Osceola County Homes with Key West Architectural style

Osceola County Homes with Key West Architectural style

Welcome to Osceola County, a vibrant gem nestled in the heart of Central Florida, where the enchanting city of Kissimmee beckons with its rich history and diverse cultural landscape. Known for its warm climate and friendly atmosphere, Osceola County offers a unique blend of urban amenities and natural beauty, making it an ideal place to call home.

Kissimmee is renowned for its proximity to world-famous attractions, including Walt Disney World and Universal Studios, yet it maintains a charming small-town feel. With picturesque parks, scenic lakes, and a plethora of recreational activities, residents can enjoy the best of both worlds—adventure and tranquility.

One of the standout architectural styles you’ll find in this region is the captivating Key West style. Characterized by its vibrant colors, metal roofs, and spacious porches, these homes exude a laid-back coastal charm that perfectly complements the sunny Florida lifestyle. Key West homes in Kissimmee often feature open floor plans, allowing for seamless indoor-outdoor living, ideal for entertaining friends and family or simply soaking up the sun.

Imagine sipping your morning coffee on your porch, surrounded by lush tropical landscaping, or hosting a barbecue in your backyard oasis. The Key West architectural style not only provides aesthetic appeal but also embodies a sense of community and relaxation that is synonymous with life in Osceola County.

Whether you’re seeking a primary residence or a vacation getaway, Kissimmee’s Key West homes offer a delightful escape where you can create lasting memories. Embrace the vibrant culture, stunning landscapes, and welcoming spirit of Osceola County—your perfect home awaits!

Newest Osceola County Homes with Key West Architectural style

4590 E Firefly Lane, St Cloud
$439,990
4 Beds ⋅ 3 Baths ⋅ Waterlin SubDv. ⋅ 34772 Zip Code
Under Construction. The Magnolia floor plan offers a comfortable two-story layout featuring 4 bedrooms and 2.5 bathrooms, ideal for those seeking both space and functionality. The main floor includes a spacious family room adjacent to the dining area, with a covered patio extending from the Living room for outdoor enjoyment. The kitchen provides direct access to the dining space, and a separate laundry room sits conveniently near the two-car garage entrance. The primary suite, located on the first floor, includes a private bathroom and a walk-in closet, creating a peaceful retreat. Upstairs, a versatile loft area is surrounded by three additional bedrooms, making it perfect for a cozy lounge or play area. The Magnolia balances everyday convenience with thoughtful design for a welcoming home environment. Sample Images

4590 E Firefly Lane, St Cloud
4435 E Firefly Lane, St Cloud
$623,106
5 Beds ⋅ 4 Baths ⋅ Waterlin SubDv. ⋅ 34772 Zip Code
Virtually Staged. Under Construction. Beautiful Ellington floor plan in Waterlin! This spacious 5-bedroom, 3.5-bath home features a first-floor primary suite, dedicated office, large game room, and open-concept living spaces. Enjoy peaceful pond views from the backyard and plenty of room for work, play, and entertaining. A perfect blend of comfort, flexibility, and scenic waterfront living. Sample Images

4435 E Firefly Lane, St Cloud
2707 River Creek Lane, St Cloud
$505,000
3 Beds ⋅ 2 Baths ⋅ Del Webb Sunbridge Ph 1d SubDv. ⋅ 34771 Zip Code
This upgraded Prosperity floor plan by Del Webb Pulte is a charming craftsman style 3-bedroom, 2-bath home with a front porch offering that tropical paradise vibe. This bright open-concept design connects the kitchen, dining, and gathering areas with stone fireplace , creating an inviting space for daily living and entertaining. With ample amounts of windows and glass sliders letting in natural light. Premium ceiling fans throughout. Top-Tier Aristocrat soft-close cabinetry, under cabinet lighting, quartz countertops, upgraded faucets, and a spacious walk-in pantry. Included is a whole house water treatment system. Upgraded Porcelain tile throughout the home. Professionally designed custom closet in the Master bedroom. Masterfully blends timeless charm with modern Smart Home Technology with the Central Control System allowing remote monitoring and automation of lighting, security, and smart thermostat. Professional custom lighting inside and out. This home comes with Tesla Solar Panels and Tesla Power Wall with a transferable warranty...giving current owners a $0 electric bill and Whole House Battery Power Backup! The 2 car garage has insulated garage doors, two large overhead storage rack and epoxy flooring. Out back you have an east facing screened-in Lanai with an extended patio and black aluminum fencing offering a cozy tropical paradise, and a large backyard for a Pool! Del Webb Sunbridge, a premier 55+ community, residents enjoy an unmatched lineup of amenities including a 27,000 sq ft clubhouse, Tavern & Grille, 24 hour guard-attended entry, two pools, tennis and pickleball courts, dog park, fitness center and a full-time lifestyle director offering a robust calendar of social events and activities.

