Rolling Oaks Ph 5 Homes with Street Lights Community Features

Rolling Oaks Ph 5 Homes with Street Lights Community Features

Welcome to Rolling Oaks Phase 5, a charming subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This vibrant community is perfect for families and individuals seeking a serene yet connected lifestyle, offering a perfect blend of suburban tranquility and urban convenience.

Rolling Oaks Phase 5 features beautifully designed homes that cater to a variety of tastes and preferences. Whether you’re looking for a cozy single-family home or a spacious abode for your growing family, you’ll find an array of options that suit your needs. Each residence is thoughtfully crafted with modern amenities and stylish finishes, ensuring comfort and functionality for every homeowner.

One of the standout features of Rolling Oaks is its well-planned layout, complete with inviting street lights that enhance the community's charm and safety. Evening strolls become a delightful experience as the soft glow of street lights illuminates the pathways, creating a warm and welcoming atmosphere for residents and their guests.

In addition to its aesthetic appeal, Rolling Oaks Phase 5 is strategically located near major highways, shopping centers, and recreational facilities, making it easy for residents to enjoy all that Kissimmee has to offer. From vibrant local dining options to beautiful parks and outdoor activities, there’s never a shortage of things to do in this lively area.

Discover the enchanting lifestyle that awaits you in Rolling Oaks Phase 5, where community spirit thrives, and every day feels like a retreat. Come home to a place where comfort meets convenience, and let your new chapter begin!

Newest Rolling Oaks Ph 5 Homes with Street Lights Community Features

$470,000
4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
'PIRATES IN PARROTDISE' Cottage at Margaritaville Resort Orlando! Spacious Model 1384-C with 3 Bedrooms, 3 Bathrooms and an ADDITIONAL BONUS BEDROOM, BACK PATIO RETRACTABLE AWNING and a HOT TUB! Premium Location Near the Pedestrian Bridge! Spacious Living Room has a HUGE 75-INCH TV. IMMACULATE CONDITION ~ WELL MAINTAINED HOME. This home has NEVER been an STR and has been used as a SECOND HOME and LONG-TERM RENTAL most recently. First Floor Bedroom has En-Suite Bathroom and French Doors Leading to Spacious Backyard Patio with a Gorgeous GRASSY Backyard and TIKI HUTS. Second Floor has Primary En-Suite Bedroom with Front Balcony Access. Bonus Room has been Converted to a Bunk Room. The Kitchen features Upgraded Appliances, and Quartz Countertops. This Home also features Tile Flooring, Ceiling Fans Throughout, Washer and Dryer, Landscaping has Beautiful Foliage! All Furniture, Linens, Housewares and Decor INCLUDED IN LIST PRICE! Includes HIGH END ETHAN ALLEN FURNISHINGS, Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, Linens, and so MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! LOCATED MINUTES FROM DISNEY PARKS! Come Enjoy the Margaritaville Lifestyle in Paradise!

8036 Surf Street, Kissimmee
$394,999
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
YOUR PRIVATE PIECE OF PARADISE IN MARGARITAVILLE! Fully furnished, beautifully upgraded, and complete with your own private hot tub, 3009 Sea Plane Lane is the Margaritaville vacation home you've been waiting for! This stunning 2-bedroom, 2.5-bath cottage combines the carefree Margaritaville lifestyle with thoughtful upgrades, beautiful furnishings and a private outdoor retreat. From the moment you walk in, you'll notice the difference. This home features the Ethan Allen furniture package, wood-look ceramic tile flooring, high ceilings, upgraded lighting, and a beautifully designed kitchen with custom backsplash and island details, plus convenient over- and under-cabinet lighting. The open-concept living area is made for relaxing and entertaining, featuring in-ceiling speakers, a Klipsch soundbar, Samsung Frame TV and a queen sleeper sofa for additional guests. The home is being offered fully furnished, making it truly turnkey for your next vacation getaway, second home or investment property. Step through the kitchen and into your private backyard oasis! The spacious paver patio features a personal hot tub, lounge chairs and lush tropical landscaping, creating a peaceful and private space to unwind after a day at the parks or enjoy an evening under the Florida sky. Upstairs, you'll find two comfortable bedrooms and two full bathrooms, providing plenty of privacy for owners and guests. The thoughtful layout makes this home equally appealing for personal use or vacation rental opportunities. And then there's the location! You are inside Margaritaville Resort Orlando, surrounded by everything that makes this community one of Central Florida's most sought-after vacation destinations. Sunset Walk is right within the resort, offering restaurants, bars, live entertainment, shopping and a movie theater. Island H2O Water Park is also walkable, while Disney, Universal and Orlando's world-famous attractions are just minutes away. Resort amenities include multiple pools, fitness facilities, dog park, resort transportation and shuttle service to the theme parks. The HOA/Fins Up Club also includes services such as internet, cable, phone, landscaping, pest control and daily trash removal, making ownership incredibly convenient. Whether you're looking for a luxury vacation home, a second home, a full-time Florida residence or a vacation rental investment, this turnkey Margaritaville cottage gives you the opportunity to own the lifestyle everyone comes to Central Florida to enjoy. Private hot tub. Designer furnishings. Resort amenities. Sunset Walk. Theme parks. Margaritaville. Come see why life really is better in Margaritaville! Schedule your private showing today.

3009 Sea Plane Lane, Kissimmee
$315,000
1 Beds ⋅ 1 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
Welcome to Pirate Way — a beautifully furnished 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
$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
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