The 30 Best Upscale housing in Kissimmee, Florida

Euphoria Fish House is a charming seafood restaurant located at 8000 Fins Up Circle in Kissimmee, Florida. Known for its fresh and delicious seafood dishes, Euphoria Fish House offers a diverse menu featuring a variety of fish, shellfish, and other seafood options. The restaurant's cozy atmosphere and friendly staff make it the perfect spot for a casual meal or a special occasion. Whether you're a seafood lover or just looking to try something new, Euphoria Fish House is sure to leave you feeling satisfied and craving more.

Charley's Steak House is a renowned dining destination located at 2901 Parkway Boulevard in Kissimmee, Florida. Known for its upscale atmosphere and mouthwatering steaks, this restaurant is a favorite among locals and tourists alike. Indulge in a delectable menu featuring prime cuts of beef, fresh seafood, and decadent desserts. The skilled chefs at Charley's Steak House use only the finest ingredients to create unforgettable culinary experiences for guests. Whether you're celebrating a special occasion or simply craving a delicious meal, Charley's Steak House is the perfect choice for a memorable dining experience.

Ohana House, located at 2631 Daulby Street, Kissimmee, Florida, is the ultimate Disney World rental house just 5 minutes away from the magical theme park. This 6 bedroom, 4 bathroom pool villa at Windsor Hills Resort combines hints of Disney's Polynesian Resort with a modern, upscale hotel feel. Completely renovated, Ohana House is a popular choice for families visiting Disney, Universal, or exploring Florida. This luxury vacation house comfortably sleeps 13 and features a fully-equipped kitchen, multiple large TVs, a private heated pool and spa-tub overlooking the lake, and a Star Wars themed game room with arcade games, video games, foosball, and air hockey. The house also boasts three professionally designed themed bedrooms: Moana, Disney, and Pirates of the Caribbean. Magical hints of Disney can be found throughout, including hidden Mickeys.

Champions Village Kissimmee is a premier institution located at 8660 West Irlo Bronson Memorial Highway in Kissimmee, Florida. This vibrant community offers luxury living with a range of amenities including a clubhouse, fitness center, swimming pool, and more. The spacious apartments are beautifully designed and feature modern finishes, making it the perfect place to call home. Additionally, Champions Village Kissimmee is conveniently located near shopping, dining, and entertainment options, providing residents with everything they need right at their fingertips. Experience the ultimate in luxury living at Champions Village Kissimmee.

Cobblestone of Kissimmee is a premier institution located at 1100 Cobblestone Circle in Kissimmee, Florida, United States. Our facility offers top-notch amenities and services for our residents, including spacious living quarters, gourmet dining options, and a variety of recreational activities. Our dedicated staff is committed to providing exceptional care and support to ensure the well-being and comfort of all residents. Come experience the luxury and tranquility of Cobblestone of Kissimmee today.

Disney World House Rental is a luxurious real estate and travel agency located at 8578 Sunrise Key Drive in Kissimmee, Florida, United States. This stunning property offers guests a truly magical vacation experience, with top-notch amenities and a prime location just a 4-mile drive from Disney World's Animal Kingdom Theme Park. The house features beautiful vinyl plank flooring, high-quality pool and spa heating, and a private pool deck surrounded by lush flowering plants. Guests can enjoy the spa/Jacuzzi, high-speed Wi-Fi, and over 100 TV channels on the 7 LED HD Smart TVs. The 6-bedroom, 5 ½ bathroom house can accommodate up to 18 guests, with 4 master suites and 2 children's bedrooms. The upscale furnishings and elegant decor create a warm and inviting atmosphere throughout the 2900 square foot property. The fully stocked kitchen and spacious family room with vaulted ceilings provide the perfect space for relaxing and entertaining. Outside, guests can enjoy the South-facing pool and lanai, with comfortable loungers and a safety fence for young children. The Emerald Island Resort Clubhouse offers additional amenities, including a heated pool and spa, fitness room, Tiki Bar, and nature walking trail. With 24/7 security and a range of entertainment options, Disney World House Rental is the perfect choice for a magical vacation in Florida.

