Rolling Oaks Homes & Townhouses for Sale

Rolling Oaks Homes & Townhouses for Sale

8045 Surf Street, Kissimmee
$975,000
5 Beds ⋅ 6 Baths ⋅ S5159643 MLS
EXTREMELY RARE OPPORTUNITY! Own a stunning 5-BEDROOM, 6-BATH WATERFRONT COTTAGE WITH A PRIVATE POOL AND SPA in Margaritaville Resort Orlando for UNDER $1 MILLION! This BEAUTIFUL, FULLY FURNISHED cottage has an open-concept design that flows seamlessly into your own private backyard paradise, featuring a sparkling pool, relaxing spa, and BREATHTAKING WATER AND SUNSET VIEWS! Every bedroom features its own ensuite bathroom, plus there's a convenient pool bath to keep wet feet out of the house! Two bedrooms have private balconies overlooking the fenced pool area and tranquil water views, including a second-floor bedroom and the third-floor primary suite. The upstairs loft provides even more space for entertaining, whether it's GAME NIGHT, movie night, or even a silent disco with friends! Looking for a full-time residence, vacation getaway, or income-producing investment property? This cottage offers incredible flexibility! This cottage is TURNKEY, complete with the approved furniture and housewares package, it's ready to enjoy or prepare for short-term rentals, subject to applicable requirements. And the LOCATION? It's hard to beat! Margaritaville Resort Orlando offers a vibrant resort lifestyle with walkable access to restaurants, shopping, entertainment, a movie theater, and a water park! HOA and Fins Up Club services and amenities include internal resort transportation, scheduled theme park shuttle service, daily trash pickup, landscaping, pest control, twice-weekly pool service, cable, internet, and phone service. Enjoy access to 7 POOLS, a hot tub, fitness center, and select on-property discounts, subject to membership and access requirements. WATERFRONT. PRIVATE POOL & SPA. FIVE ENSUITE BEDROOMS. PLUS A SEPERATE POOL BATHROOM. FULLY FURNISHED. UNDER $1 MILLION. Opportunities like this deserve a closer look. Schedule your private showing today!

8045 Surf Street, Kissimmee

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040

8036 Lost Shaker Lane, Kissimmee
$435,000
4 Beds ⋅ 3 Baths ⋅ O6440491 MLS
Welcome to paradise at Margaritaville Resort Orlando, where every day feels like a vacation! This colorful, fully furnished single family cottage brings together resort style living, comfort, flexibility, and an incredible location. Whether you are searching for a primary residence, second home, vacation escape, or income producing property, this home gives you the freedom to make it your own. The property is currently operating as an active vacation rental and is being sold completely turnkey with the resort approved furniture package, furnishings, décor, appliances, and furniture included. Simply bring your suitcase and start enjoying the Margaritaville lifestyle! The flexible floor plan offers three bedrooms plus an additional private flex room that can be used as a fourth sleeping space, home office, or bonus room. The first floor features a king bedroom with a full bathroom, making it perfect for guests or anyone who prefers convenient first floor accommodations. Upstairs you will find another queen bedroom, a full shared bathroom, and a smaller flex room currently set up with a single bed. A stylish barn door upgrade was added to provide privacy, giving this space even more versatility. The spacious king primary suite is also upstairs and features its own private ensuite bathroom. Step outside and enjoy one of this home's standout features. The private patio opens to a generously sized backyard area, offering more usable outdoor space than many cottages within the resort. It is a wonderful spot to relax, entertain, or simply enjoy the Florida sunshine. The fun continues beyond your front door! Owners and guests can enjoy access to world class resort amenities, including the Margaritaville Hotel and Fins Up Beach Club. Spend your days poolside, soak up the tropical atmosphere, and enjoy the resort lifestyle right outside your door. Even better, dining, entertainment, and shopping are conveniently walkable, giving you the freedom to park the car and enjoy everything this exciting destination has to offer. Fully furnished, completely turnkey, packed with personality, and located in the heart of Margaritaville Resort Orlando, this cottage is ready for its next chapter. Live here full time, escape for weekends, make it your Florida second home, or continue operating it as a vacation rental. Flexibility is key and the possibilities are endless!

