TOP 30 Luxury holidays in Orlando, Florida

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The Best Vacation Homes is a top-rated real estate and travel agency located at 13574 Village Park Drive in Orlando, Florida, United States. We specialize in providing luxury vacation homes for rent in the Orlando area, perfect for families, couples, or large groups looking for a comfortable and convenient place to stay during their visit to the Sunshine State. Our properties are meticulously maintained and offer a range of amenities to make your vacation truly unforgettable. Whether you're planning a trip to Disney World, Universal Studios, or simply want to relax and enjoy the Florida sun, The Best Vacation Homes has the perfect accommodation for you. Contact us today to book your dream vacation home!

Vista Cay By Millenium is a luxurious lodging institution located at 4874 Cayview Avenue in Orlando, Florida. This stunning property offers guests a perfect blend of comfort and convenience, with spacious and elegantly designed accommodations. Whether you're visiting for business or pleasure, Vista Cay By Millenium provides a tranquil oasis in the heart of the bustling city. Enjoy top-notch amenities, impeccable service, and breathtaking views of the surrounding area. Experience a truly unforgettable stay at Vista Cay By Millenium.

All Vacation Dreams is a premier real estate and travel agency located at 6965 Piazza Grande Avenue in Orlando, Florida. Our vacation homes are the perfect place to create lasting memories with friends and loved ones. Stay near the magic in our homes and experience the ultimate vacation experience. Choose a vacation rental for your next trip to Florida and find your dream villa to start your magical moments. All Vacation Dreams is the best choice for your vacation, providing top-quality homes and exceptional customer service since 2002.

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.

New Smyrna Beach Vacation Rentals by Vacasa is a real estate and travel agency located at 4493 South Atlantic Avenue in New Smyrna Beach, Florida, United States. Offering a variety of vacation homes that are perfect for a relaxing getaway in the Sunshine State, our rentals provide a small town feel while still being close to some of the world's most famous attractions. With 20 of our homes allowing dogs, 125 with internet access, and professional housekeepers on staff to ensure everything is clean and stocked for your arrival, our New Smyrna Beach vacation rentals are the ideal choice for your next trip.

InnHouse Vacation Rentals is a premier real estate and travel agency located at 5021 Gateway Avenue in Orlando, Florida, United States. We specialize in providing top-quality vacation rental properties for visitors looking to experience the magic of Orlando. Our expert team is dedicated to helping guests find the perfect accommodation to suit their needs and preferences, ensuring a comfortable and enjoyable stay. Whether you're planning a family vacation, a romantic getaway, or a group trip, we have a wide selection of properties to choose from. Trust InnHouse Vacation Rentals to make your Orlando vacation unforgettable.

Crest Villas is a luxurious residential community located at 4731 North Pine Hills Road in Orlando, Florida. Nestled in a serene and picturesque setting, Crest Villas offers top-notch amenities and spacious living spaces for its residents. The community features beautifully landscaped grounds, a sparkling swimming pool, a fitness center, and a clubhouse for social gatherings. With easy access to shopping, dining, and entertainment options, Crest Villas provides the perfect blend of comfort and convenience for its residents. Experience upscale living at Crest Villas in the heart of Orlando.

Ravello is a charming Italian restaurant located at 10100 Dream Tree Boulevard in Lake Buena Vista, Florida, United States. Known for its delicious and authentic Italian cuisine, Ravello offers a cozy and inviting atmosphere perfect for a romantic dinner or a gathering with friends and family. With a menu featuring a wide variety of pasta dishes, wood-fired pizzas, and decadent desserts, Ravello is sure to satisfy your cravings for traditional Italian fare. Come experience the flavors of Italy at Ravello today!

Kona Island is a charming food institution located at 1600 Seven Seas Drive in Orlando, Florida, United States. This delightful restaurant offers a variety of delicious dishes that will transport you to the beautiful shores of Hawaii. From fresh seafood to tropical cocktails, Kona Island provides a unique dining experience that is sure to satisfy your cravings for island flavors. Come and enjoy the laid-back atmosphere and friendly service at Kona Island today!

The Grande Cove is a vibrant and inviting establishment located in the heart of Orlando, Florida. As a combination bar, food, and restaurant venue, The Grande Cove offers a diverse and delicious menu that is sure to satisfy any craving. Whether you're looking to enjoy a refreshing cocktail with friends, indulge in a mouthwatering meal, or simply relax in a cozy atmosphere, The Grande Cove has something for everyone. Come experience the warm hospitality and tasty offerings at this must-visit institution in Orlando.