2707 River Creek Lane, St Cloud
2939 Castaway Lane, Kissimmee
$330,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks SubDv. ⋅ 34747 Zip Code
Welcome to resort-style living in the heart of Margaritaville Resort Orlando! This bright and spacious 2-bedroom townhome with a bonus room is located in the desirable Rolling Oaks community, just minutes from Walt Disney World. The flexible bonus room is currently set up with a twin bed, making it a great additional sleeping space, guest room, or cozy retreat. Inside, you’ll find stylish wood-look tile, quartz countertops, upgraded appliances, wood stairs, high ceilings, a private owner’s closet, and plenty of space to relax and unwind. Whether you’re looking for a full-time residence, a Florida getaway, or a short-term rental investment, this property offers incredible flexibility. Margaritaville Resort delivers the vacation lifestyle with multiple resort-style pools, restaurants and bars, a fitness center, full-service spa, walking trails, gated security, and convenient access to Sunset Walk, where shopping, dining, entertainment, and Island H2O Water Park are practically at your doorstep. With exterior maintenance, landscaping, and lawn care included, you can spend less time worrying about upkeep and more time enjoying everything Central Florida has to offer!

2939 Castaway Lane, Kissimmee
8036 Lost Shaker Lane, Kissimmee
$435,000
4 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 6 SubDv. ⋅ 34747 Zip Code
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
224 Cypress Fork Trail, St Cloud
$529,990
4 Beds ⋅ 4 Baths ⋅ Waterlin 45'S SubDv. ⋅ 34772 Zip Code
Virtually Staged. Under Construction. The Anna Maria with Bonus floorplan is an expansive two-story home designed to accommodate a growing family, offering five bedrooms and three and a half bathrooms. On the main floor, you'll find a spacious great room adjacent to a well-appointed dining room and kitchen, creating an ideal space for gatherings. The primary suite, featuring a large walk-in closet and private bath, is thoughtfully positioned for privacy. An additional bedroom and a flexible bonus room on the second floor provides ample space for everyone. Sample Image

224 Cypress Fork Trail, St Cloud
1445 Fairview Circle, Kissimmee
$548,800
4 Beds ⋅ 5 Baths ⋅ Reunion Ph 2 Prcl 3 SubDv. ⋅ 34747 Zip Code
NEW PRICE! No rear neighbors, just a private screened pool and a peaceful conservation view. Welcome to Patriots Landing, where this coastal-inspired home sits inside the gates of Reunion Resort, just minutes from Walt Disney World. Inside, 2,764 square feet of well-planned living space offers 4 bedrooms and 4 full bathrooms. The first floor opens to a bright living and dining area with high ceilings, crown molding, and an electric fireplace, flowing into a kitchen with granite countertops, stainless steel appliances, and a pantry. A first-floor guest bedroom with its own full bath is ideal for visitors. Upstairs, the spacious primary suite is joined by two additional bedrooms, each with access to its own full bathroom, so everyone has their own space. Outside, the private screened pool is the heart of the home, made for relaxing, entertaining or simply enjoying the quiet of the preserve. A convenient outdoor pool bath keeps wet feet and towels out of the main living areas. Reunion Resort is one of Central Florida’s most sought-after resort communities, known for championship golf courses designed by Arnold Palmer, Tom Watson and Jack Nicklaus, resort-style pools, a water park with a lazy river, tennis and pickleball courts and dining. Whether you are looking for a primary residence, a vacation retreat, or an investment property, this home delivers space, privacy and location. Offered below its 2026 appraised value, this is an exceptional opportunity to own in Reunion Resort.

