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

Welcome to Margaritaville in Rolling Oaks, a vibrant and inviting subdivision nestled in the heart of Kissimmee, Florida, within the charming Osceola County. This delightful community captures the essence of laid-back living, where the spirit of island life meets modern comfort.

Margaritaville offers a unique blend of homes designed for relaxation and enjoyment, perfect for families, retirees, or anyone looking to embrace the Florida lifestyle. Each residence boasts an open-concept layout, featuring spacious living areas, gourmet kitchens, and luxurious outdoor spaces ideal for entertaining or unwinding after a long day. With a variety of home styles available, there’s something to suit every taste and preference.

One of the standout features of Margaritaville is its gated community status, providing residents with an added layer of privacy and security. While there is no guard on duty, the well-maintained entryways and serene surroundings create a welcoming atmosphere for all. Enjoy leisurely strolls through beautifully landscaped paths or take advantage of the community amenities designed to enhance your living experience.

Located just minutes away from world-renowned attractions, shopping, and dining, Margaritaville in Rolling Oaks offers the perfect balance of tranquility and accessibility. Whether you’re looking to invest in a vacation home or seeking a permanent residence, this community is the ideal backdrop for creating lasting memories. Embrace the charm and vibrancy of Margaritaville—your slice of paradise awaits!

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

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