Margaritaville, Rolling Oaks Townhomes for Sale in Kissimmee - 10 townhouses

Remarks: Live the vacation lifestyle every day or capitalize on one of Central Florida’s strongest short-term rental markets. Welcome to 2968 Caribbean Soul Dr, a fully furnished, turn-key townhome in the world-famous Margaritaville Resort Orlando—just minutes from Disney. This updated 2-bedroom, 2.5-bath retreat with a bonus loft delivers the perfect blend of luxury, comfort, and income potential. Step inside to an airy open layout with designer finishes, ceramic tile throughout, a modern kitchen with pantry, and a private primary suite featuring a walk-in closet and spa-inspired bath. Every detail is crafted to give guests the resort experience they expect—making this home Airbnb & VRBO ready from day one. Outside your door, enjoy access to unmatched amenities: multiple lagoon-style pools, a full fitness center, world-class restaurants and bars, shopping, entertainment, trolley service, walking/biking trails, and 24/7 gated security. HOA includes exterior maintenance, cable, internet, and resort amenities for a true low-maintenance lifestyle. Whether you’re searching for a vacation home near Disney, a high-performing short-term rental investment, or a stylish low-maintenance residence, this property delivers it all. Back on the market and ready for immediate occupancy or rental activation. Come see why Margaritaville remains one of Orlando’s top resort communities. ? Zoned for short-term rentals—Airbnb & VRBO friendly ? Ideal for primary residence, vacation retreat, or investment property ? Move-in ready—just bring your suitcase! Schedule your private showing today!

Listing is courtesy of: KELLER WILLIAMS CLASSIC (407-292-5400)

Listing Agent: Codie Eldery (407-881-3882)

Remarks: Bright and spacious TWO BEDROOM VILLA WITH BONUS BUNK ROOM located in the heart of Margaritaville Resort just 5 minutes from Disney! This spacious townhome is located on a premium lot with open greenspace views and has two large bedrooms, plus a bonus bunk room, cozy and perfect for children or guests. It also comes with high end wood look tile, quartz countertops, upgraded appliances, wooden stairs, private owners' closet, high ceilings, and so much more! This property can be used as a full-time residence, second home, or short-term rental property. This resort style community features three large swimming pools near the Margaritaville Resort Hotel, 4 pools just steps from the villa itself, multiple restaurants and bars, fitness center, full-service spa, lush and tranquil walking trails to all ends of the community, as well as a moments walk to all of the restaurants, bars, shops and entertainment that Sunset Walk has to offer! Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming and manned gated security entrance.

Listing is courtesy of: COLDWELL BANKER REALTY (407-352-1040)

Listing Agent: Jenna Palmero (407-697-8727)

Remarks: Welcome to Paradise. Margaritaville Orlando 3 Bedroom 3 Bath Villa Turnkey Ready for your Personal Vacation Home or Short Term Rental investment property. The Villa showcases an MRO approved City Furniture/Housewares Package ($35K Included), ceiling fans, upgraded appliances, sleek QUARTZ countertops, and beautiful 'wood 'ceramic tile flooring. A high-capacity washer and dryer conveniently located on the second floor. Resort features multiple pools, a state-of-the-art gym, H2O on-site water park, Sunset Walk Restaurants, bars, live music, retail, and more! Terrific location just minutes from DISNEY with free shuttle to the Disney, Universal and Sea World Parks. Furniture/Housewares Package included in list price. Don't Delay !