1445 Fairview Circle, Kissimmee
200 Cypress Fork Trail, St Cloud
$646,990
6 Beds ⋅ 4 Baths ⋅ Waterlin SubDv. ⋅ 34772 Zip Code
Virtually Staged. Under Construction. The Avalon with Bonus Room by Dream Finders Homes offers 6 bedrooms, 4 bathrooms, and incredible flexibility for today's lifestyle. Featuring a first-floor primary suite plus three additional main-level bedrooms, this thoughtfully designed home provides space for everyone. Upstairs, enjoy a large bonus/game room along with two additional bedrooms and a full bath. Located in the sought-after Waterlin community, this home is perfect for entertaining, multi-generational living, and everyday comfort. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.

200 Cypress Fork Trail, St Cloud
4458 E Firefly Lane, St Cloud
$643,990
5 Beds ⋅ 4 Baths ⋅ Waterlin SubDv. ⋅ 34772 Zip Code
Virtually Staged. Under Construction. Beautiful Ellington floor plan by Dream Finders Homes in Waterlin! This spacious 5-bedroom, 3.5-bath home features a first-floor primary suite, dedicated office, large game room, and open-concept living spaces. Enjoy peaceful pond views from the backyard and plenty of room for work, play, and entertaining. A perfect blend of comfort, flexibility, and scenic waterfront living. The sample photos included are of the model home and are meant to showcase the craftsmanship and design quality.

4458 E Firefly Lane, St Cloud
8117 Surf Street, 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
185 Longview Avenue, Kissimmee
$899,000
4 Beds ⋅ 4 Baths ⋅ Celebration North Village Unit 5 SubDv. ⋅ 34747 Zip Code
Welcome to 185 Longview Avenue, an exceptionally upgraded residence located in the highly desirable Celebration North Village community of Celebration, Florida. Perfectly positioned on a charming corner lot, this beautifully curated 4-bedroom, 3 full bath, 1 half bath home offers 2,035 heated square feet and 2,404 total square feet of elevated living with timeless curb appeal, designer finishes, and a level of refinement rarely found in this price point. From the moment you arrive, the home makes an unforgettable first impression with classic Celebration architecture, a full-width covered front porch, white picket fencing, mature landscaping, blooming crepe myrtles, and a picturesque tree-lined street setting. The premium corner-lot placement enhances the home’s presence, natural light, and sense of privacy while capturing the storybook charm Celebration is known for. Inside, the home has been thoughtfully transformed with a sophisticated modern-luxury aesthetic. Wide plank flooring flows throughout the main living spaces, complemented by crisp neutral walls, substantial baseboards, crown molding, upgraded trim details, designer lighting, recessed lighting, custom window treatments, upgraded interior doors, black hardware accents, and beautiful accent lighting throughout the home that creates a warm, polished, and elevated atmosphere. The open-concept living area is both elegant and functional, offering a seamless connection between the family room, dining area, and kitchen. Expansive windows fill the home with natural light, while the upgraded lighting package and clean architectural lines give the space a refined, high-end feel. A separate flex room provides valuable additional space ideal for a home office, study, playroom, fitness space, media room, or guest overflow, giving the layout the versatility today’s buyers are searching for. The kitchen is a true showpiece, designed with both everyday living and entertaining in mind. Featuring white shaker-style cabinetry, crown-detailed upper cabinets, quartz-style countertops, a dramatic waterfall island, stainless steel appliances, designer backsplash, upgraded fixtures, glass-front display cabinetry, wine glass storage, generous counter space, and bar seating, this space delivers the elevated kitchen experience expected in a luxury Celebration home. Additional designer touches include sliding barn doors, custom millwork-inspired details, a stylish beverage station with built-in storage, cohesive finishes throughout, and a bright neutral palette that feels fresh, timeless, and move-in ready. Every detail has been selected to create a home that feels intentional, curated, and far beyond builder-basic. With 4 bedrooms, 3.5 bathrooms, a flex room, multiple living and dining spaces, and a highly functional layout, this home offers flexibility for full-time living, guests, remote work, or multigenerational needs. The home also features an EV charger, adding modern convenience and additional value for today’s lifestyle. Located in Celebration North Village, residents enjoy one of Central Florida’s most iconic and desirable master-planned communities, known for its charming architecture, walkable lifestyle, parks, trails, community amenities, dining, shopping, events, and close proximity to Walt Disney World, major highways, Orlando attractions, and everyday conveniences.

185 Longview Avenue, Kissimmee
2968 Caribbean Soul Drive, Kissimmee
$284,000
2 Beds ⋅ 3 Baths ⋅ Rolling Oaks Ph 7 SubDv. ⋅ 34747 Zip Code
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
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