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

Welcome to Margaritaville at Rolling Oaks, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida. This charming community is perfectly situated in Osceola County, where sunshine and warmth are a way of life. Margaritaville offers a unique blend of relaxation and excitement, making it an ideal destination for families, retirees, and anyone looking to embrace the Florida lifestyle.

As you enter this gated community, you’ll immediately feel the sense of security and tranquility that comes with living in a no-guard community. The beautifully landscaped surroundings create a picturesque setting, with lush greenery and tropical vibes that echo the spirit of paradise. Whether you’re strolling through the well-maintained pathways or enjoying a leisurely afternoon by the community pool, every moment spent here is a reminder of why you chose to call Margaritaville home.

The homes in Margaritaville at Rolling Oaks are designed with comfort and style in mind. Featuring spacious layouts and modern amenities, these residences cater to a variety of lifestyles. From cozy retreats to expansive family homes, there’s something for everyone in this delightful community.

Residents enjoy access to a range of amenities that enhance the living experience, including parks, recreational areas, and convenient shopping options just a stone's throw away. With the vibrant attractions of Kissimmee and the allure of nearby Disney World, adventure is always at your fingertips.

Discover the charm of Margaritaville at Rolling Oaks, where every day feels like a vacation. Embrace the Florida lifestyle and make this captivating community your new home!

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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