8036 Lost Shaker Lane, Kissimmee

Listing courtesy of XCELLENCE. 866-595-6025

3117 Caribbean Soul Drive, Kissimmee
$369,000
3 Beds ⋅ 3 Baths ⋅ O6434576 MLS ⋅ 3117 BLDG.
CDD BOND IS PAID OFF SAVING THOUSANDS ON YOUR PROPERTY TAX BILL EVERY YEAR! AMAZING VILLA IN MARGARITAVILLE RESORT ORLANDO! CURRENTLY LEASED WITH QUALITY LONG TERM TENANT THROUGH 10/23/26. LEASE CAN BE ASSIGNED TO BUYER. This Villa has 3 Bedrooms, 3 Baths, High-End Quartz Countertops, Upgraded "Wood" Tile Flooring and Appliances, High Capacity Washer and Dryer. Kitchen has Island with Seating, Large Counter Space and Windows with Lots of Natural Light. The Door from the Kitchen Leads you to a Beautiful Patio with Lounge Chairs and Tropical Landscaping, Palm Trees and Tropical Foliage with a Serene WATER VIEWS. Primary Bedroom Located Upstairs has En Suite Bathroom. Furniture Package is INCLUDED in List Price! Furniture Package Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, 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 Is Not Just a Residence; It's A Lifestyle Choice for Those Who Want to Experience the Best of Florida Living, Where Every Day Feels Like a Vacation.

3117 Caribbean Soul Drive, Kissimmee

Listing courtesy of EXP REALTY LLC. 888-883-8509

8217 Surf Street, Kissimmee
$435,000
4 Beds ⋅ 3 Baths ⋅ O6434314 MLS ⋅ 8217 BLDG.
Welcome to 8217 Surf St, a beautifully furnished 4-bedroom, 3-full-bath corner townhome located in the highly sought-after Margaritaville Resort Orlando. This spacious two-story home offers an open-concept living and dining area filled with natural light, stylish wood-look tile flooring, and a modern kitchen featuring quartz countertops, stainless steel appliances, ample cabinetry, and everything needed for a fully equipped vacation rental. The flexible floor plan includes a queen bedroom and full bathroom downstairs, while upstairs features three additional bedrooms: a spacious king bedroom, a queen bedroom, and a bunk room with two twin beds. Offered completely turnkey, the property includes all appliances, furniture, TVs, décor, artwork, housewares, kitchen necessities, dishware, linens, and furnishings, allowing the next owner to begin enjoying or renting the property right away. Whether you're looking for an income-producing short-term rental, a second home, or your own Florida vacation retreat, this property offers incredible flexibility. Margaritaville Resort Orlando offers a true resort lifestyle with multiple pools, fitness amenities, Island H2O Water Park, and convenient access to the restaurants, shopping, entertainment, and live music at Sunset Walk. Best of all, you're just minutes from Walt Disney World and Orlando's world-famous attractions. With its desirable corner location, spacious 4-bedroom layout, and complete turnkey setup, 8217 Surf St is an exceptional opportunity to own in one of Central Florida's most unique vacation resort communities—where every day can feel like a vacation.

8217 Surf Street, Kissimmee

Listing courtesy of XCELLENCE. 866-595-6025

8036 Surf Street, Kissimmee
$470,000
4 Beds ⋅ 3 Baths ⋅ O6434257 MLS
BEST PARKVIEW BACKYARD IN THE ENTIRE RESORT WITH GRASS! NOTHING ELSE COMPARES! 'PIRATES IN PARROTDISE' Cottage at Margaritaville Resort Orlando! Spacious Model 1384-C with 3 Bedrooms, 3 Bathrooms and an ADDITIONAL BONUS BEDROOM, BACK PATIO RETRACTABLE AWNING and a HOT TUB! Premium Location Near the Pedestrian Bridge! Spacious Living Room has a HUGE 75-INCH TV. IMMACULATE CONDITION ~ WELL MAINTAINED HOME. This home has NEVER been an STR and has been used as a SECOND HOME and LONG-TERM RENTAL most recently. First Floor Bedroom has En-Suite Bathroom and French Doors Leading to Spacious Backyard Patio with a Gorgeous GRASSY Backyard and TIKI HUTS. Second Floor has Primary En-Suite Bedroom with Front Balcony Access. Bonus Room has been Converted to a Bunk Room. The Kitchen features Upgraded Appliances, and Quartz Countertops. This Home also features Tile Flooring, Ceiling Fans Throughout, Washer and Dryer, Landscaping has Beautiful Foliage! All Furniture, Linens, Housewares and Decor INCLUDED IN LIST PRICE! Includes HIGH END ETHAN ALLEN FURNISHINGS, 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 and More! This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! LOCATED MINUTES FROM DISNEY PARKS! Come Enjoy the Margaritaville Lifestyle in Paradise!

