TOP 10 Vacation rentals and stays in Kissimmee, Florida

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.

Windsor Hills Resort is a luxurious vacation destination located in Kissimmee, Florida, just a short drive away from the world-famous theme parks of Orlando. Situated at 2600 North Old Lake Wilson Road, this resort offers a wide range of amenities and activities for guests of all ages to enjoy. From the stunning pool area with water slides and a hot tub, to the fitness center, tennis courts, and children's playground, there is something for everyone at Windsor Hills Resort. The spacious and beautifully appointed accommodations provide a comfortable home away from home, with fully equipped kitchens, private balconies, and stylish decor. Whether you're looking for a relaxing retreat or an action-packed adventure, Windsor Hills Resort is the perfect choice for your next vacation in sunny Florida.

Runaway Beach Club is a charming lodging institution located at 3000 Bonfire Beach Drive in Kissimmee, Florida. This beach-themed resort offers guests a relaxing and comfortable stay in the heart of the Sunshine State. With spacious accommodations, a sparkling swimming pool, and easy access to the nearby attractions of Kissimmee and Orlando, Runaway Beach Club is the perfect choice for a fun-filled vacation. Whether you're looking to soak up the sun on the beach or explore the nearby theme parks, this institution provides the perfect home base for your Florida getaway.

Margaritaville Resort Orlando is a luxurious island-inspired escape located at 8000 Fins Up Circle in Kissimmee, Florida. This resort offers high-end accommodations, world-class dining, and entertainment, as well as relaxing facilities and amenities. Situated just minutes away from popular attractions like Walt Disney World Resort, Universal Orlando Resort, and SeaWorld Orlando, Margaritaville Resort Orlando is the perfect destination for your dream getaway. Choose from modern guest rooms, spacious suites, private cottages, and villas to suit your preferences. Relax at the soothing spa, beach club, or Island H2O Water Park, and explore Sunset Walk for shopping, dining, and entertainment options. With a variety of room options available, including pool-view rooms, suites, cottages, and villas, Margaritaville Resort Orlando has something for everyone.

Westgate Town Center Resort in Kissimmee, Florida, offers fully furnished villas perfect for families visiting Walt Disney World Resort and other nearby attractions. With onsite amenities, dining options, and a water park, this resort is the ideal choice for a fun-filled vacation. Florida and Georgia residents can save up to 10% on their stay. Enjoy Shipwreck Island Water Park and delicious dining options during your stay. Please note that features and amenities may change. Westgate Owners can enjoy additional benefits through the World of Westgate Loyalty Program. This offer includes 50,000 points that can be redeemed for future purchases at Westgate Resorts.

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.

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.

Disney's Animal Kingdom Villas - Jambo House is a luxurious lodging option located at 2901 Osceola Parkway in Kissimmee, Florida, United States. Choose from a variety of accommodations, including villa-style options and rooms with Concierge service. Enjoy shared amenities such as pools, dining options, and recreational activities during your stay. Relax at the 11,000-square-foot Uzima Pool, surrounded by tropical foliage and featuring a waterslide and whirlpool spas. Kids will love the Samawati Springs Pool with its waterslide, whirlpool spas, and Uwanja Camp water playground. Explore award-winning dining options offering African specialties and classic American favorites.

Solara Resort is a luxurious lodging institution located at 9002 Sunset Palms Terrace in Kissimmee, Florida, United States. As soon as you enter through the guarded gates, you will be greeted with a world-class luxury experience. The 18-acre grounds offer top-notch amenities such as sports fields, a grand clubhouse, and an expansive water park, all designed to make your stay in Orlando magical and memorable. Each vacation villa at Solara Resort features over 4700 square feet of living space, up to 9 bedrooms, 6.5 baths, a private spa pool, outdoor lanai, and more. The sleek design, high ceilings, and designer furnishings create the perfect vacation oasis. The resort offers endless activities for guests of all ages, from sports and recreation to family-friendly fun.

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.

Terra Verde Resort is a luxurious lodging destination located at 109 Madiera Beach Boulevard in Kissimmee, Florida. Situated in the heart of the Sunshine State, this resort offers a tranquil oasis for guests looking to relax and unwind. With beautiful accommodations, top-notch amenities, and a prime location near popular attractions like Disney World and Universal Studios, Terra Verde Resort is the perfect choice for a memorable vacation experience. Whether you're lounging by the pool, exploring the nearby theme parks, or simply enjoying the peaceful surroundings, Terra Verde Resort provides a truly unforgettable stay in the United States.