Reunion Resort & Golf Club is a luxurious lodging institution located at 7593 Gathering Drive, Kissimmee, Florida, United States. Our vacation homes offer a refined and unique stay with exclusive features and amenities ranging from 3 to 15 bedrooms. The resort features three signature golf courses, a 5-acre water park, tennis center, and a variety of dining options. With seven swimming pools, two playgrounds, and a range of activities, Reunion Resort is the ultimate family-friendly vacation destination. Enjoy delicious cuisines at various restaurants on-site, and explore nearby attractions such as Walt Disney World®, SeaWorld Orlando, and Universal Orlando Resort. Choose from a selection of villas with one to three bedrooms, or vacation homes with three to 14 bedrooms, each offering a unique living experience. The resort also features a water park, fitness classes, and various activities for guests to enjoy. Host your next event at Reunion Resort, which offers a stunning setting for business conferences, golf retreats, or social celebrations. With its prime location and upscale amenities, Reunion Resort is the perfect destination for an unforgettable vacation experience.

Located in Kissimmee, Florida, Quality Vacation Homes offers a range of beautiful and comfortable lodging options for those looking to enjoy a relaxing and luxurious vacation. Our vacation homes are fully equipped with all the amenities needed for a comfortable stay, including spacious living areas, fully equipped kitchens, and private pools. Whether you're looking for a cozy retreat for a romantic getaway or a spacious home for a family vacation, Quality Vacation Homes has the perfect accommodation for you. Our prime location allows easy access to all the attractions and activities that Kissimmee has to offer, making it the ideal choice for your next vacation. Book your stay with us today and experience the ultimate in quality vacation living.

BR77 Brazilian Steakhouse is a premier dining destination located at 3228 Margaritaville Boulevard in Kissimmee, Florida. As a top-notch Brazilian steakhouse, we offer a unique and authentic dining experience where guests can indulge in a variety of succulent meats cooked to perfection on skewers over an open flame. Our upscale atmosphere, attentive service, and mouthwatering menu make us a must-visit restaurant for those looking to experience the flavors of Brazil in the heart of the United States. Join us for a culinary journey like no other at BR77 Brazilian Steakhouse.

7593 Chophouse is a fine dining restaurant located at 7593 Gathering Drive in Kissimmee, Florida, offering a unique and upscale dining experience. With a menu featuring fresh seafood, steaks, and a variety of other delicious options, there is something to please every palate. The restaurant boasts an extensive wine list and signature cocktail menu to complement your meal perfectly. In addition to the main dining area, 7593 Chophouse also offers a rooftop restaurant called Eleven, where guests can enjoy small plates and craft cocktails while taking in breathtaking views of Orlando. Live entertainment with a DJ on Fridays and a musician on Saturdays adds to the vibrant atmosphere.

Eskina Restaurant & Bar is a vibrant and lively establishment located in Kissimmee, Florida. Situated at 5749 West Irlo Bronson Memorial Highway, this restaurant and bar offers a unique dining experience for locals and tourists alike. With a diverse menu featuring a variety of delicious dishes and a well-stocked bar serving up refreshing drinks, Eskina is the perfect spot to unwind and enjoy a meal with friends or family. The cozy atmosphere and friendly staff make it a popular choice for those looking for a fun and relaxed dining experience.

Old Hickory Steakhouse is a premier dining destination located in Kissimmee, Florida. Situated at 6000 West Osceola Parkway, this upscale restaurant offers a refined ambiance and a menu featuring the finest cuts of steak. Guests can indulge in perfectly cooked steaks, seafood dishes, and decadent desserts while enjoying impeccable service in an elegant setting. Whether you're celebrating a special occasion or simply looking for a memorable dining experience, Old Hickory Steakhouse is the perfect choice for a luxurious meal in Kissimmee.

2 Brother’s Steakhouse is a premier dining destination located in Kissimmee, Florida. Situated at 16 East Dakin Avenue, this upscale restaurant offers a unique and delectable steakhouse experience. With a focus on high-quality ingredients and expertly prepared dishes, 2 Brother’s Steakhouse is the perfect spot for steak lovers and food enthusiasts alike. From juicy, perfectly cooked steaks to mouthwatering sides and desserts, every bite at this restaurant is sure to delight your taste buds. Whether you're celebrating a special occasion or simply looking for a delicious meal, 2 Brother’s Steakhouse is a must-visit culinary gem in the heart of Kissimmee.

Villa Italiano Chophouse is a charming restaurant located in Kissimmee, Florida. Situated at 7700 Westgate Boulevard, this establishment offers a unique dining experience with a menu that combines classic Italian cuisine with delicious chophouse dishes. Guests can enjoy a cozy and inviting atmosphere while savoring expertly prepared meals made with the finest ingredients. Whether you're in the mood for a juicy steak or a flavorful pasta dish, Villa Italiano Chophouse has something for everyone. Come and indulge in a memorable dining experience at this top-rated restaurant in Kissimmee.

