TOP 30 Luxury holidays in Kissimmee, Florida

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Holiday Inn Club Vacations at Orange Lake Resort is a luxurious lodging destination located in Kissimmee, Florida, United States. This resort offers spacious accommodations, top-notch amenities, and a wide range of activities for guests of all ages. Whether you're looking to relax by the pool, play a round of golf, or explore the nearby theme parks, this resort has something for everyone. With its convenient location and exceptional service, Holiday Inn Club Vacations at Orange Lake Resort is the perfect choice for your next vacation getaway.

Experience Kissimmee, Florida, located at 215 Celebration Place, is a local government office that invites you to enjoy a world of vacation fun in the heart of Florida. With sunny skies, beautiful rivers, and sparkling lakes, Kissimmee is the perfect destination for adventure and relaxation. Explore world-famous theme parks, outdoor activities, legendary golf courses, and a variety of attractions for all ages. Indulge in delicious dining options, exciting entertainment districts, and vibrant festivals throughout the year. Choose from a wide range of accommodations, from vacation rentals to luxury resorts, in the Vacation Home Capital of the World®. Join hosts Jen Bonner and Ming Chen on The Kissimmee Experience and discover all that this vibrant city has to offer. Embrace diversity and inclusivity at Experience Kissimmee, where all visitors are welcomed with open arms.

Breeze Kissimmee is a vibrant and lively bar located at 7 East Dakin Avenue in the heart of Kissimmee, Florida. Known for its relaxed atmosphere and friendly staff, Breeze Kissimmee offers a wide selection of beverages, including craft cocktails, beer, and wine. Guests can enjoy live music, DJ nights, and special events throughout the week. Whether you're looking for a fun night out with friends or a place to unwind after a long day, Breeze Kissimmee is the perfect spot to kick back and enjoy the breeze.

Majesty Family Villas is a premier real estate and travel agency located at 8920 Majesty Palm Road in Kissimmee, Florida. Our agency specializes in providing luxurious and spacious villas for families looking to make unforgettable memories during their vacation. Each villa is meticulously designed and equipped with modern amenities to ensure a comfortable stay for our guests. Whether you are looking for a relaxing getaway or an action-packed adventure, Majesty Family Villas has the perfect accommodation for you. Book your stay with us today and experience the ultimate vacation experience in the heart of Florida.

Orlando Villas is a premier real estate and travel agency located at 1408 Grandview Boulevard in Kissimmee, Florida. We specialize in providing luxurious vacation rental properties in the Orlando area, offering guests a home away from home during their stay in the Sunshine State. Our dedicated team of professionals is committed to providing top-notch customer service and ensuring that each guest's experience is nothing short of exceptional. Whether you're looking for a cozy villa for a romantic getaway or a spacious home for a family vacation, Orlando Villas has the perfect accommodation for you. Book your dream vacation rental with us today and let us help you create memories that will last a lifetime.

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.

Go Legacy Dunes is a premier lodging, real estate, and travel agency located at 8902 Legacy Court in Kissimmee, Florida. Our institution offers luxurious accommodations in the heart of the Sunshine State, perfect for vacationers and property investors alike. With top-notch amenities and a prime location near all of the area's attractions, Go Legacy Dunes is your go-to destination for a memorable and stress-free stay in Florida. Contact us today to book your next getaway or to explore real estate opportunities in this beautiful part of the United States.

Reunion Vacation Homes is a lodging, real estate, and travel agency located at 7531 Osceola Polk Line Road in Davenport, Florida, United States. Specializing in bringing friends and family together in Orlando Vacation Home Rentals and Anna Maria Island Rentals, Reunion Vacation Homes offers a wide range of vacation rentals in select Orlando area resorts close to Disney® such as Reunion Resort, The Retreat at Champions Gate, Windsor at Westside, and more. With options ranging from 2-3 bedroom condos to 10-14 bedroom luxury villas, there is something for everyone. Whether you're looking for top villa rentals near Disney World® in Kissimmee & Davenport, or luxury mansions in Reunion Resort, Reunion Vacation Homes has you covered. With over 300 luxury villas and condos to choose from, guests can enjoy amenities such as private pools, golf course views, and proximity to major attractions.