Bellavida Resort is a luxurious lodging option located at 1172 Marcello Boulevard in Kissimmee, Florida. Situated in the heart of the Sunshine State, this resort offers a serene and relaxing atmosphere for guests looking to unwind and enjoy a peaceful vacation. With spacious accommodations, top-notch amenities, and a convenient location near popular attractions such as Disney World and Universal Studios, Bellavida Resort is the perfect choice for travelers seeking comfort and convenience during their stay in Florida. Whether you're looking to relax by the pool, explore the nearby theme parks, or simply enjoy the beautiful surroundings, Bellavida Resort has everything you need for a memorable and enjoyable vacation experience.

Located at 8545 West Irlo Bronson Memorial Highway in Kissimmee, Florida, The Berkley, Orlando is a stunning condominium-style resort perfect for family vacations. Situated near Orlando's top theme parks, the resort offers easy access to family-friendly restaurants and fun activities for all ages. With a grand clubhouse, state-of-the-art fitness center, large swimming pool, lap pool, and private movie theater, there is something for everyone to enjoy. The Berkley, Orlando also provides shuttle service to the nearby theme parks, making it convenient for guests to explore the area. The resort has been awarded a Gold Crown Status with RCI, recognizing its high standards in housekeeping, maintenance, hospitality, and guest services. Additionally, The Berkley, Orlando has received accolades from Tripadvisor, including the Travelers Choice Award and the Hall of Fame Award for consistent excellence.

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 [email protected] for booking inquiries. Experience the beauty of Magic Village Yards and make unforgettable vacation memories in this tranquil oasis in the heart of Orlando.

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.

Magical Windsor Hills Retreat is a luxurious vacation rental located at 2507 Archfeld Boulevard in Kissimmee, Florida, United States. This enchanting retreat offers a truly magical experience for guests looking to relax and unwind in a beautiful setting. With spacious accommodations, top-notch amenities, and stunning views, Magical Windsor Hills Retreat is the perfect destination for families, couples, and friends looking to create unforgettable memories. Whether you're lounging by the pool, exploring nearby attractions like Disney World and Universal Studios, or simply enjoying the peace and tranquility of the surroundings, this retreat is sure to leave you feeling rejuvenated and refreshed. Book your stay at Magical Windsor Hills Retreat today and experience the magic for yourself.

Reunion Resort Water Park, located at 7593 Gathering Drive in Kissimmee, Florida, is a top tourist attraction and amusement park for visitors of all ages. With a variety of exclusive amenities and features, including private swimming pools and movie theaters, our vacation homes offer a unique and luxurious stay. The Water Park at Reunion Resort features a zero entry pool, 1,000 foot lazy river, large waterslide, kids splash zone, beach area, cabanas for rent, and a full bar with frozen drinks. Guests can enjoy complimentary tubes for the lazy river and participate in family-friendly contests for prizes.

Windsor Island Resort is a luxurious vacation destination located at 1115 Aloha Boulevard in Davenport, Florida, United States. This stunning resort offers a range of accommodations including spacious villas and townhouses, all beautifully designed and fully equipped for a comfortable stay. Guests can enjoy a variety of amenities such as a sparkling swimming pool, fitness center, tennis courts, and a clubhouse with game room. The resort is conveniently located near popular attractions like Walt Disney World and Universal Studios, making it the perfect choice for families and couples looking for a memorable getaway in the Sunshine State.

Escape to the magical world of Disney at our Water Park Heated Pool located at the Storey Lake Hideaway Club House in Kissimmee, Florida. Book directly with us for the best rates and enjoy a comfortable stay in our luxurious accommodations. Whether you're looking for a relaxing getaway or an action-packed adventure, our resort has something for everyone. Don't miss out on the opportunity to experience the magic of Disney right at your doorstep. Visit us at 4815 Love Storey Lane and make memories that will last a lifetime.