Listing is courtesy of: LOKATION (954-545-5583)

Listing Agent: Brian Webber (407-399-1408)

Remarks: STUNNING FULLY FURNISHED COTTAGE FOR SALE AT MARGARITAVILLE RESORT ORLANDO with PRIVATE HEATED POOL AND SPA!. This Cottage has 4 Bedrooms, 4 Full Baths, Upgraded "Wood" Tile Flooring, Stainless Steel Appliances and Ceiling Fans Throughout. Kitchen has Large Counter Space, High End Granite Countertops and Windows with Lots of Natural Light. Primary Bedroom on the First Floor with En-Suite Bathroom, Separate Shower and Separate Tub. Three Additional Bedrooms with Access to a Large Balcony Overlooking the Pool. Living Area with Indoor/Outdoor Access to Backyard with a Paved Patio, HEATED POOL AND SPA. High Capacity Washer and Dryer. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES ALL Furniture and Housewares, Also Includes Blinds, Drapes, TVs, Artwork, Linens, and So MUCH MORE! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants Bars, Live Music, Retail, Live Music and More! LOCATED MINUTES FROM DISNEY! It's A Lifestyle Choice for Living or a Great Investment Property For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Suzanne Docobo (954-304-4932)

Remarks: Welcome to your ultimate getaway at 3049 Caribbean Soul Drive! This fully furnished, professionally decorated 4-bedroom, 3-bathroom townhome is the epitome of island living. As an end unit, you'll enjoy extra privacy and an abundance of natural light. Step outside and take in the serene water views, or simply walk a few steps to one of the community's beautiful pools. This property is perfect as a vacation home or an investment property, with its vibrant, Key West-style architecture and turnkey setup, complete with all the furniture, art, and decor you need to start enjoying the laid-back lifestyle immediately. Situated within the Margaritaville Orlando Resort, this townhome offers a lifestyle of luxury and convenience. Residents and guests have access to an impressive array of amenities, including multiple resort-style pools with a lazy river and water slide, the St. Somewhere Spa, a 24-hour fitness center, and a variety of on-site restaurants and bars like Euphoria Fish House and the Salty Rim Bar & Grill. The resort also features the Promenade at Sunset Walk, a vibrant destination for shopping, dining, and entertainment, and provides a complimentary shuttle service to Walt Disney World theme parks. This prime location places you close to Central Florida's world-famous attractions, premier dining, and top-tier shopping, making it a perfect retreat for both relaxation and adventure.

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: This fully FURNISHED 3 bedroom townhome in Margaritaville Resort Orlando offers one of the best opportunities to own in a DISNEY area resort that allows SHORT TERM RENTALS. Whether you are looking for a vacation home, an income producing investment, or a place to enjoy Orlando year round, this property checks every box. Located just minutes from Walt Disney World, Margaritaville Resort is one of the MOST SOUGHT AFTER VACATION COMMUNITIES in Central Florida. Owners benefit from high demand for short term rentals, professional property management options, and a RESORT LIFESTYLE that attracts guests year round.This home is completely turnkey and furnished, allowing the new owner to start renting immediately without the time and expense of furnishing or designing the property. Simply close and begin generating income or enjoying the home. One of the biggest advantages of this property is its PROXIMITY to Sunset Walk, just about a 5 minute walk away, where you will find restaurants, shopping, live entertainment, bars, arcades, and a grocery store.This WALKABLE lifestyle is one of the main reasons guests choose to stay in Margaritaville. Owners and guests also enjoy access to resort style amenities including pools, water park access nearby, fitness center, entertainment, and the unique Margaritaville lifestyle experience that makes this community stand out from other vacation rental areas.With its prime location near Disney, strong rental potential, walkability to entertainment, and fully furnished turnkey condition, this property represents an EXCEPTIONAL OPPORTUNITY to own in one of Orlando’s most popular resort communities.

