Margaritaville, Rolling Oaks Homes with HOA Yes/No

Margaritaville, Rolling Oaks Homes with HOA Yes/No

Welcome to Margaritaville in Rolling Oaks, a captivating subdivision nestled in the heart of Kissimmee, Florida. This vibrant community is a true oasis for those seeking a blend of relaxation and adventure, perfectly situated in the picturesque Osceola County. With its tropical-inspired design and laid-back atmosphere, Margaritaville is more than just a neighborhood; it’s a lifestyle.

The homes in this charming subdivision are thoughtfully designed, offering a variety of floor plans that cater to diverse tastes and needs. Whether you’re looking for a cozy two-bedroom retreat or a spacious family home, Margaritaville has something for everyone. Each residence boasts modern amenities, stylish finishes, and private outdoor spaces that invite you to enjoy the beautiful Florida sunshine.

As a resident of Margaritaville, you’ll enjoy access to a range of community features that elevate your living experience. The homeowners association (HOA) ensures that the neighborhood is well-maintained, enhancing the overall appeal and value of your home. The HOA also organizes community events and activities, fostering a strong sense of camaraderie among neighbors.

Location is key, and Margaritaville doesn’t disappoint. You’ll find yourself just minutes away from world-renowned attractions, shopping, and dining options, making it easy to enjoy everything Kissimmee has to offer. Whether you’re looking to invest in a vacation home or a permanent residence, Margaritaville in Rolling Oaks is a delightful choice that combines comfort, community, and convenience. Come and experience the magic of this enchanting subdivision today!

Newest Margaritaville, Rolling Oaks Homes with HOA Yes/No

$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
$575,000
4 Beds ⋅ 5 Baths ⋅ Margaritaville, Rolling Oaks SubDv. ⋅ 34747 Zip Code
BEST DEAL IN MARGARITAVILLE!!!! This world famous resort exudes cheer with a colorful palette of tropical hues and lush landscaping! Imagine owning a 3 story Island style home drenched in aqua blue with stylish awnings and crisp white balconies, this wins hands down for curb appeal!! Worth mentioning is the quality construction and choice of a concrete tile roof in lieu of shingles and a center of state location! The interior is fully furnished with superbly crafted Ethan Allen furniture guaranteed to last with solid wood construction and durable fabrics, a 55k package. All bedding & linens are from the Margaritaville Hotel, ensuring the same luxurious slumber! Everything is included from tv’s to modems to artwork and silverware! All appliances large and small also convey! Luxury vinyl plank keeps things cohesive and very low maintenance. This floor plan is spacious and gives plenty of privacy to large parties looking to kick back and relax! The backyard has a new hot tub and is a great spot to lounge and enjoy a cocktail or two, because it’s always 5 o’clock somewhere! Yes, it can get catchy…so don’t blow out your flip flop or step on a pop top rushing to see this amazing life you could be living or benefitting from! A cheeseburger in paradise is an understatement with an incredible array of restaurants and specialty shoppes throughout the resort. Sunset Walk offers an array of international delicacies. Dine and dance the night away at Estefan’s Kitchen enjoying decadent Cuban cuisine or pop into the Wharf for fresh seafood, a cold beer and live music! With countless choices and activities you’ll never run out of new experiences to try and savor. On site make a splash at the Island H20 water park, one of the many pools or jump on the free shuttle to the parks! A reservation is required thru Fins Up Beach Resort.

8045 Lost Shaker Lane, Kissimmee
Start Your Search