Margaritaville, Rolling Oaks Townhomes for Sale

Welcome to Margaritaville, Rolling Oaks – a vibrant and enchanting subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This captivating community is a true paradise for those seeking a blend of relaxation, adventure, and the quintessential Florida lifestyle.

Margaritaville is renowned for its laid-back atmosphere, inspired by the carefree spirit of island living. The Rolling Oaks section features an array of beautifully designed townhomes that cater to both families and individuals looking for a serene escape. Each townhome is thoughtfully crafted with modern amenities, spacious layouts, and stunning finishes, providing the perfect backdrop for both entertaining and unwinding.

Living in Margaritaville means embracing a lifestyle filled with leisure and recreation. Residents enjoy access to a plethora of on-site amenities, including resort-style pools, a state-of-the-art fitness center, and lush walking trails that wind through the community. The vibrant atmosphere is further enhanced by nearby attractions, including world-famous theme parks, shopping destinations, and exquisite dining options, all just a stone's throw away.

Whether you are looking for a permanent residence, a vacation home, or an investment opportunity, the townhomes for sale in Margaritaville, Rolling Oaks, offer a unique chance to experience Florida living at its finest. Imagine waking up to the gentle sounds of nature and the warm Florida sun streaming through your windows. This is not just a home; it’s a lifestyle waiting for you to embrace. Come discover your slice of paradise in Margaritaville today!

Newest Margaritaville, Rolling Oaks Townhomes for Sale

$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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