Rolling Oaks Real Estate - Search all Rolling Oaks homes and townhouses for sale.

8 Beds ⋅ 9 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

'EASY BREEZY' Cottage on Margaritaville Resort Orlando's 'TROPHY ROW'! EXTREMELY RARE OPPORTUNITY TO OWN ONE of the LARGEST WATERFRONT COTTAGES WITH POOL and SPA Plus Your Very Own ELEVATOR ($40k Upgrade)! Home is FULLY HANDICAP ACCESSIBLE. 4131-A Model, 8 Bedrooms, 8 Full Bathrooms and 1 Half Bathroom with IN PARADISE Upgrade. This Amazing Home Features One En Suite Bedroom on First Floor Along with Another Bedroom with Hallway Bath, Large Kitchen with Tiled Backsplash and Breakfast Bar, Spacious Pantry with CUSTOM SHELVING, Living Room with Sliders that Lead to Beautiful Paved Patio, Fenced In Backyard has Covered Area, Cabana Bath, Outdoor Speakers and TV Hookup, In-Ground Pool and Spa with Custom Safety Handrails and Spectacular SUNSET VIEWS Over the Pond! Second Floor has Primary Suite with Separate Tub and Shower, CUSTOM BUILT CLOSET and Access to Balcony Overlooking Backyard. Three En Suite Bedrooms Complete Second Floor with Hallway Access to the Large Front Balcony. Third Floor has Upgraded Mosaic Tiled Alcoves which Compliment the Stairs leading to a Suite with Separate Tub and Shower, Access to Huge Tiled and COVERED PARTY DECK with Sweeping Lake Views. Loft with Wet Bar is Next to the Eighth Bedroom with Full Bathroom. Home also has Covered Front Porch, Upgraded 'Wood' Tile Flooring, Quartz Countertops. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Unique First of its Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! LOCATED MINUTES FROM DISNEY PARKS! There's Nothing Like Living the Margaritaville Lifestyle in Paradise!

3056 Parrot Head Place, Kissimmee

$1,349,000

8 Beds ⋅ 9 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

JUST REDUCED $50,000! NOW IS THE TIME! 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.

3052 Parrot Head Place, Kissimmee

$1,275,000

7 Beds ⋅ 9 Baths ⋅ Rolling Oaks Ph 5 SubDv. ⋅ 34747 Zip Code

**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!

8017 Surf Street, Kissimmee

$774,900

4 Beds ⋅ 4 Baths ⋅ Rolling Oaks Ph 6b SubDv. ⋅ 34747 Zip Code

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!

8014 Knee Deep Road, Kissimmee

$709,900

5 Beds ⋅ 6 Baths ⋅ Rolling Oaks Ph 6b SubDv. ⋅ 34747 Zip Code

Beautiful 5 bedrooms, 5 and a half bathroom POOL COTTAGE ON AN OVERSIZED CORNER LOT located in Margaritaville Resort! Just moments from Disney World, this turn key cottage comes fully furnished with Margativille approved City Furniture. This highly sought after two-story floor plan features numerous upgrades, such as the wood-plank tile flooring, NEW EXTERIOR REPAINT, stainless-steel appliances, and long lasting tile roof. All colors, furniture and decorations were thoughtfully picked to make the cottage look and feel like a light beach breeze. Pastel colors on the interior and southern exposure bring lots of natural light. In here, living it up is a dream. Two bedrooms downstairs and three bedrooms upstairs, including the spacious master suite. All three bedrooms on the second floor include an en-suite bath for added convenience. Both guest bedrooms lead out onto their own private balconies, and outdoor space is accessible from the master suite, providing ultimate relaxation. Additional half-bath is accessible from the lanai, where you also step out onto your FULLY FENCED YARD WITH PRIVATE POOL. Margaritaville Resort offers plenty of amenities and a fantastic location. Easy access to highways, shopping, restaurants and most importantly to Disney parks. The cottage can be rented out as an investment property or make it fabulous full time or vacation living.

8082 Knee Deep Road, Kissimmee

$675,000

4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 6b SubDv. ⋅ 34747 Zip Code

This beautifully located property is part of the highly desirable Margaritaville Resort Orlando, delivering a true resort-style lifestyle just minutes from Walt Disney World, shopping, dining, and entertainment. Enjoy a vibrant community surrounded by tropical landscaping, multiple pools, fitness amenities, and on-site restaurants, all designed for relaxed Florida living. Short-term rentals are permitted, making this an excellent option for personal use or income-producing potential. Convenient access to major highways provides easy travel to Orlando International Airport and Central Florida attractions. Experience island-inspired living where every day feels like a vacation. This property is being sold fully furnished.

