Margaritaville, Rolling Oaks Homes with Two Story Property Description

Welcome to Margaritaville in Rolling Oaks, a vibrant subdivision nestled in the heart of Kissimmee, Florida. This enchanting community is a true paradise for those seeking a blend of relaxation and adventure. With its tropical-inspired ambiance, Margaritaville offers residents a unique lifestyle that captures the essence of the Sunshine State.

The homes in this delightful neighborhood are designed with modern living in mind, featuring stunning two-story properties that exude charm and sophistication. These spacious homes boast open floor plans, allowing for seamless flow between living spaces, perfect for both entertaining and everyday living. Large windows invite abundant natural light, creating a warm and inviting atmosphere throughout.

Each two-story home is equipped with state-of-the-art amenities and stylish finishes, from gourmet kitchens to luxurious master suites. Many properties also offer outdoor living spaces, ideal for enjoying Florida’s year-round sunshine. Imagine sipping your morning coffee on a private balcony or hosting barbecues in your beautifully landscaped backyard.

Margaritaville in Rolling Oaks is more than just a community; it’s a lifestyle. Residents enjoy access to a variety of amenities, including resort-style pools, fitness centers, and walking trails. The vibrant social scene encourages neighbors to connect and build friendships, making it easy to feel at home.

Located conveniently near shopping, dining, and entertainment options, Margaritaville is perfectly positioned for those who crave both relaxation and adventure. Whether you’re seeking a permanent residence or a vacation getaway, this charming subdivision offers the ideal blend of comfort and leisure. Come discover your slice of paradise in Margaritaville!

Newest Margaritaville, Rolling Oaks Homes with Two Story Property Description

$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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