Margaritaville, Rolling Oaks Homes with Sidewalks Community Features

Margaritaville, Rolling Oaks Homes with Sidewalks Community Features

Welcome to Margaritaville in Rolling Oaks, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida. This picturesque community, located in Osceola County, offers a perfect blend of relaxation and recreation, embodying the laid-back lifestyle that Florida is renowned for.

Margaritaville is not just a place to live; it’s a lifestyle choice. This charming neighborhood features beautifully designed homes with sidewalks, encouraging leisurely strolls and fostering a sense of community among residents. Picture yourself taking evening walks, greeting neighbors, and enjoying the Florida sunshine while exploring the scenic pathways that wind through this welcoming enclave.

The homes in Margaritaville are thoughtfully crafted to provide both comfort and style, offering a range of options to suit various tastes and preferences. From cozy cottages to spacious family homes, each residence is designed with modern amenities and a touch of tropical flair. The community is perfect for families, retirees, and anyone seeking a tranquil retreat in a vibrant setting.

Beyond the beautiful homes, Margaritaville boasts a wealth of community features that enhance the living experience. Residents can enjoy access to resort-style amenities, including sparkling pools, fitness centers, and lush green spaces that are perfect for picnics and outdoor activities. The community is conveniently located near shopping, dining, and entertainment options, ensuring that everything you need is just a stone’s throw away.

Whether you're looking to buy your first home, retire in paradise, or simply enjoy a vacation lifestyle year-round, Margaritaville in Rolling Oaks is the ideal destination. Come discover the charm and warmth of this delightful community, where every day feels like a getaway!

Newest Margaritaville, Rolling Oaks Homes with Sidewalks Community Features

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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