Margaritaville, Rolling Oaks Homes with Dog Park Community Features

Margaritaville, Rolling Oaks Homes with Dog Park Community Features

Welcome to Margaritaville at Rolling Oaks, an enchanting subdivision nestled in the heart of Kissimmee, Florida, within the vibrant Osceola County. This community is not just a place to live; it’s a lifestyle that embodies relaxation, fun, and a touch of paradise. With its tropical-inspired architecture and lush landscaping, Margaritaville offers a unique blend of resort-style living and the comforts of home.

Each residence in Rolling Oaks has been thoughtfully designed to maximize comfort and style, featuring open floor plans, modern amenities, and spacious outdoor areas perfect for entertaining or simply unwinding. Whether you’re seeking a cozy retreat or a spacious family home, there’s something for everyone in this delightful community.

One of the standout features of Margaritaville is its commitment to pet-friendly living. With a dedicated dog park, furry residents can enjoy their own space to romp and play, making it a perfect place for dog lovers. Imagine taking leisurely strolls with your pup along the scenic pathways, or watching them frolic with friends in the park. This community truly caters to the needs of every family member, including your four-legged companions.

Beyond the homes and the dog park, Margaritaville at Rolling Oaks offers a wealth of amenities designed to foster a sense of community and connection. From sparkling pools to social gathering spaces, residents can enjoy a vibrant lifestyle filled with activities and events.

Discover the charm of Margaritaville at Rolling Oaks, where every day feels like a vacation, and your dream home awaits!

Newest Margaritaville, Rolling Oaks Homes with Dog Park 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
$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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