
4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
Welcome to 8060 Dreamsicle Drive, where every day feels like a vacation and every stay creates an opportunity. Located within the world-renowned Margaritaville Resort Orlando, and is just a short walk to the amenities. This beautifully FULLY FURNISHED and income-producing cottage offers the perfect combination of luxury resort living, investment potential, and unforgettable Florida lifestyle experiences, all just minutes from Walt Disney World. Whether you're searching for a high-performing vacation rental, a second home in paradise, or a personal retreat that generates income when you're away, this turnkey property delivers on every level. From the moment you arrive, the charming Key West-inspired architecture, tropical landscaping, and colorful coastal design create an atmosphere that instantly transports you into vacation mode. Inside, you'll discover a thoughtfully designed open-concept floor plan featuring soaring ceilings, abundant natural light, designer finishes, and the highly sought-after "Son of a Sailor" interior package. The beautifully appointed kitchen features quartz countertops, upgraded cabinetry, stainless steel appliances, and ample space for gathering with family and friends after a day of enjoying everything Orlando has to offer. The spacious living and dining areas flow seamlessly together, creating the perfect environment for entertaining, relaxing, and making lasting memories. This home is a 3 bedroom with a bonus room. One of the most desirable features of this home is the rare dual-primary-suite layout, with (2) PRIVATE OWNER'S SUITES located on both the first and second floors, providing exceptional comfort and flexibility for owners and guests alike. Step outside to your private tropical oasis where a beautifully paved patio, lush landscaping, and above-ground hot tub create the perfect setting to unwind under the Florida sunshine or enjoy peaceful evenings after visiting the nearby theme parks. This home is being offered fully furnished and turnkey, including furniture, televisions, artwork, décor, linens, kitchen essentials, window treatments, housewares, and more, allowing the next owner to immediately begin enjoying the property or continue operating it as a successful vacation rental. Beyond the home itself lies one of Central Florida's most exciting resort destinations. Margaritaville Resort Orlando offers a truly unmatched lifestyle experience featuring multiple resort-style pools, fitness center, on-site water park, entertainment venues, concierge services, and access to the vibrant Sunset Walk district featuring restaurants, bars, live music, shopping, nightlife, family attractions, and year-round events. Located just minutes from Disney Parks, Universal Studios, Epic Universe, championship golf courses, Orlando International Airport, shopping, dining, and major highways, this prime location continues to attract vacationers and investors from around the world. Opportunities like this are becoming increasingly rare. Whether your goal is generating rental income, owning a luxury vacation home, building a real estate investment portfolio, or simply embracing the Margaritaville lifestyle. Paradise isn't just a destination, it can be your next address. Schedule your private showing TODAY!

8060 Dreamsicle Drive, Kissimmee
$394,999
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
FULLY FURNISHED AND IMMACULATE!!! This Margaritaville Resort beauty is amazing and has the Ethan Allen Furniture Package. Your back patio has a PERSONAL HOT TUB. With 2-bedrooms, 2.5-baths, it is the perfect blend of luxury, comfort, and unforgettable full-time or vacation living. iIT HAS NEVER BEEN RENTED!! Inside you'll find an inviting open-concept floor plan with upgrades throughout, including wood-look ceramic tile flooring, over- and under-cabinet lighting, and custom backsplash and island kickplate tiling in the kitchen. The open living area has in-ceiling speakers, a Klipsch soundbar, Samsung Frame TV, and a queen sleeper sofa for extra guests. Each of the two spacious bedrooms has a large flat screen TV and its own private ensuite bathroom, providing comfort and privacy for owners and guests alike.  The primary suite has a walk-in closet and its own balcony for morning views and coffee, and the second bedroom also has its very own balcony as well, making it the perfect place to unwind while enjoying breathtaking views. Your back patio is designed for ultimate outdoor living. You can enjoy the tranquil park views or relax in your very own hot tub. Your patio area is ideal for entertaining or relaxing after a day at work or the fun day at the parks with a patio table, chairs and sun loungers, giving you endless possibilities to create your own private oasis.  Whether you’re looking for a luxury vacation home, investment property, or a personal retreat, this rare offering delivers the best resort-style living just minutes from world-class attractions, dining, and entertainment. Sunset Walk is located within the resort and is filled with a ton of restaurants, a movie theater, live entertainment, and more. The resort also has H20 Waterpark and a ton of retail which is ALL walkable from this home. HOA and The Fins Up Club cover daily trash removal, internet, cable, phone, pest control, landscaping, free resort shuttle, shuttle to parks, resort pools, and fitness center.

3009 Sea Plane Lane, Kissimmee
$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
$1,375,000
8 Beds ⋅ 9 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
'EASY BREEZY' Cottage on Margaritaville Resort Orlando's 'TROPHY ROW'! EXTREMELY RARE OPPORTUNITY TO OWN ONE of the LARGEST WATERFRONT COTTAGES WITH POOL and SPA Plus Your Very Own ELEVATOR ($40k Upgrade)! Home is FULLY HANDICAP ACCESSIBLE. 4131-A Model, 8 Bedrooms, 8 Full Bathrooms and 1 Half Bathroom with IN PARADISE Upgrade. This Amazing Home Features One En Suite Bedroom on First Floor Along with Another Bedroom with Hallway Bath, Large Kitchen with Tiled Backsplash and Breakfast Bar, Spacious Pantry with CUSTOM SHELVING, Living Room with Sliders that Lead to Beautiful Paved Patio, Fenced In Backyard has Covered Area, Cabana Bath, Outdoor Speakers and TV Hookup, In-Ground Pool and Spa with Custom Safety Handrails and Spectacular SUNSET VIEWS Over the Pond! Second Floor has Primary Suite with Separate Tub and Shower, CUSTOM BUILT CLOSET and Access to Balcony Overlooking Backyard. Three En Suite Bedrooms Complete Second Floor with Hallway Access to the Large Front Balcony. Third Floor has Upgraded Mosaic Tiled Alcoves which Compliment the Stairs leading to a Suite with Separate Tub and Shower, Access to Huge Tiled and COVERED PARTY DECK with Sweeping Lake Views. Loft with Wet Bar is Next to the Eighth Bedroom with Full Bathroom. Home also has Covered Front Porch, Upgraded 'Wood' Tile Flooring, Quartz Countertops. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! LOCATED MINUTES FROM DISNEY PARKS! There's Nothing Like Living the Margaritaville Lifestyle in Paradise!

3056 Parrot Head Place, Kissimmee
Start Your Search