Kissimmee Homes with Key West Architectural style

Kissimmee Homes with Key West Architectural style

Welcome to Kissimmee, Florida, a vibrant city nestled in the heart of Osceola County, where sunshine and charm converge to create an idyllic living experience. Known for its close proximity to the world-renowned attractions of Walt Disney World and Universal Studios, Kissimmee offers a delightful blend of small-town warmth and big-city excitement. With lush landscapes, beautiful lakes, and a rich history, this city is not just a destination for tourists but a wonderful place to call home.

One of the standout features of Kissimmee's real estate market is the enchanting Key West architectural style. These homes, characterized by their vibrant colors, inviting porches, and metal roofs, exude a tropical charm that perfectly complements Florida's sunny climate. Key West homes often feature open floor plans, large windows that invite natural light, and lush landscaping, creating a welcoming atmosphere that is both stylish and functional. Imagine sipping your morning coffee on a spacious porch, surrounded by swaying palm trees and the gentle sounds of nature—this is the everyday life that awaits you in a Key West-style home in Kissimmee.

Whether you are a first-time homebuyer, a retiree looking for a peaceful retreat, or a family seeking adventure and community, Kissimmee offers a diverse range of properties to suit your needs. With its unique blend of culture, recreation, and stunning homes, Kissimmee is truly a hidden gem in Florida. Come explore the possibilities and discover your dream home in this enchanting city!

Newest Kissimmee Homes with Key West Architectural style

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
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
$919,000
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
5000 Mangrove Alley Unit 104, Kissimmee
$215,000
1 Beds ⋅ 1 Baths ⋅ Runaway Beach Club Condo SubDv. ⋅ 34746 Zip Code
Welcome to 5000 Mangrove Aly #104 in Kissimmee, Florida! This fantastic property presents a wonderful opportunity to own a modern and stylish fully furnished condominium in a prime location. Whether you are looking for a primary residence or an investment property for either long-term or short-term rental, this property situated in the gated community of Runaway Beach, offers comfort, convenience, and a host of amenities. As you enter, you'll be greeted by a spacious, bright living area with French doors opening onto the private side patio. The open floor plan seamlessly connects the living room, dining area, and kitchen, creating an inviting atmosphere for both relaxing and entertaining. The updated kitchen is well-appointed with modern appliances, ample cabinet space, and a breakfast bar. This condominium features one primary bedroom, which is generously sized and includes a walk-in closet, and a family bathroom with a shower/tub combination. Additional features include a separate laundry closet with a washer and dryer, along with a large storage cupboard. Residents of this community also have access to a range of amenities, including two swimming pools, a hot tub, a fitness center, and a clubhouse. Conveniently located in Kissimmee, this property offers easy access to shopping centers, restaurants, entertainment venues, and major highways.

5000 Mangrove Alley Unit 104, Kissimmee
2968 Caribbean Soul Drive, Kissimmee
$294,000
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
8075 Knee Deep Road, Kissimmee
$650,000
5 Beds ⋅ 6 Baths ⋅ Margaritaville SubDv. ⋅ 34747 Zip Code
Experience the Margaritaville lifestyle in the heart of Kissimmee, Florida, just minutes from Walt Disney World and Central Florida’s top attractions. This spacious 5 bedroom, 5.5 bathroom cottage is located in a premier vacation home community known for its unmatched amenities and vibrant atmosphere. Positioned within close proximity to the resort pool, spa, gym, and entertainment, this home offers both convenience and an elevated guest experience. The interior features upgraded countertops, stainless steel appliances, and wood look tile flooring that blends style with durability. Designed with both comfort and income potential in mind, each bedroom includes its own bathroom access, providing privacy for owners and guests alike. The primary bedroom offers a peaceful retreat with its own en suite bathroom. This home is located in a sold out resort community that allows for short term rentals, making it an ideal investment opportunity, vacation home, or full time residence. Enjoy access to multiple pools, a water park, fitness center, full service spa, and Sunset Walk, where you will find dining, shopping, bars, and live music just moments away. Situated in Kissimmee near Orlando, this property offers easy access to Disney Parks, major roadways, and everything Central Florida has to offer.

