Rolling Oaks Ph 5 Single Family Homes For Sale in Kissimmee - 8 homes

Remarks: Kick back and embrace the laid-back island rhythm at this breezy lakefront retreat in Margaritaville Resort Orlando, perfectly positioned on Parrot Head Place. Wrapped in carefree Key West charm, this home delivers sun-splashed interiors, coastal hues, and a relaxed, barefoot-friendly layout that makes every day feel like vacation. Out back, your private pool and spa overlook tranquil water views, creating the ultimate setting for lazy mornings, afternoon floats, and sunset cocktails with a soundtrack of good vibes (NEW POOL HEATER FEB 2026). The open living spaces flow effortlessly for easy entertaining, while spacious bedrooms provide a calm, salt-air escape after long days of fun and sun. Perfectly located just minutes from Walt Disney World, Universal Orlando Resort, including the highly anticipated Universal Epic Universe, and SeaWorld Orlando, this home offers the best of both worlds—action-packed adventures by day and laid-back island living by night. Whether you’re chasing thrills, fireworks, or unforgettable family memories, you’ll love coming home to your own private oasis where the pace slows, the music softens, and relaxation takes center stage. Designed for both personal enjoyment and short-term rental success, this home captures the essence of island living with a splash of luxury. Just steps from resort amenities, dining, and entertainment, it’s a place where worries drift away, flip-flops are the dress code, and life moves at a perfectly unhurried pace. Multiple tropical pools with cabanas, lounging areas, and full food & beverage service. Island-inspired restaurants, poolside bars, and casual spots all within walking distance. The St. Somewhere Spa offers massages, facials, body treatments, and salon services. Find your latitude, adjust your attitude, and come home to a true five-o’clock-somewhere lifestyle—complete with lake views, poolside living, and pure Margaritaville Magic! Sale is contingent upon Buyer entering into a property management agreement with Vstays Property Management and assuming and honoring all existing future reservations/bookings.

Listing is courtesy of: FLORIDA IN MOTION REALTY INC (407-947-2757)

Listing Agent: Susan Koptieff (407-334-7770)

Remarks: A Margaritaville Resort beauty and fully furnished with the Ethan Allen Furniture Package. This 2-bedroom, 2.5-bath home is in the highly sought after Margaritaville Resort Orlando. It is the perfect blend of luxury, comfort, and unforgettable full-time or vacation living. Inside you'll find an inviting open-concept floor plan with upgrades throughout, including wood-look ceramic tile flooring, over- and under-cabinet lighting, and custom backsplash and island kickplate tiling in the kitchen. The open living area has in-ceiling speakers, a Klipsch soundbar, Samsung Frame TV, and a queen sleeper sofa for extra guests. Each of the two spacious bedrooms has a large flat screen TV and its own private ensuite bathroom, providing comfort and privacy for owners and guests alike.  The primary suite has a walk-in closet and its own balcony for morning views and coffee, and the second bedroom also has its very own balcony as well, making it the perfect place to unwind while enjoying breathtaking views. Your back patio is designed for ultimate outdoor living. You can enjoy the tranquil park views or relax in your very own hot tub. Your patio area is ideal for entertaining or relaxing after a day at work or the fun day at the parks with a patio table, chairs and sun loungers, giving you endless possibilities to create your own private oasis.  Whether you’re looking for a luxury vacation home, investment property, or a personal retreat, this rare offering delivers the best resort-style living just minutes from world-class attractions, dining, and entertainment. Sunset Walk is located within the resort and is filled with restaurants, a movie theater, live entertainment, and more. The resort also has H20 Waterpark and a ton of retail which is ALL walkable from this home. HOA and The Fins Up Club cover daily trash removal, internet, cable, phone, pest control, landscaping, free resort shuttle, shuttle to parks, resort pools, and fitness center.

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

Listing Agent: Nikki Felix (916-765-9564)

Remarks: It’s 5 O’clock right here in the world-renowned Margaritaville Resort Orlando! This spectacular, carpet-free home features durable tile flooring and ceiling fans throughout. It is a 1 story, 1 bedroom and 1 bath fully furnished cottage, beautifully themed and decorated. The kitchen opens seamlessly to the main living area, making it perfect for entertaining or vacation hosting. Enjoy the resort lifestyle being just steps from the resort amenities. Located in a pet-friendly community, which also has great dog park. The monthly HOA covers high-speed internet, cable, phone, daily doorstep garbage pickup, professional landscaping, and pest control. The Fins UP Beach Club gives you access to enjoy full access to world-class resort amenities including 7 resort pools, a fitness center/gym, an internal resort shuttle, and free transportation shuttles directly to the local theme parks. This unique resort setup is highly walkable, situated just steps from Island H2O Water Park and Sunset Walk’s vibrant mix of restaurants, bars, live music, Target, Ulta and more. Centrally located with lightning-fast access to Disney, Universal, SeaWorld, and Gatorland, this property is a premier choice for a primary residence, second home, or lucrative vacation investment.

