Rolling Oaks Ph 5 Single Family Homes For Sale in Kissimmee - 6 homes

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: Welcome to this one-of-a-kind, fully furnished with unique coastal decor, 3-bedroom, 3.5-bath home 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 featuring a beautiful kitchen with an upgraded tile flooring and cabinets and a custom backsplash, seamlessly flowing into the dining and living areas with a 75" in TV or enjoy the tranquil park views and no rear neighbors on your 22x22 oversized patio. Ideal for entertaining or relaxing after a day at the parks. Each of the three spacious bedrooms have large flat screen TVs and their private ensuite bathrooms, providing comfort and privacy for owners and guests alike. The primary suite is truly exceptional, boasting 14ft vaulted ceilings, an oversized bathroom, dual walk-in closets, and exclusive access to a wraparound third-story balcony—the perfect place to unwind while enjoying breathtaking views, including nightly Disney fireworks. The oversized back patio really sets this home apart—the largest of its kind in Margaritaville. Designed for ultimate outdoor living, it is already equipped with electrical for a future hot tub and a retractable awning, giving you endless possibilities to create your own private oasis. Whether you’re looking for a luxury vacation home, investment property, or personal retreat, this rare offering delivers the best of resort-style living just minutes from world-class attractions, dining, and entertainment. Sunset Walk is filled with restaurants, a movie theater and live entertainment. 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 trash, internet, cable, phone, pest control, landscaping, pools and the gym.

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

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

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: 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)

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!

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

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

Remarks: Under contract-accepting backup offers. MARGARITAVILLE RESORT ORLANDO COTTAGE FOR SALE! This Two Story Home Features 3 Bedrooms and 3 Bathrooms with Additional Bonus Room with Built In Twin Bed. Gorgeous Backyard with Paved Patio with a HOT TUB Overlooking Huge Grass Area with Tiki Huts and Tropical Foliage. Primary Bedroom on First Floor with En-Suite Bathroom and French Doors that Open to Patio. The Kitchen Features Upgraded Stainless Steel Appliances and Quartz Countertops!. This Home also Features 'WOOD" Tile Flooring, Ceiling Fans Throughout, High Capacity Washer and Dryer and Abundant Natural Light. Furniture/Housewares Package is INCLUDED in List Price! Also Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Utensils, Dishware, Linens, and so MUCH MORE! This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! This Unique First Of Its Kind Resort Has Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail And More! LOCATED MINUTES FROM DISNEY PARKS!, All While Being Conveniently Close To The Best Shopping, Dining, And Entertainment Options In Florida. This Home Offers More Than Just A Place To Stay - it's A Lifestyle Of Resort-Style Living, Where Everyday Feels Like A Vacation.

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

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