Caribbean One Stop is a vibrant and inviting restaurant located in the heart of Orlando, Florida. Our establishment offers a unique dining experience that captures the essence of Caribbean cuisine. From flavorful jerk chicken to mouthwatering seafood dishes, our menu is filled with delicious options that will transport you to the sunny shores of the Caribbean. Whether you're looking for a quick bite to eat or a leisurely meal with friends and family, Caribbean One Stop is the perfect destination. Come visit us at 2117 West Colonial Drive and indulge in the flavors of the islands.

Angels Restaurant & Catering is a charming dining establishment located at 2215 West Oak Ridge Road in Orlando, Florida. Known for its delicious cuisine and excellent service, this restaurant offers a wide range of delectable dishes that are sure to satisfy any palate. Whether you're looking for a casual meal with friends or planning a special event, Angels Restaurant & Catering is the perfect choice. With a warm and inviting atmosphere, friendly staff, and top-notch catering services, this institution is a favorite among locals and visitors alike. Come experience the culinary delights of Angels Restaurant & Catering for yourself!

Caravan Road is a charming restaurant located at 2901 Osceola Parkway in Orlando, Florida. Specializing in delicious and authentic cuisine, this institution offers a culinary journey like no other. From flavorful dishes to tantalizing desserts, Caravan Road is the perfect destination for food enthusiasts looking to explore new and exciting flavors. With a welcoming atmosphere and top-notch service, guests are sure to have a memorable dining experience at this unique establishment. Come and embark on a culinary adventure at Caravan Road today!

LakeHouse is a charming restaurant located at 1 Grand Cypress Boulevard in Orlando, Florida. Nestled in a picturesque setting, this institution offers a unique dining experience with stunning views of the lake. Serving up delicious food in a cozy atmosphere, LakeHouse is the perfect spot for a romantic dinner or a casual meal with friends. Whether you're craving fresh seafood, juicy steaks, or flavorful salads, LakeHouse has something for everyone. Come and enjoy a memorable dining experience at this hidden gem in Orlando.

The Dymond Experience is a unique institution located at 2501 North Orange Blossom Trail in Orlando, Florida, United States. Specializing in food and restaurant services, we also offer exclusive event planning services that will exceed your expectations. From catering to entertainment and decorations, we will work with you to create a truly unforgettable event. Our team at The Dymond Experience has meticulously crafted every detail to ensure that your event is enjoyable and memorable. Whether it's a wedding, graduation party, birthday dinner, or any other special occasion, we are dedicated to making it a success.

Kres Chophouse is a premier dining destination located in the heart of downtown Orlando, Florida. Situated at 17 West Church Street, this upscale restaurant offers a sophisticated and elegant atmosphere for guests to enjoy a high-end dining experience. Specializing in top-quality steaks and chops, Kres Chophouse prides itself on serving only the finest cuts of meat, expertly prepared by their talented chefs. The menu also features a variety of seafood options, appetizers, and decadent desserts. With impeccable service and a stylish ambiance, Kres Chophouse is the perfect spot for a special occasion or a memorable night out in Orlando.

Woodlands is a charming and inviting restaurant located at 6040 South Orange Blossom Trail in Orlando, Florida. This institution offers a warm and welcoming atmosphere for guests to enjoy delicious and authentic cuisine. With a focus on serving high-quality food made with fresh ingredients, Woodlands is a popular destination for those looking to experience the flavors of India. Whether you are craving traditional Indian dishes or looking to try something new, Woodlands has something for everyone. Come and indulge in a culinary journey at this esteemed institution in the heart of Orlando.

Fleming's Prime Steakhouse & Wine Bar is a sophisticated and elegant dining establishment located in Winter Park, Florida. Situated at 933 North Orlando Avenue, this restaurant offers a unique blend of high-quality steaks and an extensive selection of fine wines. Guests can enjoy a luxurious dining experience in a warm and inviting atmosphere, perfect for special occasions or casual outings. With its impeccable service and top-notch cuisine, Fleming's Prime Steakhouse & Wine Bar is a must-visit destination for food and wine enthusiasts in the United States.

Mundi is a food institution located at 10449 Moss Park Road in Orlando, Florida. Known for its super good burgers and the best dogs in Orlando, Mundi offers a wide variety of delicious food options. Customers rave about the excellent service and the variety of sauces available, with the corn sauce being a favorite among many. If you're looking for a fantastic dining experience, Mundi comes highly recommended by all who have visited.