Orlando Short Term Rentals is a premier real estate and travel agency located at 1050 Plaza Drive in Kissimmee, Florida. Specializing in providing top-notch short term rental properties in the Orlando area, our agency offers a wide range of accommodations to suit every traveler's needs. Whether you're visiting for a family vacation, business trip, or special event, our team is dedicated to helping you find the perfect rental property to make your stay unforgettable. With a focus on customer satisfaction and personalized service, Orlando Short Term Rentals is your go-to destination for a seamless and enjoyable rental experience in the Sunshine State.

Sun On the Beach is a vibrant and lively institution located on the famous West Irlo Bronson Memorial Highway in Kissimmee, Florida. This establishment is a popular destination for both locals and tourists looking to enjoy delicious food, refreshing drinks, and a laid-back beach atmosphere. Whether you're in the mood for a casual meal, a cold beer, or a tropical cocktail, Sun On the Beach has something for everyone. With its beach-themed décor and friendly staff, this bar and restaurant is the perfect spot to unwind and soak up the Florida sun. Come visit us at 5770 West Irlo Bronson Memorial Highway for a taste of paradise in the heart of Kissimmee.

Gala Gifts is a charming store located at 7733 West Irlo Bronson Memorial Highway in the heart of Kissimmee, Florida. This delightful shop offers a wide variety of unique and beautifully curated gifts for all occasions. From stylish home decor items to thoughtful souvenirs, Gala Gifts has something for everyone. Whether you're looking for a special present or just want to treat yourself, stop by Gala Gifts and discover the perfect gift that will bring joy to your loved ones.

Margaritaville Cottages Orlando is a charming lodging institution located at 8011 Fins Up Circle in Kissimmee, Florida, United States. Nestled in a tropical paradise, this resort offers a relaxing and fun-filled getaway for guests of all ages. The cottages are beautifully decorated in a laid-back island style, creating a cozy and inviting atmosphere. Guests can enjoy a range of amenities including a pool, restaurant, and activities for the whole family. Whether you're looking to unwind by the pool or explore the nearby attractions, Margaritaville Cottages Orlando is the perfect destination for your next vacation.

Encantada Resort Vacation Townhomes by IDILIQ is a luxurious lodging option located at 3070 Secret Lake Drive in Kissimmee, Florida. This resort offers spacious and comfortable self-catering townhomes just outside Walt Disney World, making it the perfect choice for vacationers looking for larger spaces and great amenities. Each townhome at Encantada Resort is individually owned and features a fully equipped kitchen, private patio with a hot tub, and all the facilities needed for a perfect vacation in Orlando. The resort is ideal for families and larger groups, with two, three, and four-bedroom options available.

Orange Lake Resort is a premier lodging destination located at 14201 East Orange Lake Boulevard in Kissimmee, Florida, United States. This expansive resort offers luxurious accommodations surrounded by beautiful landscapes and top-notch amenities. Guests can enjoy spacious villas, multiple pools, golf courses, restaurants, and a variety of recreational activities. Whether you're looking for a relaxing getaway or a fun-filled family vacation, Orange Lake Resort has everything you need for a memorable stay in sunny Florida.

RCI Resort Orange Lake is a luxurious lodging institution located at 8505 West Irlo Bronson Memorial Highway in Kissimmee, Florida, United States. Situated in the heart of the Sunshine State, this resort offers guests a perfect blend of relaxation and excitement. With spacious accommodations, top-notch amenities, and stunning views of the surrounding landscape, RCI Resort Orange Lake is the ideal destination for a memorable vacation. Whether you're looking to unwind by the pool, tee off on the golf course, or explore the nearby attractions, this resort has something for everyone. Book your stay today and experience the ultimate in comfort and convenience at RCI Resort Orange Lake.