8036 Surf Street, Kissimmee

Listing courtesy of EXP REALTY LLC. 888-883-8509

8201 Surf Street, Kissimmee
$299,999
2 Beds ⋅ 3 Baths ⋅ S5155480 MLS ⋅ 8201 BLDG.
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

Listing courtesy of TEAM DONOVAN. 407-705-2616

8117 Surf Street, Kissimmee
$615,000
3 Beds ⋅ 2 Baths ⋅ O6421843 MLS
**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

Listing courtesy of FORTUNE INTERNATIONAL REALTY. 305-400-6393

3145 Caribbean Soul Drive, Kissimmee
$285,000
2 Beds ⋅ 3 Baths ⋅ O6413644 MLS ⋅ Na BLDG.
Short Sale. SHORT SALE – Welcome to this beautifully maintained 2-bedroom, 2.5-bath home located in the highly sought-after Margaritaville Resort Orlando community. Offered fully furnished, this property is ideal as a primary residence, second home, short-term vacation rental, or long-term investment property. This charming two-story home features inviting coastal-inspired architecture, bright and airy living spaces, and a functional floor plan designed for comfortable living and exceptional rental performance. The private rear patio provides the perfect space for outdoor dining, relaxation, and enjoying Florida’s year-round sunshine. One of Margaritaville Resort Orlando’s most desirable floor plans, this immaculately maintained home has a strong rental history and is located just minutes from Central Florida’s world-famous attractions. Residents and guests enjoy access to outstanding resort-style amenities, including multiple swimming pools, a fitness center, full-service spa, water park access, on-site restaurants and bars, and scenic walking trails throughout the community. The home is also within walking distance of Sunset Walk, a vibrant entertainment district featuring live music, boutique shopping, family-friendly attractions, and an impressive selection of restaurants and nightlife. Low-maintenance resort living includes exterior home maintenance, landscaping, lawn care, and 24/7 gated security with both staffed and roaming patrols. Ideally located just minutes from Walt Disney World Resort, including Magic Kingdom, EPCOT, Hollywood Studios, and Animal Kingdom, with easy access to Universal Orlando Resort, SeaWorld Orlando, and ICON Park. This is a rare opportunity to own a turnkey home in one of Orlando’s premier resort communities.

3145 Caribbean Soul Drive, Kissimmee

Listing courtesy of MORGAN PROPERTY SOLUTIONS INC. 407-982-7097

2968 Caribbean Soul Drive, Kissimmee
$294,000
2 Beds ⋅ 3 Baths ⋅ O6416435 MLS ⋅ 2968 BLDG.
Short Sale. TURNKEY and ready for move in or rent out ! Welcome to 2968 Caribbean Soul Drive in Margaritaville Resort Orlando, one of Central Florida's most sought-after vacation home and short-term rental communities. This fully furnished, turnkey 2-bedroom, 2.5-bath townhome with a versatile loft offers an exceptional opportunity for investors, vacation home buyers, and those seeking a low-maintenance Florida lifestyle. Zoned for short-term rentals and located just minutes from Walt Disney World, this property is perfectly positioned to capitalize on the thriving Orlando vacation rental market. Step inside to discover an open-concept floor plan featuring ceramic tile flooring, soaring ceilings, solid surface countertops, designer finishes, and a modern kitchen that flows seamlessly into the living and dining areas. Upstairs, the spacious primary suite offers a walk-in closet and private bath, while the additional bedroom and loft provide flexible accommodations for guests and families. What truly sets this property apart is its incredible income-producing potential. guests are drawn to Margaritaville's world-famous resort atmosphere and unbeatable location near Orlando's top attractions. The home is offered fully furnished, allowing for immediate occupancy or rental activation. Residents and guests enjoy access to resort-style amenities including multiple lagoon-style pools, fitness center, restaurants, bars, shopping, walking trails, entertainment venues, trolley service, and 24-hour gated security. HOA services include exterior maintenance, cable, internet, and community amenities, creating a truly hassle-free ownership experience. Located in the heart of Kissimmee's tourism corridor, this home places visitors within minutes of: Walt Disney World Resort Disney's Animal Kingdom EPCOT Disney Springs Universal Orlando Resort SeaWorld Orlando Margaritaville Promenade at Sunset Walk Island H2O Water Park ESPN Wide World of Sports Championship golf courses Shopping, dining, and entertainment throughout Central Florida Whether you are searching for a high-performing vacation rental, a Disney-area investment property, a second home, or a full-time residence, this exceptional Margaritaville Resort Orlando townhome offers location, lifestyle, and investment potential all in one.