Windsor Hills Pool View Condo is a luxurious lodging option located at 7650 Comrow Street in Kissimmee, Florida, United States. This three-bedroom, two-bathroom condo is situated near Walt Disney World and offers stunning poolside views. Guests can enjoy the resort's amenities such as the clubhouse, theater, game room, and full-size gym. The condo is Disney themed throughout, with stuffed Disney characters adding to the magical atmosphere. With its proximity to popular attractions like Magic Kingdom, Epcot, and Universal Orlando, Windsor Hills is the perfect choice for a family-friendly vacation. The property is meticulously cleaned and sanitized following the guidelines of leading health agencies, ensuring a safe and comfortable stay for all guests. With its unbeatable location and top-notch amenities, Windsor Hills Pool View Condo is a popular choice for families visiting the Orlando area.

Launchpad's Landing is a luxurious 5 bedroom vacation home located in the gated resort community of Windsor Hills, just 2 miles from Disney World in Kissimmee, Florida. With two king bedrooms, a queen room, and two rooms with twin beds, all with private ensuite bathrooms, this home is perfect for multigenerational family groups. The backyard oasis features a private pool, spillover spa, screened lanai, propane grill, and plenty of space to relax. The fully equipped kitchen, high-speed wifi, cable, and smart TVs throughout the home ensure a comfortable stay. Guests can enjoy the resort amenities including a lagoon pool, waterpark, playgrounds, sport courts, and more. Just minutes from Disney World and other Orlando attractions, Launchpad's Landing is the ultimate family home for your vacation. Book now to experience a magical stay at Launchpad's Landing!

Rentyl Resorts is a luxurious lodging institution located at 8011 Fins Up Circle in Kissimmee, Florida. Our resort offers top-notch accommodations and amenities to ensure a comfortable and unforgettable stay for our guests. Whether you're looking for a relaxing getaway or an action-packed vacation, Rentyl Resorts has something for everyone. Come and experience the ultimate in hospitality and relaxation at our stunning resort in the heart of Florida.

Villas At Fortune Place is a charming lodging institution located at 1201 Simpson Road in Kissimmee, Florida, United States. Nestled in a serene and picturesque setting, this resort-style property offers spacious and well-appointed villas perfect for families and groups looking for a comfortable and relaxing vacation getaway. Guests can enjoy a range of amenities including a swimming pool, hot tub, fitness center, and outdoor recreational facilities. With its convenient location near popular attractions such as Walt Disney World and Universal Studios, Villas At Fortune Place is the ideal choice for a memorable and enjoyable stay in the Sunshine State.

Villa By The Castle is a top-rated luxury vacation rental located at 2608 Daulby Street in Kissimmee, Florida. This 6-bedroom, 4-bathroom villa is just 2 miles from Disney World in the beautiful Windsor Hills Resort. The villa is equipped with a private pool and spa, a game room with a pool table and air hockey, and a great room with a 70" 3D LED Smart TV. With amenities like TVs in every bedroom, baby gear, and a fully equipped kitchen, Villa By The Castle provides a comfortable and welcoming home for your Disney vacation. As owner-operated, you'll have direct communication with us throughout your stay. Windsor Hills is the closest resort community to Disney World, offering resort-style amenities and a convenient location. Book your stay at Villa By The Castle and experience the best of Kissimmee and Orlando.

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.

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.

The Disney Lillian House at Terra Verde Resort is a charming and cozy lodging option located at 117 Madiera Beach Boulevard in Kissimmee, Florida. This beautifully decorated house offers a unique Disney-themed experience for guests looking to immerse themselves in the magic of Disney. As a real estate agency, the Disney Lillian House also offers opportunities for guests to invest in their own piece of Disney magic by purchasing a vacation home in the Terra Verde Resort community. With a prime location near all of Orlando's major attractions, this resort is the perfect place to own a vacation property.

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.

Welcome to Olivia's Dream Villa, a luxurious vacation rental located at 2657 Dinville Street in Kissimmee, Florida. This stunning property is the perfect getaway for families and groups looking to experience the magic of Orlando's theme parks and attractions. Featuring spacious bedrooms, a fully equipped kitchen, a private pool, and a game room, Olivia's Dream Villa offers all the comforts of home in a beautiful and serene setting. Guests can relax on the sun loungers by the pool, enjoy a BBQ in the outdoor dining area, or unwind in the hot tub after a long day of exploring the nearby attractions.

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.