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 hidden gem nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This charming subdivision is perfect for those seeking a serene lifestyle while still being close to the excitement that Central Florida has to offer.

Rolling Oaks Phase 5 boasts beautifully designed homes that cater to a variety of tastes and lifestyles. Each residence is thoughtfully crafted, featuring modern amenities and spacious layouts that invite natural light and comfort into every corner. One of the standout features of this community is its inviting homes with pools, providing the perfect oasis for relaxation and recreation. Imagine spending sunny afternoons lounging by your own private pool, hosting barbecues with family and friends, or enjoying a refreshing dip on warm Florida days.

The community itself is designed with residents in mind, offering a friendly atmosphere where neighbors become friends. With well-maintained streets and lush landscaping, Rolling Oaks Phase 5 exudes charm and warmth. Families will appreciate the proximity to top-rated schools, parks, and recreational facilities, making it an ideal place to raise children.

For those who enjoy the outdoors, Kissimmee is renowned for its beautiful parks and nature trails, as well as its close proximity to world-famous attractions such as Walt Disney World and Universal Studios. Whether you're looking for a peaceful retreat or an active lifestyle, Rolling Oaks Phase 5 offers the perfect blend of comfort, community, and convenience. Come and discover your dream home in this captivating neighborhood!

Newest Rolling Oaks Ph 5 Homes with Pool 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
$399,900
3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
WOW under $400K...FULLY FURNISHED | 3 BEDROOMS + BONUS ROOM | 3 FULL BATHS | DUAL PRIMARY SUITES | PRIVATE HOT TUB | MINUTES FROM DISNEY. A NEW PRICE. A PRIME LOCATION. AN OPPORTUNITY WORTH A SECOND LOOK. Newly offered at $399,900 a fully furnished, turnkey cottage ideally positioned within Margaritaville Resort Orlando and just a short walk to the resort amenities.This property delivers the combination today's vacation-home buyer is searching for: location, flexible accommodations, resort lifestyle and exceptional value near Walt Disney World. Whether you're searching for a Florida vacation home, second residence, short-term rental opportunity or personal getaway with income potential, this home offers versatility in one of Central Florida's most recognizable vacation destinations. The prime corner location immediately sets this cottage apart, while its thoughtfully designed 3-bedroom + bonus-room floor plan with 3 full bathrooms provides flexible space for owners, families and vacationing guests. A standout feature is the DUAL PRIMARY-SUITE DESIGN, with private suites located on BOTH the first and second floors. The first-floor primary offers added convenience and direct access to the outdoor living area, while the second suite creates additional privacy for guests or multigenerational stays. Inside, the bright, open-concept design features soaring ceilings, abundant natural light, quartz countertops, stainless steel appliances, upgraded cabinetry and the sought-after "Son of a Sailor" interior package. The kitchen, dining and living areas flow together beautifully, creating a welcoming central gathering space for entertaining, relaxing and vacation living. Step outside and the Florida lifestyle continues. A private paved patio, tropical landscaping and heated above-ground hot tub create your own outdoor retreat, the perfect place to unwind after a day at Disney, enjoy an evening under the palms or simply escape into vacation mode without leaving home. Even better, IT'S ALL INCLUDED. This home is being offered FULLY FURNISHED AND TURNKEY, including furniture, televisions, artwork, décor, linens, kitchen essentials, window treatments, housewares and more. Skip the expense and hassle of furnishing a vacation property and start enjoying it from day one. And then there's the LOCATION. Situated inside Margaritaville Resort Orlando, you're surrounded by the resort lifestyle while remaining just minutes from Walt Disney World, Universal Orlando, Epic Universe, championship golf, shopping, dining and Central Florida's world-famous attractions. Nearby Sunset Walk adds restaurants, entertainment, live music, shopping and year-round events to the experience.What an exciting opportunity to own a furnished, flexible-layout vacation property in the heart of Orlando's tourism corridor.Dual primary suites. Bonus room. Private hot tub. Fully furnished. Resort lifestyle. Minutes from Disney. Don't just vacation in paradise, OWN IT. Schedule your private showing of 8060 Dreamsicle Drive today.

8060 Dreamsicle Drive, Kissimmee
$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
$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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