Margaritaville, Rolling Oaks Homes with Two Story Property Description

Welcome to Margaritaville at Rolling Oaks, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida. This tropical oasis is perfectly situated in Osceola County, offering residents a delightful blend of relaxation and recreation. With its laid-back atmosphere and charming architecture, Margaritaville is designed for those who seek a slice of paradise right at home.

The homes in this enchanting community feature stunning two-story designs that are both spacious and stylish. Each residence is thoughtfully crafted to provide an open and airy living space, with ample natural light flooding through large windows. The two-story layout offers the perfect balance of privacy and togetherness, making it ideal for families, couples, or anyone looking to enjoy a serene lifestyle.

Step inside these beautifully designed homes, and you’ll find modern kitchens equipped with sleek appliances, inviting living areas perfect for entertaining, and cozy bedrooms that promise restful nights. Many of these homes also boast outdoor patios or balconies, where you can soak in the warm Florida sun and enjoy the lush surroundings.

Margaritaville at Rolling Oaks is more than just a place to live; it’s a lifestyle. Residents can take advantage of the community’s fantastic amenities, including resort-style pools, fitness centers, and scenic walking trails. Plus, with nearby attractions like Disney World and Universal Studios, adventure is just around the corner.

Experience the charm of Margaritaville at Rolling Oaks—where your dream home awaits in the sunny embrace of Kissimmee!

Newest Margaritaville, Rolling Oaks Homes with Two Story Property Description

$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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