2968 Caribbean Soul Drive, Kissimmee

Listing courtesy of KELLER WILLIAMS CLASSIC. 407-292-5400

3054 Pirate Way, Kissimmee
$299,999
1 Beds ⋅ 1 Baths ⋅ S5150421 MLS
Welcome to Pirate Way — EXTREMELY RARE OPPORTUNITY to own a 1 out of 7, 1-bedroom cottage located in the heart of Margaritaville Resort Orlando for under $300k! If you've been dreaming of owning your own piece of paradise, this charming, TURNKEY cottage offers the perfect combination of vacation-home lifestyle, resort living and investment potential. Step inside and you'll immediately feel the Margaritaville vibe. This FULLY FURNISHED, one-story cottage features ceiling fans throughout, a bright and colorful coastal-inspired design, and an open-concept kitchen that flows seamlessly into the living area — perfect for relaxing after a day at the parks or entertaining family and friends and NO carpet! Step outside to your private back patio, complete with a table and four chairs plus two lounge chairs — the perfect spot to enjoy your morning coffee or unwind after a day of fun. And then there's the LOCATION! This cottage is ideally positioned within Margaritaville Resort Orlando, just steps from the resort's incredible amenities. Enjoy access to 7 resort pools, the Fins Up Beach Club, fitness center, resort transportation and shuttle service to the theme parks. The community is also pet-friendly and features Barkaritaville, a dedicated dog park. When you're ready to venture out, you're surrounded by everything that makes this area one of Central Florida's most desirable vacation destinations. Sunset Walk is just steps away, offering restaurants, bars, live entertainment, shopping and more, while Island H2O Water Park is right nearby. Disney, Universal, SeaWorld and Orlando's other major attractions are all just minutes away. Even better, the monthly HOA includes high-speed internet, cable, phone service, daily doorstep trash pickup, landscaping, pest control, a resort shuttle and a shuttle to the parks adding even more convenience to resort living. Whether you're looking for a vacation getaway, second home, full-time residence or a short-term rental investment, this is your opportunity to own a fully furnished cottage in one of Central Florida's most popular resort communities. Pack your flip-flops and come see why life really is better in Margaritaville! Schedule your private showing today!

3054 Pirate Way, Kissimmee

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040

8045 Lost Shaker Lane, Kissimmee
$575,000
4 Beds ⋅ 5 Baths ⋅ O6404095 MLS
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

Listing courtesy of LAKEFIELD REALTY GROUP LLC. 407-383-6497

8080 Dreamsicle Drive, Kissimmee
$459,900
4 Beds ⋅ 3 Baths ⋅ O6395871 MLS
Under contract-accepting backup offers. "LAZY PARROT" is a Charming Cottage at Margaritaville Resort Orlando. This is a Wonderful Community to Live in Full Time, Own a Second Home or Invest in a Vacation Rental Property! Located in PREMIUM RESORT LOCATION Just a Short Walk to All the Amenities! MRO Approved City Furniture "SAIL AWAY" Furniture/Housewares Included in List Price. Beautiful 1539-C Model, 3 Bedrooms, 3 Bathrooms with BONUSROOM and CUSTOM PARROT DESIGN SHUTTERS. Master Suites on BOTH First and Second Floors. Downstairs Suite has French Doors Leading to Tranquil Backyard with Paved Patio, Beautiful Tropical Foliage and Shell Pathways. All Three Bedrooms have KING BEDS! The Furniture is the Original City Furniture MRO Approved and Some Items are No Longer Available to Purchase. Home Features High Capacity Washer and Dryer, "SON OF A SAILOR" Interior Upgrade with "WOOD" Tile Flooring, Upgraded Appliances, QUARTZ Countertops, Ceiling Fans and TANKLESS WATER HEATER. There is an Additional Bonus Room Upstairs with a BUILT IN TWIN BED and TV. Furniture/Housewares Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishwasher, Linens, and so MUCH MORE! 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 Is Not Just A Residence; It's A Lifestyle Choice For Those Who Want To Experience The Best Of Florida Living, Where Every Day Feels Like A Vacation.