Windsor at Westside Resort & Clubhouse is a popular lodging destination located at 2100 Tripoli Court in Kissimmee, Florida. Established in 2015 by Pulte Homes, this resort community offers a unique experience for guests of all ages. The 10,000 sq.ft. clubhouse features a kid's activity center, Tu Casa Bar and Lounge, a game room, and a resort-style pool with a waterslide, lazy river, hot tub, and Kids' water playground. Tu Casa Bar & Lounge offers poolside dining with a variety of delicious food options and a full-service bar serving liquor, beer, wine, and frozen favorites. The resort includes single-family pool homes and townhomes ranging from 4 to 9 bedrooms, perfect for family vacations. With popular attractions like Disney, Sea World, Universal Studios, and Legoland nearby, Windsor at Westside Resort is the ideal destination for your next family trip.

Escape to Regal Oaks Resort Vacation Townhomes by IDILIQ, located at 5780 Golden Hawk Way in Kissimmee, Florida, United States. This institution offers lodging, real estate, and travel agency services. Nestled in the heart of Orlando, our resort is the perfect retreat for families, couples, and groups of friends looking for a magical getaway. Enjoy spacious accommodations, world-class amenities, and a range of activities for the whole family. Unwind in a fully equipped kitchen, relax on your private screened patio, and indulge in the resort's pool oasis. With multiple bedrooms, these vacation homes cater to diverse needs, ensuring a truly extraordinary escape. Staycation savings are available exclusively for Florida and Georgia residents. The resort offers a Cabana Pool Bar for tropical beverages, a family-friendly sports bar and grill, and easy access to popular theme parks and attractions. Dive into the expansive pool, challenge your skills on the tennis and pickleball courts, and enjoy the arcade and market on-site. Regal Oaks Resort is part of the IDILIQ Group of companies, offering luxurious accommodations in sought-after holiday destinations. Experience the perfect blend of comfort and family-friendly fun at Regal Oaks Resort Vacation Townhomes by IDILIQ.

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.

The Storey Lake Clubhouse is a premier facility located at 4715 Kings Castle Circle in Kissimmee, Florida. This luxurious clubhouse offers a wide range of amenities for guests to enjoy, including a state-of-the-art fitness center, a resort-style swimming pool, a lazy river, and a children's splash pad. Guests can also relax in the hot tub or enjoy a meal at the on-site restaurant. For more information about the amenities at Storey Lake Resort, guests can contact the Hideaway Clubhouse at 407-787-8700. Additionally, guests can request a quote for shuttle service to nearby attractions by completing the form on the website.

Prime Mobility VIP is a premier travel agency located at 2719 Holiday Woods Drive in Kissimmee, Florida. Specializing in luxury and VIP travel experiences, our team of experienced professionals is dedicated to providing top-notch service and personalized itineraries for our clients. Whether you are looking for a lavish vacation or exclusive travel arrangements, Prime Mobility VIP is here to make your travel dreams a reality. Contact us today to start planning your next unforgettable journey.

Driftwood Worldgate Resort is a charming lodging establishment located at 3011 Maingate Lane in Kissimmee, Florida, United States. This resort offers a relaxing and comfortable stay for guests looking to explore the nearby attractions such as Walt Disney World and Universal Studios. The resort features spacious rooms, modern amenities, and a beautiful outdoor pool area. With its convenient location and friendly staff, Driftwood Worldgate Resort is the perfect choice for travelers seeking a peaceful retreat in the heart of Florida.

Magic Tree Resort is a charming vacation destination located at 2795 North Old Lake Wilson Road in Kissimmee, Florida. Situated in the heart of the Sunshine State, this resort offers guests a magical experience with its cozy accommodations and top-notch amenities. Whether you're looking to relax by the pool, enjoy a round of golf, or explore the nearby theme parks, Magic Tree Resort has something for everyone. Come and experience the magic for yourself at this unforgettable retreat in the United States.

