The 30 Best Florida luxury rentals in Kissimmee, Florida

Caribe Cove Resort in Kissimmee by Vacasa offers luxurious vacation rentals for every getaway. Located at 9000 Treasure Trove Lane in Kissimmee, Florida, this resort is the perfect destination for a relaxing and enjoyable stay. With 53 vacation rentals equipped with internet access, guests can stay connected throughout their trip. The professional housekeeping team at Caribe Cove ensures that each rental is thoroughly cleaned and stocked with amenities, allowing guests to simply settle in and relax. Whether you're looking for a lodging option, real estate agency, or travel agency, Caribe Cove Resort has everything you need for your next getaway. Book your stay at Caribe Cove Condominiums in Kissimmee, FL for a memorable vacation experience.

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.

Ramada by Wyndham Kissimmee Gateway is a charming lodging facility located at 7470 West Irlo Bronson Memorial Highway in Kissimmee, Florida, United States. Our institution offers comfortable accommodations and top-notch amenities for guests to enjoy during their stay. On our website, we prioritize the privacy and preferences of our guests by using cookies for analytical purposes, personalizing content, offering social media functions, and showing personalized advertising based on browsing habits. Guests have the option to set their preferences and choose how their data is used by installing cookies or similar technologies.

Extended Stay America - Orlando - Kissimmee is a comfortable and convenient lodging option located at 7727 West Irlo Bronson Memorial Highway in Kissimmee, Florida. This institution offers spacious and well-equipped rooms that are perfect for long-term stays. Guests can enjoy amenities such as fully equipped kitchens, free Wi-Fi, and on-site laundry facilities. The location is ideal for those looking to explore the attractions of Orlando, as it is close to popular theme parks and shopping areas. Whether visiting for business or leisure, Extended Stay America - Orlando - Kissimmee provides a relaxing and home-like atmosphere for all guests.

Rentals in Emerald Island Resort is a reputable real estate and travel agency located at 8515 Crystal Cove Loop in Kissimmee, Florida, United States. Specializing in vacation rentals within the luxurious Emerald Island Resort, this agency offers a wide range of beautiful properties for guests to choose from. With top-notch customer service and a dedication to providing unforgettable experiences, Rentals in Emerald Island Resort is the perfect choice for those looking to explore the magic of central Florida. Whether you're seeking a cozy villa for a romantic getaway or a spacious home for a family vacation, this agency has something for everyone. Book your stay with Rentals in Emerald Island Resort and make your dream vacation a reality.

Windsor Hills Private Rentals is the official rental website for the Windsor Hills Resort in Kissimmee, Florida. Endorsed and run by the Resort Management Committee, we offer a wide selection of vacation rentals in the most popular resort community in the Orlando area. With no commission or booking fees, you can secure your dream vacation rental directly with the property owner or manager. Our advanced search functionality helps you find the perfect accommodation, whether you're looking for a villa, townhome, or condo. The resort is located just 2 miles from Walt Disney World, making it the ideal location for a family vacation, business event, wedding, or honeymoon. Enjoy the amenities of the Windsor Hills Resort, including a clubhouse, lagoon-style pool, water park, fitness center, playground, and more. With easy access to top golf courses and major theme parks, renting in Windsor Hills puts you in the center of the action. Book your perfect vacation rental property now with Windsor Hills Private Rentals.

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.

Located at 2801 Kissimmee Bay Boulevard in Kissimmee, Florida, the Kissimmee Bay Country Club offers a unique blend of bar, food, health, and restaurant services. Guests can reserve their round of golf online at either Kissimmee Bay or Remington Golf Club, both conveniently located just a short drive from Orlando International Airport and downtown Orlando. Surrounded by stunning oak trees that date back a century, the country club offers a picturesque setting for a relaxing round of golf. The traditional 6,830-yard, par-71 championship course, designed by Lloyd Clifton, features challenging water hazards and friendly Sandhill Cranes.

Hilton Vacation Club Polynesian Isles Kissimmee is a luxurious lodging institution located at 3045 Polynesian Isles Boulevard in Kissimmee, Florida, United States. This tropical paradise offers spacious and comfortable accommodations for guests looking to relax and unwind in style. With top-notch amenities, stunning surroundings, and exceptional service, Hilton Vacation Club Polynesian Isles Kissimmee is the perfect destination for a memorable vacation experience.