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

Listing Agent: Nikki Felix (916-765-9564)

Remarks: Rare opportunity to own one of the few 1-bedroom cottages in Margaritaville Resort Orlando, ideally located in the highly sought-after FIRST phase, offering the closest walking distance to the resort’s pool, fitness center, and entertainment. This island-inspired retreat is filled with natural light, charm, and unbeatable convenience, placing you right in the heart of it all just minutes from Disney. Known as “A Twist of Lime,” this beautifully designed cottage welcomes you with a peaceful front porch perfect for morning coffee or evening relaxation. Inside, soaring 20-foot ceilings, dormer windows, and an abundance of natural light create an open and airy feel rarely found in a 1-bedroom home. The open-concept kitchen features wood cabinetry, stone countertops, and a layout ideal for entertaining or simply enjoying everyday living. The spacious primary suite includes a king-sized bedroom, full bath with walk-in shower, and direct access to the private rear brick-paver patio. This quiet outdoor space provides the relaxation needed to enjoy the Florida sunshine. A full-size washer and dryer add convenience and functionality. Located within one of Central Florida’s most unique resort communities, owners enjoy access to incredible amenities including multiple pools, restaurants, shopping, entertainment, walking paths, and a vibrant tropical atmosphere throughout the community. Whether you are looking for a vacation escape, second home, or investment opportunity, this rare cottage stands out with its unique layout, original phase location, and inviting coastal-inspired design. Short-term rentals are allowed, and future bookings may convey to the buyer if the current property management company is retained, offering added flexibility and potential income from day one.

Listing is courtesy of: XCELLENCE (866-595-6025)

Listing Agent: Dan Dinozzi (203-982-7164)

Remarks: BRAND NEW AC with 10 YEAR TRANSFERABLE WARRANTY! 5.99 INTEREST RATE for qualified buyers who use our preferred lender! PHASE 1 WATERFRONT 4 bedroom cottage in the heart of Margaritaville Resort located just 5 minutes from Disney! Just steps from the resort amenity area, this immaculately kept cottage is fully equip with Margaritaville Resort approved furnishings by Ethan Allen. This spacious open floorplan home has 4 bedrooms, all with their own en suite bathrooms and separate thermostats for each level, along with high end wood look tile, quartz countertops, wooden stairs, private owners closet, high ceilings, multiple private balconies, an outdoor shower, and so much more! The large fenced in patio features a private, heated pool, ample eating and entertaining space, and sweeping lagoon views. This property can be used as a full time residence, second home, or short term rental property. This resort style community features two large swimming pools, 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 Low maintenance resort living includes fully maintained grounds, home exterior, lawn care, and 24/7 roaming security.

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

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

Remarks: Short Sale. Welcome to “Bikinis & Martinis,” a unique and beautifully maintained cottage in the highly sought-after Margaritaville Resort Orlando, ideally located just steps from premier resort amenities. This 2-bedroom, 2.5-bathroom, two-story home offers a spacious and functional floor plan, making it perfect as a primary residence, second home, or vacation rental investment. Designed with inviting coastal architecture and filled with natural light, the home features an open-concept living and dining area with modern finishes throughout. The well-appointed kitchen includes quartz countertops, stainless steel appliances, abundant cabinetry, and a breakfast bar with seating—ideal for entertaining or everyday living. A large-capacity washer and dryer, ceiling fans, and thoughtful upgrades further enhance comfort and convenience. Step outside from the kitchen to your private tropical oasis, complete with a patio, lounge chairs, hot tub, lush landscaping, palm trees, and charming shell pathways—perfect for relaxing or hosting guests. Upstairs, both bedrooms offer privacy and feature en-suite bathrooms with glass-enclosed shower stalls. This home includes the Margaritaville Resort Orlando-approved “Sail Away” Ethan Allen furniture and housewares package, valued at over $25,000. Everything conveys with the sale, including blinds, drapes, TVs, artwork, kitchen essentials, dishware, linens, and more—making this property truly turnkey. Located within one of Central Florida’s most desirable resort communities, residents and guests enjoy world-class amenities, including multiple resort-style pools, a fitness center, spa services, and an on-site water park. Just a short walk away is the vibrant Sunset Walk entertainment district, featuring popular restaurants, bars, live music, retail, and family-friendly attractions. Conveniently located just minutes from Walt Disney World Resort, as well as Universal Orlando and SeaWorld, this property offers unmatched access to the best of Central Florida. Shopping, dining, and major travel routes—including Orlando International Airport—are all within easy reach. Whether you’re seeking a full-time residence, vacation getaway, or income-producing property, this exceptional cottage offers the perfect blend of location, lifestyle, and investment potential—where every day feels like a vacation.