Welcome to our beautiful 3 bedroom, 3 bathroom, 1678 square foot vacation rental just 5 minutes away from Disneyworld in Kissimmee, Florida. Located at 7576 Sunny Dreams Lane, this resort-style lodging offers a luxurious and convenient stay for families or groups visiting the area. With modern amenities, comfortable furnishings, and a prime location near the most popular attractions, your stay here will be unforgettable. Enjoy the sunny Florida weather and nearby theme parks while staying in this spacious and well-equipped vacation rental.

Oak Plantation Resort is a charming lodging institution located at 4090 Enchanted Oaks Circle in Kissimmee, Florida, United States. Nestled in a peaceful and scenic setting, this resort offers a relaxing retreat for guests looking to unwind and rejuvenate. The spacious accommodations are tastefully decorated and equipped with modern amenities to ensure a comfortable stay. Guests can also enjoy the resort's outdoor pool, fitness center, and other recreational facilities. With its convenient location near popular attractions such as Walt Disney World and Universal Studios, Oak Plantation Resort is the perfect choice for travelers seeking a memorable vacation experience in the Sunshine State.

Runaway Beach Resort by Magical Memories is a charming lodging establishment located at 3001 Bonfire Beach Drive in Kissimmee, Florida. This resort offers a magical escape for guests looking to relax and unwind in the sunny state of Florida. With spacious accommodations, modern amenities, and a prime location just minutes away from popular attractions like Walt Disney World and Universal Studios, Runaway Beach Resort provides the perfect home away from home for families and couples alike. Whether you're lounging by the pool, exploring the nearby theme parks, or simply enjoying the beautiful Florida weather, Runaway Beach Resort by Magical Memories is the ideal destination for your next vacation.

Florida Vacation Villas is a premier lodging, real estate, and travel agency located at 2777 North Poinciana Boulevard in Kissimmee, Florida, United States. Our villas offer luxurious accommodations for vacationers looking to experience the magic of Florida. Whether you're looking for a relaxing getaway or an action-packed adventure, our team is dedicated to providing top-notch service to ensure your stay is unforgettable. With a prime location near popular attractions like Disney World and Universal Studios, Florida Vacation Villas is the perfect choice for your next vacation in the Sunshine State. Book your stay with us today and experience the ultimate Florida getaway!

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.

Florida Fantasy Homes is a premier lodging institution located in the heart of Kissimmee, Florida. Situated at 1050 East Osceola Parkway, our luxurious vacation homes offer the perfect blend of comfort and convenience for travelers visiting the Sunshine State. Whether you're looking for a cozy retreat for a romantic getaway or a spacious accommodation for a family vacation, Florida Fantasy Homes has a variety of options to suit your needs. With top-notch amenities, stunning decor, and proximity to popular attractions like Disney World and Universal Studios, our institution provides the ultimate home away from home experience for guests. Book your stay with us and make your Florida dream vacation a reality.

Havana Services Group - Havana Travel is a comprehensive institution located at 2106 East Osceola Parkway, Kissimmee, Florida, United States. Originally established in January 2012 as Havana Travel in Miami, Florida, the institution has since expanded its services to include accounting, finance, and travel agency offerings. With a strong emphasis on integrity, professionalism, and customer support, Havana Travel has grown alongside its clients, opening offices in Orlando and Jacksonville in 2014 to provide a wider range of services including immigration assistance and notary services. In addition to traditional travel agency services, Havana Services Group now offers a range of business solutions such as company incorporation, expansion, and administrative services. Since 2017, the institution has also welcomed real estate experts to its team, providing clients with access to the best loan rates and assistance with property purchases in the United States.

Storey Lake Resort is a premier real estate agency located at 4827 Romeo Circle in Kissimmee, Florida. This luxurious resort offers a variety of vacation homes and townhouses for sale or rent, perfect for those looking to experience the magic of Orlando. With top-notch amenities such as a lazy river, water slides, fitness center, and on-site dining options, Storey Lake Resort is the ideal destination for those seeking a relaxing and fun-filled getaway in the heart of the Sunshine State. Whether you're looking for a permanent residence, a vacation home, or an investment property, Storey Lake Resort has something for everyone. Come experience the ultimate in resort-style living at Storey Lake Resort.