Ette Hotel Orlando is a luxurious lodging and spa located at 3001 Sherberth Road in Kissimmee, Florida. Nestled in the heart of the Sunshine State, this upscale institution offers guests a tranquil retreat surrounded by lush landscapes and top-notch amenities. Whether you're looking to relax by the pool, indulge in a rejuvenating spa treatment, or explore the nearby attractions like Walt Disney World and Universal Studios, Ette Hotel Orlando provides the perfect blend of comfort and convenience for your stay in the United States.

Magic Village Yards, Trademark Collection by Wyndham is a luxury concierge-style community located at 3151 Pantanal Lane in Kissimmee, Florida, United States. Offering 3 and 4 bedroom villas with exclusive services, privacy, and comfort, this upscale lodging option is just 2 minutes away from Disney’s Animal Kingdom Park. The villas feature stainless steel kitchens, stylish furnishings, luxury bedding, and private, furnished patios with BBQ grills. With amenities expected of the finest private homes, guests can enjoy a relaxing stay with the benefits of upscale hotel services. The multilingual staff, concierge, clubhouse, cleaning services, and other amenities will enhance your experience. ADA defined service animals are welcome, but no other pets are allowed. Guests must be 21 years of age with a valid ID to check-in, and a refundable deposit for incidentals is required. A cleaning fee applies to all stays. Magic Village Yards is the perfect setting for special events or group trips, with a concierge staff ready to tailor your visit to meet your specific needs. Contact reservations@magicvillage.com for booking inquiries. Experience the beauty of Magic Village Yards and make unforgettable vacation memories in this tranquil oasis in the heart of Orlando.

Located at 8011 Fins Up Circle in Kissimmee, Florida, the Margaritaville Store is the perfect place to kick off your dream getaway at Margaritaville Resort Orlando. Offering high-end accommodations, world-class dining, and entertainment, as well as relaxing facilities and amenities, this island-inspired escape is just minutes away from all the major attractions in Central Florida. Choose from modern guest rooms, spacious suites, private cottages, and villas to suit your relaxation style. Indulge in spa treatments, relax at the beach club, and explore the Sunset Walk for shopping, dining, and entertainment options. Dive into adventure at the Island H2O Water Park, open from March through November.

Welcome to The Suite Retreat at Windsor Hills, located in Kissimmee, Florida. Our luxury 5 bedroom, 5 bathroom villa is the perfect accommodation for your next vacation. Situated in the prestigious, guard gated Windsor Hills Resort, you will be just minutes away from Disney and other top attractions. As our guest, you will have complimentary access to the resort's 5-star amenities, including a water park and double Olympic-sized, zero-entry pool. Our villa features a private screened pool with a spillover spa and covered lanai, complete with complimentary pool heat and a BBQ. Family game nights are covered in our game room, equipped with a 125-inch theater screen, Xbox Series S, arcade games, pool table with ping pong topper, and air hockey table. Kids will love our Harry Potter and Mickey & Friends themed bedrooms, along with the Cupboard Under the Stairs.

AVIA Apartments at Reedy Creek is a modern and luxurious residential complex located at 3020 Reedy Creek Boulevard in Kissimmee, Florida. This upscale institution offers a range of spacious and beautifully designed apartments, complete with top-of-the-line amenities and stunning views of the surrounding area. Residents can enjoy resort-style living with access to a sparkling swimming pool, state-of-the-art fitness center, and lush landscaped grounds. Situated in a prime location, AVIA Apartments at Reedy Creek is just a short drive away from shopping, dining, entertainment, and major attractions, making it the perfect place to call home in the vibrant city of Kissimmee.

The Lucent at Sunrise Apartments is a new luxury apartment community located at 4950 Lunar Lane in Kissimmee, Florida. This stunning complex offers studio, one, two, three, and four bedroom apartments for rent, each meticulously designed with high-end finishes and modern amenities. Residents of The Lucent at Sunrise can enjoy a range of exceptional amenities, including a lazy river with three waterfalls, two resort-style pools, steam rooms, sauna, a massage room, dog splash pads, fitness centers, an on-site barista, 24-hour concierge, and two dog parks. The complex is also committed to sustainability, incorporating energy-efficient features and environmentally-friendly practices.

Belleza Apartments is a luxurious residential complex located at 1365 West Donegan Avenue in Kissimmee, Florida, United States. Our apartments offer modern amenities and stylish design, providing residents with a comfortable and convenient living experience. The property features a swimming pool, fitness center, and beautifully landscaped grounds. With easy access to shopping, dining, and entertainment options, Belleza Apartments is the perfect place to call home in the vibrant city of Kissimmee.

