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

Welcome to Margaritaville at Rolling Oaks, a delightful subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This enchanting community is designed for those seeking a unique blend of relaxation and adventure, inspired by the laid-back lifestyle of tropical paradise.

Margaritaville at Rolling Oaks offers an inviting collection of beautifully crafted homes, perfect for families, retirees, or anyone yearning for a tranquil escape. This gated community, though lacking a guard, provides residents with an added layer of security and peace of mind. The lush landscaping and thoughtfully designed streets create a warm and friendly atmosphere, making it easy for neighbors to connect and form lasting friendships.

One of the standout features of Margaritaville is its proximity to the world-renowned attractions of Orlando, including Walt Disney World, Universal Studios, and a plethora of shopping and dining options. After a day of adventure, residents can return to their serene retreat, where they can unwind by the community pool, enjoy a leisurely stroll along the scenic pathways, or gather with friends at the clubhouse.

Margaritaville at Rolling Oaks isn't just a place to live; it's a lifestyle choice that embraces the joys of leisure and the spirit of community. With its charming homes and inviting atmosphere, this subdivision is the perfect destination for those looking to experience the best of Florida living. Come discover your slice of paradise in Kissimmee today!

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

$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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