Margaritaville, Rolling Oaks Homes with Stucco Exterior Construction

Welcome to Margaritaville, Rolling Oaks – a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida, in beautiful Osceola County. This charming community embodies the spirit of laid-back living, where every day feels like a vacation. With its tropical ambiance and lush surroundings, Margaritaville is the perfect place to call home.

The homes in Rolling Oaks are designed with a keen eye for detail, featuring stunning stucco exterior construction that not only enhances their aesthetic appeal but also provides durability against Florida's weather. These homes are built to last, offering a perfect blend of style and functionality. With spacious layouts and modern amenities, they cater to families, retirees, and anyone looking to embrace the Florida lifestyle.

Imagine waking up in a beautiful stucco home, with the sun shining and palm trees swaying gently outside your window. The community is designed for those who appreciate a relaxed atmosphere, with access to resort-style amenities, including sparkling pools, lush walking trails, and social gathering spaces. Whether you’re enjoying a leisurely afternoon by the pool or exploring the nearby attractions, Margaritaville offers a lifestyle that is both vibrant and serene.

Located just minutes from the world-renowned theme parks and attractions of Orlando, as well as the stunning beaches of the Atlantic coast, Rolling Oaks provides the perfect balance of excitement and tranquility. Discover the charm of Margaritaville, where your dream home awaits in this delightful subdivision. Come and experience the best of Florida living!

Newest Margaritaville, Rolling Oaks Homes with Stucco Exterior Construction

$315,000

2 Beds ⋅ 3 Baths ⋅ Margaritaville, Rolling Oaks SubDv. ⋅ 34747 Zip Code

Welcome to paradise at 8201 Surf St, a beautifully appointed, fully furnished 2-bedroom, 2.5-bathroom townhome offering the ultimate turn-key resort lifestyle. Nestled in the heart of the world-class Margaritaville Resort Orlando, this property boasts a prime location on the same street as the signature cottages and stands as one of the closest units to the main hotel building and its sprawling resort-style pool complex. Step inside to an inviting, open-concept floor plan filled with tropical charm and modern finishes, seamlessly extending out to a private patio area perfect for enjoying warm Florida sunshine, morning coffee, or evening relaxation. Positioned for exceptional investment potential, this home generated $45,587.00 in rental revenue for 2025, making it a proven performer for savvy real estate investors or buyers seeking an income-producing personal vacation getaway. Owners and guests enjoy top-tier resort amenities, including the zero-entry pools at Fins Up Beach Club, the tranquil St. Somewhere Spa, poolside dining at Salty Rim Bar & Grill, a state-of-the-art fitness center, and access to the adjacent Promenade at Sunset Walk and Island H2O Water Park. Located just minutes from Walt Disney World, Universal Orlando, premier shopping, and world-class dining, this move-in-ready property delivers effortless island living and lucrative return potential in Central Florida’s premier destination.

8201 Surf Street, Kissimmee

$359,999

3 Beds ⋅ 3 Baths ⋅ Margaritaville, Rolling Oaks SubDv. ⋅ 34747 Zip Code

Welcome to paradise at 2916 On The Rocks Pt, a stunning, turnkey-ready 3-bedroom, 3-bathroom townhome located in the highly coveted Margaritaville Resort Orlando. Sold fully furnished and beautifully decorated, this property features a bright, open-concept living area that seamlessly transitions to your own private patio space—perfect for soaking in the warm Florida sunshine. Best of all, you are just steps away from one of the pristine community pools. Designed for effortless ownership, this property is an exceptional opportunity for vacation home buyers seeking a personal tropical getaway or savvy investors looking to capitalize on a premier short-term rental destination. Living in Margaritaville Resort means enjoying a world-class, island-inspired lifestyle with access to incredible amenities, including expansive lagoon-style swimming pools, the relaxing St. Somewhere Spa, a state-of-the-art fitness center, and the thrilling Island H2O Water Park. The property is also exceptionally close to the Promenade at Sunset Walk, a bustling hub packed with premier dining, retail shopping, and live entertainment. Located just minutes away from Walt Disney World Resort and other top Central Florida attractions, this townhome offers the ultimate blend of resort relaxation and theme park adventure.

2916 On The Rocks Point, Kissimmee

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