Rolling Oaks Ph 5 Homes with Pool Community Features

Rolling Oaks Ph 5 Homes with Pool Community Features

Welcome to Rolling Oaks Phase 5, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the beautiful Osceola County. This vibrant community is an ideal blend of comfort, convenience, and charm, making it a perfect place for families, retirees, and everyone in between to call home.

Rolling Oaks Phase 5 boasts a collection of stunning homes, many of which feature private pools, offering a refreshing oasis right in your backyard. Imagine basking in the Florida sunshine while enjoying a leisurely swim or hosting unforgettable barbecues with family and friends. The poolside lifestyle is not just a luxury here; it’s a way of life that enhances your living experience.

The community is thoughtfully designed with a variety of amenities that cater to your every need. Lush, landscaped common areas invite you to stroll or jog, while playgrounds and recreational spaces provide ample opportunities for outdoor fun and socializing. With a strong sense of community, neighbors often gather for events and activities, fostering friendships that last a lifetime.

Conveniently located, Rolling Oaks Phase 5 offers easy access to major highways, shopping centers, dining options, and entertainment venues. Whether you’re heading to the magic of Walt Disney World or enjoying the natural beauty of nearby parks, everything you need is just a short drive away.

Discover the beauty and serenity of Rolling Oaks Phase 5, where your dream home with a pool awaits. Experience the perfect blend of suburban tranquility and vibrant community life in this captivating Kissimmee neighborhood!

Newest Rolling Oaks Ph 5 Homes with Pool Community Features

8028 Dreamsicle Drive, Kissimmee
$399,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
BEAUTIFUL and SPACIOUS Cottage For Sale with 2 Bedrooms, 2.5 Bathrooms and a HOT TUB at Margaritaville Resort Orlando! Located in a PREMIUM RESORT LOCATION, Close to the Pedestrian Bridge and just a Short Walk to the Resort Amenities! This HOME IS RENT READY. MRO Approved City Furniture/Housewares Package is INCLUDED IN LIST PRICE! The home features "IN PARADISE" Interior Upgrades, QUARTZ Countertops, Ceiling Fans, Upgraded Appliances, High Ceilings, 'WOOD' Tile Flooring Throughout, TANKLESS WATER HEATER, HIGH CAPACITY Washer and Dryer and a Large Backyard with Paved Patio and Tropical Foliage. Upstairs You Will Find Two En Suite Bedrooms. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES Furniture/Housewares with 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, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

8028 Dreamsicle Drive, Kissimmee
8036 Surf Street, Kissimmee
$470,000
4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
BEST PARKVIEW BACKYARD IN THE ENTIRE RESORT WITH GRASS! NOTHING ELSE COMPARES! '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
8060 Dreamsicle Drive, Kissimmee
$399,900
3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code
YOUR ORLANDO VACATION HOME IS READY—JUST BRING YOUR SUITCASE! Fully furnished and turnkey inside Margaritaville Resort Orlando, this 3-bedroom + BONUS ROOM, 3-bath cottage delivers the resort lifestyle buyers dream about just minutes from Walt Disney World. A desirable CORNER LOCATION and DUAL PRIMARY SUITES one upstairs and one downstairs, create exceptional flexibility for owners, families, and vacationing guests. Inside, soaring ceilings and abundant natural light complement the open-concept design, quartz countertops, stainless steel appliances, upgraded cabinetry, and signature “Son of a Sailor” interior package. Step outside to your private tropical retreat featuring a paved patio and HEATED HOT TUB, the perfect ending to a day at the parks.Best of all, it’s FULLY FURNISHED, including furniture, TVs, décor, linens, kitchen essentials, housewares, and more. Enjoy it immediately as your Florida getaway, second home, or SHORT-TERM RENTAL opportunity. Walk to Margaritaville resort amenities and enjoy nearby Sunset Walk dining, shopping, entertainment, and live music. Minutes from Disney, Universal Orlando, Epic Universe, golf, and Central Florida attractions. Don’t just visit paradise...OWN IT.

8060 Dreamsicle Drive, Kissimmee
3054 Pirate Way, 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
3052 Parrot Head Place, 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
3056 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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