Fountains at San Remo Court is a luxurious senior living community located at 840 Perth Place in Kissimmee, Florida. Our beautifully landscaped grounds feature tranquil fountains and lush gardens, creating a peaceful and serene environment for our residents to enjoy. Our upscale amenities include spacious apartments, gourmet dining options, fitness center, swimming pool, and a variety of social and recreational activities. Our dedicated staff provides personalized care and support to ensure that each resident enjoys a comfortable and fulfilling lifestyle. Experience the ultimate in senior living at Fountains at San Remo Court.

Solamar Apartment Homes is a luxurious residential institution located at 1851 Encantado Way in Kissimmee, Florida, United States. Residents can enjoy five-star resort-style amenities such as a beautifully designed club house, a sparkling swimming pool, and a bark park for their furry companions. The interior of the apartments features stunning granite countertops, elegant vinyl floors, and private balconies with breathtaking views of the night sky. Nearby, residents can explore various walking trails, parks, and playgrounds for outdoor recreation. Additionally, the community is conveniently close to shopping, dining, and entertainment options. Come join our community at Solamar Apartment Homes and experience the ultimate in upscale living.

Altis Shingle Creek is a luxurious apartment community located at 4350 West Osceola Parkway in Kissimmee, Florida. This upscale institution offers residents a resort-style living experience with top-notch amenities including a sparkling swimming pool, fitness center, clubhouse, and lush landscaping. The spacious apartments are beautifully designed with modern finishes and feature gourmet kitchens, walk-in closets, and private balconies or patios. Altis Shingle Creek is conveniently located near major highways, shopping centers, and entertainment options, making it the perfect place to call home in the vibrant city of Kissimmee.

Tiffany Square Apartments is a luxurious residential community located at 333 West Columbia Avenue in Kissimmee, Florida. Our apartments offer modern amenities, spacious floor plans, and a convenient location near shopping, dining, and entertainment options. Residents can enjoy a resort-style pool, fitness center, and beautifully landscaped grounds. Our professional management team is dedicated to providing exceptional service and creating a comfortable living environment for our residents. Experience upscale living at Tiffany Square Apartments in Kissimmee, Florida.

Polo Run Apartments offers a pleasant living environment in Kissimmee, Florida. Located just minutes away from Disney World and Universal Studios, our complex provides a distinctive, contemporary lifestyle for our residents. Our apartment homes are designed to offer quality, convenience, and comfort, meeting the needs of those seeking an exceptional community. With modern conveniences and a quiet, exclusive setting, Polo Run is the perfect place to call home. Come experience the difference at Polo Run Apartments. Contact us at 407-847-8004 or polorun1@hotmail.com for more information.

Polo South Apartments is a luxurious residential community located at 2109 Polo Club Drive in Kissimmee, Florida. Our apartments offer modern amenities and spacious floor plans, perfect for individuals and families looking for a comfortable and convenient living space. Residents can enjoy access to a sparkling swimming pool, fitness center, and beautiful landscaping throughout the property. With a prime location near shopping, dining, and entertainment options, Polo South Apartments provides the perfect blend of relaxation and convenience. Experience upscale living in the heart of Kissimmee at Polo South Apartments.

19 South Apartments is a premier residential community located at 3050 Station Square in Kissimmee, Florida. Situated in the heart of the vibrant city, our apartments offer modern amenities and spacious floor plans for comfortable living. Residents can enjoy a variety of on-site facilities including a swimming pool, fitness center, and clubhouse. With easy access to dining, shopping, and entertainment options, 19 South Apartments is the perfect place to call home in Kissimmee.

The Grand at Westside is a luxurious and modern institution located at 8917 Tiberian Drive in Kissimmee, Florida, United States. This premier facility offers top-notch amenities and services for residents, including spacious living areas, upscale dining options, a state-of-the-art fitness center, and beautiful outdoor spaces. With a focus on providing a comfortable and upscale living experience, The Grand at Westside is the perfect place to call home in the heart of Kissimmee.

Simpson Ridge Apartments is a modern and luxurious residential complex located at 2300 Simpson Ridge Circle in Kissimmee, Florida. Our apartments offer spacious floor plans, upscale amenities, and a convenient location near shopping, dining, and entertainment options. Residents can enjoy a resort-style pool, fitness center, and community clubhouse. With beautifully landscaped grounds and top-notch customer service, Simpson Ridge Apartments is the perfect place to call home in the vibrant city of Kissimmee.