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Some of the biggest and best Florida villas can be found here, so you can live like an A-lister for a week or two.
When it comes to location, Kissimmee wins hands down. Not only does it offer Airboat tours that are on the headwaters of the Everglades but it’s proximity are only minutes from legendary theme parks makes this destination a big draw for families.
Many villa communities are located just 25 minutes from the entrance to Walt Disney World Resort®, with Universal Orlando Resort® and SeaWorld Parks Orlando® within easy reach too.
If a hotel-based stay is more your style, Kissimmee is home to a wide selection of close-to-everything accommodations, from luxurious resorts to value stays.
Kissimmee also offers a wealth of entertainment. It has its very own amusement park - with plenty of opportunities for shopping and dining.
For those who like to get outdoors, Kissimmee showcases the stunning, natural beauty of the sunshine state where you can enjoy zip lining over Alligators, hot air balloon rides and nature trails!
2025: 7 Nights Kissimmee & 7 Nights St. Petersburg2025: 7 Nights Kissimmee & 7 Nights St. Petersburg
2025: 7 Nights Kissimmee & 7 Nights St. Petersburg 2025: 7 Nights Kissimmee & 7 Nights St. Petersburg
- Accommodation: Fantasy World Resort, