Margaritaville, Rolling Oaks Homes with Two Story Property Description

Welcome to Margaritaville at Rolling Oaks, a vibrant and enchanting subdivision nestled in the heart of Kissimmee, Florida. This delightful community captures the essence of tropical living, combining laid-back charm with modern conveniences. Just a stone's throw away from the magical attractions of Orlando, Margaritaville offers the perfect blend of relaxation and adventure, making it an ideal destination for both homeowners and vacationers alike.

The homes in Margaritaville are designed with a captivating two-story layout that maximizes space and comfort. With a variety of floor plans to choose from, these residences feature open-concept living areas that are perfect for entertaining family and friends. Large windows flood the interiors with natural light, creating a warm and inviting atmosphere. Each home boasts stylish finishes and modern amenities, ensuring a luxurious lifestyle in a picturesque setting.

Step outside and you’ll find beautifully landscaped yards and charming outdoor spaces, perfect for enjoying Florida's year-round sunshine. Residents can take advantage of the community's resort-style amenities, including sparkling pools, fitness centers, and vibrant social areas that encourage a sense of community and connection.

Whether you’re looking for a primary residence or a vacation home, Margaritaville at Rolling Oaks offers an unparalleled lifestyle in Kissimmee. With its close proximity to world-renowned attractions, shopping, and dining, this subdivision is more than just a place to live; it’s a vibrant community where every day feels like a getaway. Discover your slice of paradise in Margaritaville today!

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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