8080 Dreamsicle Drive, Kissimmee

Listing courtesy of EXP REALTY LLC. 888-883-8509

2924 Caribbean Soul Drive, Kissimmee
$353,000
3 Beds ⋅ 3 Baths ⋅ S5146209 MLS ⋅ 2924 BLDG.
Under contract-accepting backup offers. 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.

2924 Caribbean Soul Drive, Kissimmee

Listing courtesy of P4L REALTY LLC. 407-845-9189

8056 Dreamsicle Drive, Kissimmee
$390,000
2 Beds ⋅ 3 Baths ⋅ O6387518 MLS
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.

8056 Dreamsicle Drive, Kissimmee

Listing courtesy of LIVE MVRK LLC. 407-756-4563

8017 Surf Street, Kissimmee
$1,275,000
7 Beds ⋅ 9 Baths ⋅ O6386683 MLS
**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

Listing courtesy of LUXE PROPERTIES LLC. 305-809-7650

3052 Parrot Head Place, Kissimmee
$1,349,000
8 Beds ⋅ 9 Baths ⋅ S5143539 MLS
Under contract-accepting backup offers. 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

Listing courtesy of FLORIDA IN MOTION REALTY INC. 407-947-2757

2946 Salted Rim Road, Kissimmee
$570,000
3 Beds ⋅ 3 Baths ⋅ O6356626 MLS
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

Listing courtesy of THE JERRY BARKER GROUP LLC. 407-756-7296

8063 Knee Deep Road, Kissimmee
$379,000
2 Beds ⋅ 2 Baths ⋅ O6334138 MLS
***FABULOUS MARGARITAVILLE RESORT***FANTASTIC RENTAL OR VACATION HOME*** OWN ONE OF THE BEST LEASING FLOORPLANS with a DOWNSTAIRS Bedroom and BATH*** Your opportunity to own a TROPICAL COTTAGE OASIS in Margaritaville Resort Orlando! Enjoy 5 O'clock somewhere everyday!!! The property is perfect as a Primary Residence or use it as an INVESTMENT / VACATION home and be part of the Margaritaville Rental program! The spacious cottage offers 2 Bedrooms/2 Bathrooms and is a short walk or bike ride to all the amenities that Margaritaville Resort has to offer! ALL FURNITURE AND HOUSEWARES INCLUDED IN LIST PRICE! (The furnishings/Housewares are a $15,000 - $20,000 value). Wonderful Key West style furnishings. This Awesome property offers two Primary suites with bathrooms, one on the First Floor with Access to the Outdoor Patio! Second Floor En Suite Bedroom has a King Size Bed, Private Bathroom with a Tub/Shower Combo and a Private Balcony with Seating Area. Upon arriving to the property guests will enjoy the quaint Covered Front Porch, Ceiling Fans, Upgraded Appliances, QUARTZ Countertops and 'Wood' Tile Flooring. Full size Washer and Dryer on First Floor. Backyard has Paved Patio with Table, Chairs. The Turnkey Furniture Package Includes Blinds, Drapes, TVs, Artwork, Kitchen Necessities, Dishes/Glasses, Linens and SO MUCH MORE! A one of a Kind Resort with Multiple Pools, Gym, On-Site Water Park, Sunset Walk Restaurants, Bars, Live Music, Retail and More! MINUTES FROM ALL ORLANDO HAS TO OFFER INCLUDING DISNEY PARKS, UNIVERSAL ORLANDO, SEA WORLD AND THE UP AND COMING EPIC UNIVERSE! Come LIVE, VACATION and INVEST in PARADISE and MARGARITAVILLE!!! If you choose to stay with the same rental company, there are reservations on the books for 2024 and 2025, Or if you want as your primary the bookings can be moved. Schedule a showing today!!

8063 Knee Deep Road, Kissimmee

Listing courtesy of COLDWELL BANKER REALTY. 407-352-1040

3056 Parrot Head Place, Kissimmee
$1,375,000
8 Beds ⋅ 9 Baths ⋅ O6265271 MLS
'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

Listing courtesy of EXP REALTY LLC. 888-883-8509

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The data relating to real estate for sale on this website comes in part from the Broker Reciprocity program of the Dayton Area Board of Realtors® MLS IDX Database. Real estate listings from the Dayton Area Board of Realtors® MLS IDX Database held by brokerage firms other than Coldwell Banker Realty are marked with the IDX logo and are provided by the Dayton Area Board of Realtors® MLS IDX Database. Information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in. Copyright© 2026 Dayton Area Board of Realtors®

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