8008 Sandy Toes Way, Kissimmee

$615,000

3 Beds ⋅ 2 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code

**Rare waterfront cottage in Margaritaville Resort Orlando!** One of the few cottages in the community with a premium direct waterfront location, this beautiful 3-bedroom, 2-bath home offers breathtaking water views from both private balconies and a lifestyle unlike any other. **Unlike heavily rented vacation homes, this residence has been privately enjoyed and carefully maintained**, giving it a like-new feel without the wear and tear often associated with short-term rental properties. Whether you're looking for a primary residence, vacation home, or investment property, this home is eligible for short-term rentals and can easily be placed into the resort's rental program if desired. Inside, you'll find numerous upgrades, including tile flooring throughout, an open-concept floor plan, a durable metal roof, quartz countertops, stainless steel appliances, and beautifully designed living spaces that are both stylish and functional. The thoughtfully selected coastal décor perfectly complements the home's character and inviting atmosphere. The spacious kitchen opens seamlessly to the living and dining areas, creating the perfect space for entertaining family and friends. One of the home's most desirable features is its two private waterfront balconies—one on each level—where you can enjoy peaceful water views, your morning coffee, or spectacular Florida sunsets. Margaritaville Resort Orlando offers an exceptional resort lifestyle with multiple resort pools, a fitness center, live entertainment, shopping, dining, Island H2O Water Park, and the vibrant Promenade at Sunset Walk featuring restaurants, bars, boutiques, and year-round entertainment. Located just minutes from Walt Disney World and Orlando's other world-famous attractions, this rare waterfront property offers an outstanding opportunity as a primary residence, second home, or income-producing investment.

8117 Surf Street, Kissimmee

$579,000

4 Beds ⋅ 5 Baths ⋅ Rolling Oaks Ph 6 SubDv. ⋅ 34747 Zip Code

CURRENTLY LEASED WITH GREAT TENANTS FOR $3,900 PER MONTH THROUGH 12/4/26! LEASE CAN BE ASSIGNED TO NEW BUYER! GORGEOUS 1990-A Model 3-Story Cottage For Sale at Margaritaville Resort Orlando with Convenient Central Resort Location! Home Features 4 Bedrooms and 4.5 Bathrooms. All Bedrooms Feature En-Suite Bathrooms. Kitchen has QUARTZ Countertops and Door Leading to Large Paved Patio with Shell Pathways, Palm Trees and Tropical Foliage. Home also Features Ceiling Fans, Upgraded Appliances, High Ceilings, 'WOOD' Tile Flooring Throughout, Built-in Closet Shelving, TANKLESS WATER HEATER, FULL SIZE W/D and Half Bathroom on First Floor. First Floor has Spacious Living Room Area and Kitchen. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! List Price INCLUDES Furniture/Housewares with Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishware, 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 Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation!

8044 Lost Shaker Lane, Kissimmee

$570,000

3 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 6b SubDv. ⋅ 34747 Zip Code

SELLER MOTIVATED - PRIVATE POOL: A must-see Cottage, Model 1384-A at Margaritaville Resort Orlando—bright, inviting, and designed for comfort, style, and tropical charm. This 3-bedroom, 3-bathroom home plus a versatile bonus room offers a smart layout and effortless livability. Step inside to find elegant wood-look tile floors that flow throughout, bathed in abundant natural light that highlights the contemporary finishes. The first-floor primary bedroom features an en-suite bath and French doors opening to a spacious backyard patio, creating a seamless indoor-outdoor living experience. The second floor hosts a second primary suite, a comfortable third bedroom, and a bonus room with a twin bed, plus a full third bathroom—ideal for families or guests needing flexible sleeping arrangements. A well-appointed kitchen awaits, offering modern appliances and convenient connectivity to the living areas, perfect for casual gatherings or entertaining. The backyard is a true standout, with a paved patio and lush tropical landscaping that creates a private oasis for relaxation and outdoor enjoyment. Additional highlights include an in-unit washer and dryer for everyday convenience and an overall design that blends resort-inspired appeal with practical comfort. This cottage is perfectly positioned to enjoy Margaritaville’s amenities and the vibrant resort lifestyle. Whether you’re seeking a stylish vacation hideaway or a solid rental opportunity, this adorable Cottage delivers curb appeal, comfort, and everyday ease in one attractive package. Call today for your private showing.

2946 Salted Rim Road, Kissimmee

$569,000

4 Beds ⋅ 5 Baths ⋅ Rolling Oaks Ph 6 SubDv. ⋅ 34747 Zip Code

Welcome to 2998 Salted Rim Road, where luxury, lifestyle, and investment opportunity come together in the heart of Margaritaville Resort Orlando! This fully furnished 4-bedroom, 4.5-bathroom vacation home offers 1,948 square feet of beautifully designed living space, with every bedroom featuring its own private en-suite bath for the ultimate guest experience. Ready to enjoy or generate income from day one, this turnkey home includes the Margaritaville-approved Island Breeze furniture package and is just minutes from Walt Disney World. Owners and guests enjoy world-class amenities, including resort-style pools, a water park, restaurants, shopping, and live entertainment. Whether you're searching for a high-performing vacation rental, a second home, or your next investment, 2998 Salted Rim Road is your chance to own a piece of paradise in one of Orlando's most sought-after resort communities.

2998 Salted Rim Road, Kissimmee

Rolling Oaks Homes for Sale

Rolling Oaks Homes For Sale