Margaritaville, Rolling Oaks Real Estate

Margaritaville, Rolling Oaks Real Estate

Welcome to Margaritaville in Rolling Oaks, a vibrant subdivision nestled in the heart of Kissimmee, Florida. This delightful community captures the essence of laid-back living while offering a plethora of modern amenities that cater to both relaxation and recreation.

Margaritaville is inspired by the carefree spirit of island life, providing residents with a unique blend of tropical charm and contemporary comforts. With beautifully designed homes that reflect a coastal aesthetic, this subdivision is perfect for those seeking a serene escape or a lively social atmosphere. Each residence is thoughtfully crafted, featuring open floor plans, spacious living areas, and outdoor spaces ideal for entertaining or simply soaking up the Florida sunshine.

Living in Rolling Oaks means you’re just moments away from the magical allure of Kissimmee. Enjoy the convenience of nearby shopping, dining, and entertainment options, including world-renowned theme parks that make Central Florida a sought-after destination. The location also offers easy access to beautiful lakes, nature trails, and parks, perfect for outdoor enthusiasts and families alike.

What truly sets Margaritaville apart is its sense of community. Residents can partake in various social activities, from poolside gatherings to neighborhood events, fostering connections and friendships that last a lifetime. Whether you're looking for a vacation home, a retirement haven, or a family residence, Margaritaville in Rolling Oaks promises a lifestyle that's as vibrant and inviting as its name suggests. Come discover your piece of paradise in Kissimmee, where every day feels like a getaway!

Newest Listings in Margaritaville, Rolling Oaks

8201 Surf Street, Kissimmee
$299,999
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
2916 On The Rocks Point, Kissimmee
$344,999
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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