Margaritaville, Rolling Oaks Homes with Stucco Exterior Construction

Welcome to Margaritaville at Rolling Oaks, a vibrant community nestled in the heart of Kissimmee, Florida, within the picturesque Osceola County. This unique subdivision offers an enchanting blend of tropical charm and modern convenience, making it the perfect destination for those seeking a laid-back lifestyle infused with a touch of paradise.

Margaritaville at Rolling Oaks is designed to capture the essence of island living, featuring stunning homes with beautiful stucco exterior construction that not only enhance curb appeal but also provide durability and low maintenance. Each residence is thoughtfully crafted to reflect a relaxed, coastal aesthetic, with spacious layouts that invite natural light and create an inviting atmosphere for family gatherings and entertaining friends.

The community is strategically located just minutes away from world-renowned attractions such as Walt Disney World and Universal Studios, making it an ideal choice for both full-time residents and vacation homeowners. Enjoy the convenience of nearby shopping, dining, and recreational options, all while basking in the serenity of your own private retreat.

Residents of Margaritaville at Rolling Oaks also have access to a plethora of amenities, including resort-style pools, fitness centers, and lush green spaces, ensuring that every day feels like a vacation. Whether you’re sipping cocktails by the pool or taking a leisurely stroll through the beautifully landscaped grounds, this community promises a lifestyle that is relaxing, vibrant, and full of sunshine.

Discover your dream home in Margaritaville at Rolling Oaks, where the spirit of island living awaits you!

Newest Margaritaville, Rolling Oaks Homes with Stucco Exterior Construction

$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

$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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