TOP 30 Best Upscale resort vacations in Kissimmee, 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.

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.

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.

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.

Southern Sands RV Resort is a luxurious 55 Zeman Signature Resort located in Arcadia, Florida. Situated at 11537 Southwest Kissimmee Road, this resort offers top-notch lodging for RV enthusiasts looking for a peaceful and upscale retreat. With spacious RV sites, modern amenities, and a tranquil atmosphere, Southern Sands RV Resort is the perfect destination for those seeking a relaxing and enjoyable stay. Experience the beauty of Florida's Gulf Coast while enjoying the comfort and convenience of this premier RV park.

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.

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.

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.

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.

Royalty1 Vacations is a premier travel agency located at 7700 Westgate Boulevard in Kissimmee, Florida, United States. Offering a variety of vacation packages starting at just $99, Royalty1 Vacations provides incredible savings of up to $980 on getaways for couples and families alike. With a focus on popular destinations such as Williamsburg, Las Vegas, and Gatlinburg, Royalty1 Vacations ensures that every traveler can find their perfect home away from home. At Royalty1 Vacations, guests can experience the luxury and comfort of Westgate Resorts, which offers spacious accommodations with a range of amenities. From exclusive dining options to world-class spas and children's activities, Westgate Resorts provides a memorable vacation experience for everyone. With locations in Orlando, Myrtle Beach, Branson, and more, Westgate Resorts offers something for every traveler, whether they prefer the beach, the mountains, or thrilling attractions.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

RW Hotel is a premier lodging destination located at 4650 West Irlo Bronson Memorial Highway in Kissimmee, Florida. This luxurious hotel offers guests a comfortable and upscale stay with modern amenities and exceptional service. Whether you are visiting for business or pleasure, RW Hotel provides a relaxing and welcoming atmosphere for all travelers. With its convenient location near popular attractions and entertainment venues, guests can easily explore all that Kissimmee has to offer. Book your stay at RW Hotel for a truly unforgettable experience.

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.

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.

Park Royal Orlando is a luxurious resort located on West Orange Boulevard in Kissimmee, Florida. This upscale institution offers guests a serene and tranquil retreat in the heart of the Sunshine State. With spacious accommodations, modern amenities, and impeccable service, Park Royal Orlando provides the perfect setting for a relaxing vacation or a memorable family getaway. Whether you want to lounge by the pool, indulge in a spa treatment, or explore the nearby attractions, Park Royal Orlando has everything you need for a truly unforgettable experience.

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.

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.