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

Welcome to Margaritaville in Rolling Oaks, a tranquil paradise nestled in the heart of Kissimmee, Florida. This charming subdivision offers a unique blend of relaxation and vibrant community living, making it the perfect destination for those seeking a slice of Florida’s sunshine.

Margaritaville is a gated community that boasts an array of beautifully designed homes, each exuding a sense of warmth and comfort. With no guard at the gate, residents enjoy the ease of access while still relishing the privacy and security that a gated community provides. The homes here are thoughtfully crafted, featuring modern amenities and open floor plans that cater to today’s lifestyle. Whether you're looking for a cozy retreat or a spacious family home, you’ll find a variety of options that suit your needs.

The community is surrounded by lush landscaping and serene waterways, creating an inviting atmosphere for outdoor enthusiasts. Residents can take advantage of the well-maintained walking trails, perfect for morning strolls or evening jogs, all while soaking in the stunning Florida sunsets.

Margaritaville in Rolling Oaks is not just a place to live; it’s a lifestyle. Enjoy the close-knit community feel while being just a stone's throw away from the excitement of Kissimmee. With nearby shopping, dining, and entertainment options, you’ll never run out of things to do.

Experience the charm of Margaritaville in Rolling Oaks—where every day feels like a vacation! Don’t miss your chance to be part of this vibrant community in beautiful Osceola County.

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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