Listing is courtesy of: CREEGAN GROUP (407-622-1111)

Listing Agent: Chris Creegan (407-622-1111)

Remarks: **7 Bedrooms | 8.5 Bathrooms | Waterfront Living at Its Finest** ENJOY DISNEY MAGIC KINGDOM AND EPCOT FIREWORKS FROM THE TOP DECK. Welcome to your dream home on the lake! This stunning 7-bedroom, 8.5-bathroom house just hit the market and it's everything you've been looking for. Sitting right on the water, you'll enjoy gorgeous sunsets from your backyard every single evening. No hauling suitcases up the stairs here — this home comes with its own elevator! Three balconies give you plenty of outdoor space to relax, and one of the balconies even has a TV and overlooks the lake. Talk about the perfect spot to unwind. Inside, you'll find beautiful tile flooring throughout, quartz countertops, solid wood cabinets, and stainless steel appliances in the kitchen. Every bedroom is generously sized with a private bath, giving everyone plenty of room to spread out. The large game room with a wet bar with a pool table is ideal for entertaining guests. Step outside to your private pool and spa, where lakefront views make every swim feel like a vacation. The sunsets from this property are truly something special. Location is a huge bonus here. You're just minutes from Walt Disney World, Island H2O Waterpark, Sunset Walk, and plenty of shopping — including Target Grocery just down the road on Rolling Oaks Boulevard. Here's the best part — live here full-time as your forever home or rent it out on Airbnb for excellent rental income. Either way, this lakefront gem is a smart investment you don't want to miss!

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

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

Remarks: Welcome to 8056 Dreamsicle Drive in Kissimmee, a beautifully maintained 2 bedroom, 2 1/2 bathroom home located in the highly sought-after Margaritaville Resort Orlando community. This charming two-story home features inviting coastal architecture, bright interior spaces, and a functional layout designed for both comfortable living and successful vacation rental potential. The exterior showcases a picturesque front porch and balcony along with tropical landscaping that complements the vibrant resort-style surroundings. Inside, the home offers an open-concept living area filled with natural light, tile flooring throughout the main living spaces, and modern finishes. The spacious kitchen features quartz countertops, stainless steel appliances, abundant cabinetry, and a convenient breakfast bar perfect for entertaining or casual dining. The adjoining living and dining areas create a welcoming space to relax or host guests. Each of the three bedrooms provides comfort and privacy, while the three full bathrooms provide updated fixtures and ample space for residents and visitors alike. The rear of the home features a private patio area ideal for outdoor seating, relaxation, or enjoying Florida’s warm weather. Located within the world-renowned Margaritaville Resort Orlando, residents and guests enjoy access to exceptional resort-style amenities including multiple swimming pools, a fitness center, spa services, water park access, and beautifully maintained walking paths. Just a short stroll away is the vibrant Sunset Walk entertainment district offering a variety of restaurants, live music venues, boutique shopping, and family-friendly attractions. Popular dining options nearby include Ford’s Garage, Estefan Kitchen, Rock & Brews, and multiple casual waterfront-style eateries perfect for enjoying the Florida lifestyle. This property offers an unbeatable location just minutes from Walt Disney World Resort, including Magic Kingdom, EPCOT, Hollywood Studios, and Animal Kingdom. Other major attractions such as Universal Orlando Resort, SeaWorld Orlando, and ICON Park are also easily accessible. For shopping enthusiasts, nearby options include Orlando Vineland Premium Outlets, The Mall at Millenia, and a wide variety of retail stores along US-192 and nearby ChampionsGate. Travel convenience is another advantage, with Orlando International Airport approximately 30 minutes away and Orlando Sanford International Airport about 50 minutes away, making travel simple for both homeowners and visiting guests. The home is also located near several medical facilities including AdventHealth Celebration Hospital, Orlando Health Horizon West Hospital, and HCA Florida Osceola Hospital, providing excellent healthcare access. With its prime location near world-class attractions, resort amenities, entertainment, dining, shopping, and major travel routes, 8056 Dreamsicle Drive offers an exceptional opportunity whether you are seeking a vacation home, investment property, or primary residence in one of Central Florida’s most desirable resort communities.

Listing is courtesy of: LIVE MVRK LLC (407-756-4563)

Listing Agent: Gabriel Flete (407-341-9663)