Remedy Salon Suites Kissimmee is a beauty salon located at 1621 John Young Parkway, Kissimmee, Florida, United States. This institution offers franchise opportunities for business professionals looking to establish themselves in the beauty industry. The central location of Remedy Kissimmee provides a prime setting in the heart of Kissimmee, making it a convenient backdrop for your business. The facility spans 2,497 square feet and includes 14 private suites, each designed with elegant fixtures and chic décor. The salon offers flexible daily/hourly booth rental options and amenities such as high-speed WiFi, a dedicated receptionist, and key code entry for each suite to ensure a secure and welcoming environment. The suites are equipped with new backwash units, styling stations, and dryers for comfort and functionality.

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.

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.

Nestled in the heart of Kissimmee, Florida, Orlando Vacation Rentals Homes at Storey Lake Resort offers luxurious lodging options for visitors to the area. Whether you're looking for a cozy condo or a spacious villa, this real estate and travel agency has a wide selection of vacation rentals to choose from. With its convenient location near popular attractions like Walt Disney World and Universal Studios, Storey Lake Resort is the perfect home base for your Orlando vacation. Experience the comfort and convenience of a home away from home at this beautiful resort community located at 3131 Paradox Circle.

Windsor Hills Kissimmee Villa is a luxurious vacation rental located at 7757 Tosteth Street in Kissimmee, Florida. This stunning villa offers guests a comfortable and stylish retreat just minutes away from the world-famous attractions of Orlando, including Walt Disney World and Universal Studios. With spacious accommodations, modern amenities, and a private pool, Windsor Hills Kissimmee Villa is the perfect choice for families and groups looking for a memorable stay in the Sunshine State. Enjoy the convenience of a fully equipped kitchen, cozy living areas, and easy access to shopping, dining, and entertainment options. Experience the magic of Florida in comfort and style at Windsor Hills Kissimmee Villa.

Experience the ultimate in luxury at this stunning 6 bedroom, 4 bath villa located in the prestigious Windsor Hills Resort in Kissimmee, Florida. This spacious and beautifully appointed home features top-of-the-line amenities, including a private pool and spa, fully equipped gourmet kitchen, and multiple living and dining areas. Perfect for families or large groups, this villa offers plenty of space to relax and unwind after a day of exploring all that Orlando has to offer. With easy access to theme parks, shopping, and dining, this is the perfect home base for your next vacation in the Sunshine State.

Best Western Plus Kissimmee-Lake Buena Vista South Inn & Suites is a charming lodging option located at 3484 Polynesian Isles Boulevard in Kissimmee, Florida. This institution offers comfortable and modern accommodations, perfect for travelers looking to explore the nearby attractions such as Walt Disney World and Universal Studios. The Inn & Suites features a range of amenities including a sparkling outdoor pool, fitness center, complimentary breakfast, and free high-speed Wi-Fi. With its convenient location and excellent service, Best Western Plus Kissimmee-Lake Buena Vista South Inn & Suites is the ideal choice for a memorable stay in the Sunshine State.

Disney Dream Vacation Rental is your ultimate destination for a magical stay in Kissimmee, Florida. Situated at 182 Hideaway Beach Lane, our institution offers a variety of luxurious lodging options for your dream vacation. As a real estate agency, we provide top-notch accommodations that will make your stay truly unforgettable. Our travel agency services can help you plan the perfect Disney getaway, with convenient access to all the theme parks and attractions in the area. Whether you're looking for a cozy villa or a spacious vacation home, Disney Dream Vacation Rental has the perfect option for you. Book your stay with us today and experience the magic of Disney like never before.

Experience a delightful stay at our charming studio unit located within a hotel with a refreshing pool in Kissimmee, Florida. The address is 5245 West Irlo Bronson Memorial Highway. This cozy accommodation offers a comfortable bed, a fully equipped kitchenette, and a private bathroom. Guests can enjoy access to the hotel amenities including the pool, fitness center, and on-site dining options. Perfect for couples or solo travelers looking for a relaxed and convenient stay near popular attractions in the area. Book your stay with us today!

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!

Endless Summer Florida House is a versatile institution located at 8502 Blue Horizon Court, Kissimmee, Florida, United States. It serves as a lodging, real estate, and travel agency, offering discounted rates for May & June 2024. Whether you are traveling for business or pleasure, Endless Summer provides maximum convenience at competitive rates. The accommodations are flexible, suitable for small or large families and groups. The Kissimmee Florida Vacation Home is a spacious and well-appointed lakefront villa in the gated community of Sunset Lakes. The interior features an open foyer, living room, dining room, family room, full kitchen with new appliances, dinette, laundry room, and attached two-car garage. The five guest bedrooms and three full bathrooms on the second floor include two master bedrooms with en-suite bathrooms.

