Margaritaville, Rolling Oaks Homes with Sidewalk Exterior Features

Margaritaville, Rolling Oaks Homes with Sidewalk Exterior Features

Welcome to Margaritaville in Rolling Oaks, a vibrant subdivision nestled in the heart of Kissimmee, Florida. This enchanting community perfectly captures the essence of laid-back living with a touch of tropical flair. With its charming streets lined with beautifully designed homes, Margaritaville offers a unique blend of comfort and style, making it an ideal place to call home.

The subdivision features an array of homes that boast delightful exterior designs, complete with inviting sidewalks that encourage leisurely strolls and friendly conversations with neighbors. Imagine stepping out of your front door and taking a peaceful walk along the tree-lined paths, where you can soak in the warm Florida sunshine and enjoy the picturesque surroundings.

Each home in Margaritaville is thoughtfully crafted to provide a perfect blend of modern amenities and classic charm. With spacious layouts, contemporary finishes, and outdoor living spaces designed for relaxation and entertainment, these residences are perfect for families and retirees alike. The community is designed to foster a sense of camaraderie, offering residents the opportunity to connect and create lasting friendships.

Located in Osceola County, Margaritaville is just a stone's throw away from the excitement of Kissimmee, where you can explore a variety of dining, shopping, and entertainment options. Plus, with easy access to major highways, you're just minutes away from the world-famous attractions of Orlando.

Whether you're looking for a vacation home or a permanent residence, Margaritaville in Rolling Oaks is the perfect destination for those seeking a vibrant community and a relaxed lifestyle. Come discover your slice of paradise today!

Newest Margaritaville, Rolling Oaks Homes with Sidewalk Exterior Features

8201 Surf Street, Kissimmee
$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
2916 On The Rocks Point, 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
8045 Lost Shaker Lane, 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
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