The 30 Best Upscale vacation rentals in Kissimmee, Florida

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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.

Wyndham Vacation Resorts Reunion at Orlando is a luxurious lodging facility located at 7593 Gathering Drive in Kissimmee, Florida, United States. This resort offers spacious and well-appointed accommodations, including suites and villas, perfect for families and couples looking to enjoy a relaxing vacation in the Orlando area. Guests can take advantage of the resort's amenities, such as multiple swimming pools, a fitness center, on-site dining options, and easy access to nearby attractions like Walt Disney World and Universal Studios. With its convenient location and upscale accommodations, Wyndham Vacation Resorts Reunion at Orlando is the perfect destination for a memorable getaway.

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.

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.

Paradise Palms Resort is a luxurious lodging destination located at 8950 Paradise Palms Boulevard in Kissimmee, Florida, United States. This tropical paradise offers guests a relaxing and upscale stay with a range of amenities including a stunning pool, fitness center, clubhouse, and more. The spacious accommodations are beautifully decorated and fully equipped with everything you need for a comfortable stay. Whether you're looking for a family-friendly vacation spot or a romantic getaway, Paradise Palms Resort is the perfect choice for your next trip to Florida.

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 7430 Brooklyn Drive in Kissimmee, Florida, the Magic Village Views, Trademark Collection by Wyndham offers a chic and contemporary sanctuary just a mile away from Disney Parks. With floor-to-ceiling windows providing soothing views of the surrounding gardens, guests can enjoy a magical vacation experience in fully equipped villas that accommodate up to 6 or 8 people comfortably. The spacious accommodations include luxury bedding, furnished patios, free Wi-Fi, and free parking. The institution offers exclusive hotel services, including concierge, clubhouse, multilingual staff, cleaning services, and more to enhance guests' stay. ADA defined service animals are welcome, but no other pets are allowed. Guests must be 21 years of age with a valid ID for check-in, along with a refundable deposit for incidentals and a one-time cleaning fee per villa per stay.

7521 Mourning Terraces at Reunion - Regal Managers is a luxurious lodging institution located at 7521 Mourning Dove Circle in Kissimmee, Florida, United States. Managed by Regal Managers, this establishment offers top-notch accommodations with stunning views and impeccable service. Whether you are visiting for a relaxing getaway or a special event, 7521 Mourning Terraces at Reunion is the perfect choice for a memorable stay. With its elegant design, convenient location, and exceptional amenities, this institution ensures a truly regal experience for all guests.

Orange Lake Country Club is a luxurious resort located in Kissimmee, Florida. Situated at 8505 West Irlo Bronson Memorial Highway, this stunning property offers a range of world-class amenities and accommodations for guests to enjoy. From spacious villas to championship golf courses, Orange Lake Country Club provides a relaxing and upscale atmosphere for visitors looking to unwind and experience the best of central Florida. Whether you're looking to relax by the pool, hit the links, or explore nearby theme parks, Orange Lake Country Club offers something for everyone. Experience the ultimate in relaxation and luxury at this premier resort destination.

Gaylord Palms Resort & Convention Center is a luxurious lodging establishment located in Kissimmee, Florida. Situated at 6000 West Osceola Parkway, this resort offers a unique blend of upscale accommodations and world-class amenities. With its stunning architecture inspired by the grandeur of Florida's history and lush tropical landscapes, guests are transported to a paradise unlike any other. The resort boasts spacious rooms and suites, multiple dining options, a full-service spa, a water park, and a state-of-the-art convention center perfect for hosting events of all sizes. Whether you're visiting for a family vacation, a romantic getaway, or a business conference, Gaylord Palms Resort & Convention Center promises an unforgettable experience in the heart of the Sunshine State.

Experience luxury living at its finest at the Luxury 3 Bedroom Condo on Reunion Resort, Orlando Condo 3484. Located at 304 1110 Sunset View Circle in Kissimmee, Florida, this stunning lodging option offers a spacious and beautifully designed three-bedroom condo that is perfect for families or groups looking for a comfortable and upscale accommodation in the heart of Orlando. With top-of-the-line amenities, including a fully equipped kitchen, luxurious bathrooms, and access to the resort's exclusive facilities, guests can enjoy a truly unforgettable stay. Whether you're looking to relax by the pool, play a round of golf, or explore the nearby theme parks, this condo has everything you need for a memorable vacation in the Sunshine State.

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.

Condo Centre Court Haven is a luxurious lodging option located at 1358 Centre Court Ridge Drive in Kissimmee, Florida. This beautiful 3-bedroom unit is part of the prestigious Reunion resort, offering guests a comfortable and upscale stay. The condo features spacious rooms, modern amenities, and stunning views of the surrounding area. Whether you're visiting for a family vacation or a romantic getaway, Condo Centre Court Haven is the perfect choice for your stay in the Sunshine State.