Windsor Hills Rental Villas is a premier lodging option located at 2600 North Old Lake Wilson Road in Kissimmee, Florida. This institution offers beautifully remodeled GROUND FLOOR condos within the sought-after Windsor Hills Resort, just a stone's throw away from the Magic Kingdom. The fully furnished condos feature tropical and Disney themes, flat-panel LCD televisions, high-speed DSL, and all necessary housewares and linens. Guests can enjoy a SOUTH FACING POOL with no rear neighbors, providing a private and relaxing atmosphere. Additionally, Windsor Hills boasts an in-house theater room for entertainment. With its close proximity to Disney and various entertainment options, Windsor Hills is the perfect choice for a magical vacation in Orlando. Visit Windsor Hills at 2600 Old Lake Wilson Road, Kissimmee, Florida 3474.

Experience luxury at its finest in this stunning 3 bedroom, 2 bath condo located in the prestigious Windsor Hills community in Kissimmee, Florida. This beautifully appointed accommodation features modern amenities, high-end furnishings, and a spacious layout perfect for families or groups of friends. Enjoy the convenience of a fully equipped kitchen, plush bedding, and a private balcony with breathtaking views. Take advantage of the resort-style amenities including a pool, fitness center, and clubhouse. With its prime location near Disney World and other major attractions, this condo is the perfect choice for your next vacation getaway.

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.

Element Luxury Apartments is a premier living destination located at 4100 Arrow Ridge Place in Kissimmee, Florida, United States. Our apartments offer a perfect blend of modern design, upscale amenities, and breathtaking views. Residents can enjoy luxurious features such as gourmet kitchens, spacious living areas, and private balconies. The community also boasts a resort-style pool, fitness center, and on-site management for convenience. Experience the epitome of luxury living at Element Luxury Apartments.

Viva Orlando Rentals is a premier real estate agency located at 610 Sycamore Street in Kissimmee, Florida. Specializing in vacation rentals in the Orlando area, Viva Orlando Rentals offers a wide range of properties to choose from, including luxury villas, condos, and townhomes. With a commitment to providing top-notch customer service and personalized attention to each client, Viva Orlando Rentals is dedicated to helping visitors find the perfect accommodation for their stay in the sunshine state. Whether you're planning a family vacation, a romantic getaway, or a group trip, Viva Orlando Rentals has the perfect property for you. Book your dream vacation rental with Viva Orlando Rentals today and experience the magic of Orlando in style and comfort.

Kissimmee Court Apartments is a charming residential community located at 2239 McLaren Circle in Kissimmee, Florida. Our apartments offer modern amenities and spacious floor plans, making it the perfect place to call home. Residents can enjoy a relaxing atmosphere, beautifully landscaped grounds, and convenient access to shopping, dining, and entertainment options. With a friendly and professional management team on-site, Kissimmee Court Apartments provides a comfortable and enjoyable living experience for all of our residents.

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.

Jeeves Florida Rentals is a premier real estate and travel agency located at 7796 West Irlo Bronson Memorial Highway in Kissimmee, Florida. We specialize in helping you find the perfect Orlando vacation home rental with our powerful search features and exclusive collection. Our luxury dream homes in the Sunshine State feature private pools, movie theaters, bowling alleys, and arcades for the ultimate vacation experience. Book with us directly and receive a free package valued at $750! Our vacation home resorts are strategically located for easy access to Disney World and all Orlando theme parks, offering top amenities, security, and privacy. Trust Jeeves Florida Rentals for a truly luxurious Orlando vacation rental experience.

Tropical Villas Orlando Vacation Rentals & Property Management is a premier real estate and travel agency located at 2950 Loopdale Lane in Kissimmee, Florida, United States. We specialize in providing luxurious vacation rentals in the tropical paradise of Orlando, offering a wide range of properties to suit every traveler's needs. Our dedicated team of professionals is committed to ensuring a seamless and unforgettable vacation experience for our guests, from booking to check-out. Whether you're looking for a cozy condo or a spacious villa, we have the perfect accommodation for your dream vacation in Orlando. Contact us today to start planning your next getaway!

The Diamond on the Island at Emerald Island Resort is a luxurious vacation rental house located in Kissimmee, Florida. Situated in the prestigious Emerald Island Resort, this stunning property offers the perfect combination of comfort, style, and convenience for your Disney vacation. With spacious accommodations, modern amenities, and a prime location just minutes away from Walt Disney World, this rental house is the ideal choice for families and groups looking to experience the magic of Orlando. Book your stay at The Diamond on the Island and make unforgettable memories on your next Florida getaway. Contact our real estate and travel agency located at 8578 Sunrise Key Drive to learn more about our exclusive vacation rental options.