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

Welcome to Margaritaville, Rolling Oaks – an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This vibrant community offers a unique blend of relaxation and adventure, perfect for those seeking a tranquil escape while remaining close to the excitement of Orlando’s attractions.

Margaritaville, Rolling Oaks is a gated community that prioritizes your peace of mind with its secure, no-guard access. Here, you’ll discover beautifully designed homes that embody the spirit of coastal living, featuring open floor plans, modern amenities, and inviting outdoor spaces. Each residence is crafted with attention to detail and offers a perfect retreat after a day of exploring the nearby theme parks or enjoying the Florida sunshine.

The community itself is brimming with delightful features. Residents can enjoy access to a variety of amenities, including sparkling swimming pools, lush walking trails, and vibrant social spaces that foster a sense of camaraderie among neighbors. Whether you’re looking to unwind at the community clubhouse or take a leisurely stroll through the scenic surroundings, Margaritaville, Rolling Oaks has something for everyone.

Location is key, and this charming subdivision places you just minutes away from world-class attractions, shopping, and dining. Experience the best of both worlds – the serenity of a gated community and the thrill of Kissimmee’s vibrant lifestyle. Discover your dream home in Margaritaville, 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

Start Your Search