Margaritaville, Rolling Oaks Townhomes for Sale

Welcome to Margaritaville, Rolling Oaks – a vibrant subdivision nestled in the heart of Kissimmee, Florida, within beautiful Osceola County. This delightful community is designed for those seeking a perfect blend of relaxation and adventure, embodying the spirit of island living right in your own backyard.

Margaritaville is renowned for its laid-back lifestyle, inspired by the tropical vibes of Jimmy Buffett. Here, you can unwind in a stunning townhome that offers modern amenities, stylish designs, and an inviting atmosphere. Each townhome for sale is meticulously crafted, featuring spacious layouts, gourmet kitchens, and private outdoor spaces ideal for enjoying the warm Florida sunshine.

Living in Rolling Oaks means you’re just moments away from world-class attractions. Explore the magic of Walt Disney World, bask in the sun at nearby beaches, or indulge in shopping and dining at local hotspots. The community also boasts a range of amenities, including resort-style pools, fitness centers, and beautifully landscaped parks, ensuring there’s always something to do.

Whether you’re looking for a vacation home or a permanent residence, the townhomes in Margaritaville, Rolling Oaks offer a unique opportunity to embrace a lifestyle filled with fun, relaxation, and adventure. Experience the charm of this community and discover why it’s the perfect place to call home in Kissimmee, Florida. Don’t miss out on your chance to own a piece of paradise – explore the available townhomes for sale 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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