8075 Knee Deep Road, Kissimmee
8017 Surf Street, 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
2731 N Poinciana Boulevard Unit 105, Kissimmee
$194,900
3 Beds ⋅ 2 Baths ⋅ Villas At Somerset The SubDv. ⋅ 34746 Zip Code
Priced to sell!! Fully furnished beautifully remodeled 3-bedrrom, 2 full-bath apartment offered fully furnished and move-in ready. This property includes all kitchen appliances, washer & dryer, and waterproof luxury vinyl floor. Condo roof renovated in 2025. Ideal for multiple uses, including primary residence, long-term rental, or short-term rental/Airbnb. Conveniently located near major Orlando attraction parks as Disney World, Universal Orlando, Sea World. In addition, the shopping, dining, and entertainment options are countless. An excellent opportunity for investors or homeowners seeking flexibility, comfort, and a prime location in the heart or Orlando. Community features: pool, jacuzzi, tennis court, sauna, club house, fitness center, community mail box, side walk, business facilities, and convenience stores. Don't wait any longer and turn this house into your Disney vacation home!

2731 N Poinciana Boulevard Unit 105, Kissimmee
9021 Flamingo Key Way, Kissimmee
$510,000
4 Beds ⋅ 4 Baths ⋅ Solara Resort SubDv. ⋅ 34747 Zip Code
THIS HOME IS A MUST SEE!!! Welcome to this stunning 4-bedroom, 3.5-bathroom home, ideally located in the sought-after Solara Resort in Kissimmee. Whether you're looking for a full-time residence or a vacation home investment, this property offers the perfect blend of relaxation and convenience. Situated just off US-192, with quick access to I-4 and US-27, you’re only 8 miles from world-class theme parks and just a short commute to the famous attractions of the Orlando area, including local beaches. Enjoy easy access to premier shopping and dining options along International Drive or at the Prime Outlet Mall. The Solara Resort community offers an unparalleled resort-style living experience with amenities that include an on-site restaurant, coffee bar, beach-style pool, pool bar, fitness center, basketball court, soccer field, volleyball court, gaming stations, sports simulator, yoga lawn, playground, splash pad, water slides, and even a Flowrider sea wave simulator – there's something for everyone! Inside, the home has been beautifully decorated and furnished by professionals with an open floor plan that is perfect for entertaining. The spacious kitchen boasts granite countertops and stainless-steel appliances, making meal prep a true pleasure. The upstairs loft is a media dream, providing ample space for movie nights or relaxation. The dining area seamlessly flows into the outdoor space through sliding doors, leading to your own private pool—ideal for extending your entertainment space. Don’t miss out on this incredible opportunity to own a piece of paradise. Call today and schedule your showing at your convenience!

9021 Flamingo Key Way, Kissimmee
2988 Salted Rim Road, Kissimmee
$475,000
3 Beds ⋅ 3 Baths ⋅ Margaritaville SubDv. ⋅ 34747 Zip Code
Welcome to your own slice of paradise in Margaritaville Resort Orlando , where lifestyle, location, and income potential come together effortlessly . This beautifully designed Cottage Floorplan 1539 C offers 3 bedrooms and 3 full bathrooms, perfectly suited for a vacation home, or high performing short term rental near Walt Disney World . Ideally located within WALKING DISTANCE to the resort pool, spa, fitness center, and premier amenities, this home places you in the heart of one of Kissimmee’s most desirable vacation communities. Inside, the open concept layout creates a bright and inviting atmosphere, featuring upgraded countertops, stainless steel appliances, and stylish wood look tile flooring throughout the main living areas. The spacious primary bedroom offers a private retreat with its own en suite bathroom, while the additional bedrooms are thoughtfully positioned to provide comfort and flexibility for guests. This home is offered FULLY FURNISHED with the MRO approved City Furniture Key West Sunset package, including furnishings, décor, TVs, window treatments, kitchen essentials, linens, and more. Truly turnkey and ready to enjoy or generate immediate rental income. Margaritaville Resort Orlando delivers an unmatched resort experience with multiple pools, a full service spa, fitness center, and direct access to Island H2 O Water Park. Just minutes away, Sunset Walk offers a vibrant mix of dining, entertainment, shopping, and live music. Whether you are looking to relax, invest, or do both, this property offers the perfect opportunity to own in a premier short term rental community near Disney and the best of Central Florida attractions.

2988 Salted Rim Road, Kissimmee
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