Margaritaville, Rolling Oaks Homes with Gated Community - No Guard Community Features

Welcome to Margaritaville in Rolling Oaks, a vibrant and enchanting subdivision nestled in the heart of Kissimmee, Florida. This stunning community offers a unique blend of relaxation and adventure, making it the perfect haven for families, retirees, and everyone in between.

Margaritaville is renowned for its laid-back atmosphere, inspired by the tropical vibes of the famous Jimmy Buffett lifestyle. Here, you’ll find beautifully designed homes that embody the spirit of island living, featuring modern amenities and charming architectural details. Each residence is thoughtfully crafted, ensuring comfort and style, whether you're looking for a cozy retreat or a spacious family home.

One of the standout features of this community is its gated access, providing residents with an added layer of security and peace of mind. Although there is no guard at the gate, the controlled entry fosters a friendly and safe environment where neighbors can connect and enjoy the surroundings.

The community boasts a wealth of amenities, including lush green spaces, walking trails, and recreational facilities that encourage an active lifestyle. Spend your weekends lounging by the pool, enjoying a leisurely stroll, or gathering with friends at one of the many community events.

Situated in Osceola County, Kissimmee offers an array of attractions just a stone's throw away, from world-class theme parks to scenic lakes and nature reserves. With its ideal location and inviting ambiance, Margaritaville in Rolling Oaks is not just a place to live; it’s a way of life. Come discover your slice of paradise today!

Newest Margaritaville, Rolling Oaks Homes with Gated Community - No Guard Community Features

$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

$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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