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

Welcome to Margaritaville in Rolling Oaks, a captivating subdivision nestled in the heart of Kissimmee, Florida. This vibrant community offers a unique blend of relaxation and excitement, making it the perfect place for families, retirees, or anyone looking to enjoy the best of Florida living.

Margaritaville is designed with a laid-back, tropical vibe, reminiscent of the carefree spirit of island life. The homes here are thoughtfully crafted, featuring modern amenities and charming designs that reflect the essence of paradise. Each residence is nestled within a gated community, providing residents with peace of mind and a sense of security, without the need for a guard on duty. This means you can enjoy the tranquility of your surroundings while knowing your privacy is respected.

The community itself is brimming with features that enhance the Margaritaville lifestyle. Imagine leisurely strolls along scenic pathways, vibrant landscaping, and inviting communal spaces perfect for gatherings with friends and family. Residents can take advantage of nearby recreational facilities, including pools, fitness centers, and walking trails, ensuring a healthy and active lifestyle.

Additionally, Margaritaville’s prime location in Kissimmee places you just a short drive away from world-renowned attractions like Walt Disney World, Universal Studios, and the beautiful beaches of the Florida coast. Whether you’re looking to explore the local culture, indulge in shopping, or embrace the thrill of amusement parks, everything you need is right at your fingertips.

Come discover the magic of Margaritaville in Rolling Oaks, where every day feels like a vacation!

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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