Listing is courtesy of: P4L REALTY LLC (407-845-9189)

Listing Agent: Michelle Fernandez (407-724-5033)

Remarks: Escape to the ultimate "Island Time" lifestyle with this stunning, fully furnished 3-bedroom, 3-bathroom townhome at 2993 Caribbean Soul Drive! This property is a jewel within the highly sought-after Margaritaville Resort Orlando, offering a true turnkey vacation experience. Its location couldn't be better—you're mere steps away from one of the resort's beautiful community pools, inviting you to dive into paradise the moment you arrive. Owners and guests enjoy access to the resort's phenomenal amenities, including multiple lagoon pools, a relaxing lazy river, the full-service St. Somewhere Spa, the Fins Up Fitness Center, delicious dining options, lively bars, and the adjacent Promenade at Sunset Walk entertainment district. This townhome is a dream acquisition for both vacation home buyers and savvy investors. Beyond the resort, you are perfectly positioned to enjoy Central Florida's best, with Walt Disney World, world-class dining, premium shopping, and all the region's top attractions just minutes away. Secure your piece of paradise and a reliable income stream with this effortless, high-demand investment opportunity!

Listing is courtesy of: TEAM DONOVAN (407-705-2616)

Listing Agent: James Donovan (407-705-2616)

Remarks: Welcome to 3184 Caribbean Soul Dr, a stunning 4-bedroom, 3-bathroom townhouse in the vibrant Margaritaville Orlando community. This end unit offers privacy and convenience with the community pool just steps away from your door. The home features beautiful wood cabinets, stylish tile floors throughout, and modern stainless steel appliances. What makes this property truly special is that all furniture and decor stays with the home, making it completely move-in ready. This versatile property works perfectly as an Airbnb rental, full-time residence, or your personal vacation retreat. The location puts you close to exciting attractions like Island H2O water park, Sunset Walk's entertainment district, movie theaters, shopping centers, and diverse dining options. Nearby amenities include Formosa Winery Tasting House for wine enthusiasts, Target Grocery for convenient shopping,Walt Disney World. The property also offers easy access to public transportation. Whether you're looking for an investment opportunity or a place to call home in sunny Florida, this Margaritaville townhouse delivers comfort, style, and endless possibilities in one attractive package.

Listing is courtesy of: LUXE PROPERTIES LLC (305-809-7650)

Listing Agent: Deanna Meredith (407-331-6542)

Remarks: 2 BEDROOM 2 BATHROOM COTTAGE

Listing is courtesy of: FIRST STEP REALTY GROUP (786-641-6840)

Listing Agent: Kevin Velazquez (786-298-0394)

Remarks: Position your portfolio for success with this premier short-term rental opportunity at 8189 Surf Street in Margaritaville Resort Orlando. Located within one of Central Florida’s most recognized vacation rental destinations, this fully furnished 2-bedroom, 2.5-bath villa offers a true turnkey investment—professionally designed, impeccably maintained, and ready to generate immediate rental income. Thoughtfully designed to maximize guest appeal and occupancy, the villa features a bright open-concept floor plan, soaring ceilings, quartz countertops, upgraded appliances, and premium coastal finishes throughout. The private patio overlooking a tranquil pond creates an inviting outdoor retreat—an amenity highly valued by vacation guests seeking relaxation after a day at the parks. The home is delivered fully furnished with the upgraded Margaritaville Furniture Package, eliminating startup costs and ensuring seamless onboarding into the resort’s rental program. Owners and guests enjoy access to a full suite of resort-style amenities, including multiple pools, on-site restaurants, live entertainment, a fitness center, kids’ club, and the popular Fins Up Beach Club. The resort’s prime location—just minutes from Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando—drives consistent year-round tourism demand, while on-site attractions like Island H2O Live! Water Park further enhance guest experience and booking potential. Nearby, Promenade at Sunset Walk offers walkable dining, retail, and entertainment options that increase guest satisfaction and repeat stays. Backed by the strength of the Margaritaville brand and situated in one of the highest-performing vacation rental corridors in the country, this property represents a compelling opportunity for investors seeking strong occupancy, premium nightly rates, and long-term appreciation potential. Capitalize on a proven short-term rental model in a high-demand market—schedule your private showing today.

Listing is courtesy of: RE/MAX PRIME PROPERTIES (407-347-4512)

Listing Agent: Nick Whitehouse (407-902-4639)