Club Wyndham Cypress Palms is a luxurious resort located at 5324 Fairfield Lake Drive in Kissimmee, Florida. This institution offers upscale lodging accommodations for travelers looking to experience the magic of Orlando and its world-renowned theme parks. As a real estate and travel agency, Club Wyndham Cypress Palms provides guests with top-notch service and amenities to ensure a memorable stay. Enjoy spacious suites, on-site dining options, and easy access to popular attractions in the area. Whether you're looking for a relaxing getaway or an action-packed vacation, Club Wyndham Cypress Palms has everything you need for the perfect Florida escape.

Elevated at Sonoma Resort by Park Square Homes is a luxurious lodging destination located at 3901 Sonoma Boulevard in Kissimmee, Florida. This stunning resort offers guests a truly elevated experience with upscale accommodations, top-notch amenities, and impeccable service. Whether you're looking for a relaxing getaway or a fun-filled vacation, Elevated at Sonoma Resort has everything you need to make your stay unforgettable. From spacious rooms and suites to a sparkling pool and fitness center, this resort has it all. Come and experience the ultimate in comfort and hospitality at Elevated at Sonoma Resort by Park Square Homes.

Villa del Sol is a charming lodging institution located at 2605 West Osceola Parkway in Kissimmee, Florida. This cozy retreat offers a peaceful and relaxing atmosphere for guests looking to escape the hustle and bustle of everyday life. With comfortable accommodations and friendly staff, Villa del Sol provides a home away from home for visitors exploring the nearby attractions of Kissimmee and the greater Orlando area. Whether you're visiting for a family vacation or a romantic getaway, Villa del Sol is the perfect place to unwind and recharge.

King Palm Villa is a luxurious vacation rental located at 8063 King Palm Circle in Kissimmee, Florida. This stunning villa offers guests a tranquil and elegant retreat, complete with spacious living areas, a fully equipped kitchen, private pool, and beautiful outdoor space. Perfect for families or groups looking for a relaxing getaway, King Palm Villa provides all the comforts of home while being just a short drive away from Orlando's world-famous theme parks and attractions. With its convenient location and upscale amenities, King Palm Villa is the perfect choice for a memorable Florida vacation.

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 Estates at Lake Cecile is a luxurious residential community located at 4717 Everglades Circle in Kissimmee, Florida. This stunning property offers a serene and picturesque setting with beautiful views of Lake Cecile. The Estates at Lake Cecile boasts spacious and well-appointed homes with modern amenities and upscale finishes. Residents can enjoy resort-style living with access to a swimming pool, fitness center, and clubhouse. The community is conveniently located near shopping, dining, and entertainment options, making it the perfect place to call home in the heart of Florida.

Secret Lake Resorts is a luxurious vacation destination nestled in the heart of Kissimmee, Florida. Located at 3176 Feltrim Place, this exclusive resort offers a tranquil escape from the hustle and bustle of everyday life. With stunning views of a serene lake, guests can relax and unwind in style. The resort features a range of upscale accommodations, including spacious villas and cozy cottages, all equipped with modern amenities. Guests can enjoy a variety of on-site activities, such as swimming in the crystal-clear pool, fishing in the lake, or simply lounging in the sun. With its convenient location near popular attractions like Walt Disney World and Universal Studios, Secret Lake Resorts is the perfect choice for a memorable vacation in 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.

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.

Heritage Key Villas is a luxurious resort located at 2089 Heritage Key Boulevard in Kissimmee, Florida, United States. This stunning property offers spacious and beautifully appointed villas, perfect for families or groups looking for a comfortable and stylish accommodation option. Guests can enjoy a range of amenities including a sparkling swimming pool, a fitness center, and a clubhouse. The resort is conveniently located near popular attractions such as Walt Disney World and Universal Studios, making it the ideal base for exploring all that central Florida has to offer. Experience the ultimate in relaxation and convenience at Heritage Key Villas.

Orlando Luxury Stays dba is a real estate and travel agency located at 5245 West Irlo Bronson Memorial Highway in Kissimmee, Florida, United States. We offer 5-star luxury homes for corporate rentals, extended stays, vacation getaways, and more. Our properties provide quality accommodations, superior amenities, and subtle touches to make you feel at home. From bedding and bathroom linens to kitchenware and large screen Smart TVs with free Prime Video, we have everything you need for a comfortable stay. Located just 15 minutes from Disney and SeaWorld and 20 minutes from Universal Studios, our properties are the perfect home base for your adventures. Situated in The Loop, you'll be surrounded by dining, shopping, and entertainment options. Whether you're in town for a Disney vacation, business trip, or romantic getaway, our upscale and stylish lodgings provide a blissful place of rest. Book now for the perfect stay in Kissimmee.

Windsor at Westside is a luxurious resort-style community located at 2100 Tripoli Court in Kissimmee, Florida. This stunning institution offers a range of upscale amenities including a clubhouse, fitness center, swimming pool, and sports courts. The beautifully designed homes feature modern finishes and spacious layouts, perfect for families and vacationers alike. With its prime location near Disney World and other major attractions, Windsor at Westside is the perfect destination for those seeking a relaxing and enjoyable stay in the Sunshine State.