Summer House is a charming restaurant located in Orlando, Florida, United States. Nestled in a cozy corner, this institution offers a delightful dining experience with a menu filled with delicious and fresh seasonal dishes. The ambiance is warm and inviting, perfect for a casual meal with friends or a romantic dinner with a loved one. Whether you're craving a light salad or a hearty entree, Summer House has something for everyone. Come and enjoy the flavors of summer all year round at this hidden gem in Orlando.

Bloomingdale's is a renowned department store located on Millenia Boulevard in Orlando, Florida. This iconic institution offers a wide range of high-end clothing, furniture, home goods, and shoes for discerning shoppers. With its elegant displays and top-notch customer service, Bloomingdale's is a go-to destination for those seeking luxury and style in their shopping experience. Whether you're looking for the latest fashion trends or upscale home decor, Bloomingdale's has something for everyone.

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.

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.

Barbados Golf View Villa is a spacious and relaxing lodging located at 3046 Barbados Lane in Haines City, Florida. This family-friendly retreat is perfect for those looking to escape the hustle and bustle of everyday life and enjoy some quality time together. The villa features 4 bedrooms and 3 bathrooms, as well as a private pool and game room for added entertainment. Golf enthusiasts will love the proximity to Southern Dunes Golf & Country Club, as well as other nearby golf courses. For those looking for theme park fun, Walt Disney World and Universal Studios are just a short drive away. Other nearby attractions include ICON Park, SeaWorld Orlando, and downtown Orlando.

Watersong Villa Rental is a luxurious lodging institution located at 548 Orange Cosmos Boulevard in Davenport, Florida, United States. With accommodation for up to 12 guests, this villa offers every possible amenity in a luxury gated development surrounded by lakes, forest, and wildlife. Just a 25-minute drive to Disney World, Watersong is perfectly situated for exploring the wealth of attractions that Orlando has to offer, including Universal Studios, Seaworld, Legoland, golf courses, and top-class shopping. The villa has received rave reviews from guests who have enjoyed the spacious layout, comfortable bedrooms, heated pool, and jacuzzi. The hosts, Richard and Nichola, are dedicated and helpful, ensuring a memorable and relaxing stay. Watersong Resort is a prestigious, gated community of luxury holiday villas nestled in a peaceful conservation site, offering the perfect retreat and base for your Florida vacation.

328 South is a trendy and stylish clothing and shoe store located in the heart of Orlando, Florida. Offering a wide selection of the latest fashion trends and footwear, this store is a must-visit for those looking to update their wardrobe. With a prime location on South Orange Blossom Trail, 328 South is a go-to destination for fashion-forward shoppers in the area. Whether you're looking for the perfect outfit for a night out or just want to add some new pieces to your closet, 328 South has you covered. Visit us today and discover your new favorite fashion finds!

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 9271 South John Young Parkway in Orlando, Florida, United States, Orange Lake Resort is a premier lodging destination that offers a unique vacation experience for families. By joining our Club, guests can enjoy more frequent vacations, create lasting traditions, and make unforgettable memories. Our partnership with IHG® and leading external exchange companies allows our members access to thousands of exciting destinations worldwide. If you're looking for a fun, rewarding career, Holiday Inn Club Vacations has open opportunities for you to explore. Founded by Kemmons Wilson, the Holiday Inn® brand has been dedicated to improving vacation experiences for families for decades.

Flutur Vacation Properties - Tuscana is a luxurious resort located at 1371 Tuscan Terrace in Davenport, Florida. This privately owned condo is professionally managed by Central Florida Holiday Homes and was completely renovated with all new furnishings in 2022. The gated resort features a zero entry pool, hot tub, and kiddie splash area, all heated during the winter months. Surrounded by lush landscaping and palm trees, the resort backs onto a beautiful conservation area and is close to world-class golf courses. Just minutes away from Disney Parks and conveniently located near shopping plazas and restaurants, Tuscana Resort offers a peaceful and relaxing atmosphere for families and business travelers alike. With amenities such as a fitness center, playground, and free parking and WiFi, guests can enjoy a comfortable stay with no additional resort fees. Whether you're looking to explore the Orlando area or relax by the pool, Tuscana Resort has everything you need for an amazing experience.

Keyvilla - The Disney Retreat is a luxurious vacation rental located at 2179 Royal Ridge Drive in Davenport, Florida, just minutes away from the magical world of Disney. This stunning property offers guests a unique and unforgettable experience, with spacious accommodations, top-of-the-line amenities, and a prime location near all the excitement of Orlando's famous theme parks. Whether you're looking for a relaxing getaway with family or a fun-filled adventure with friends, Keyvilla - The Disney Retreat has everything you need for a truly magical vacation. Book your stay today and make memories that will last a lifetime!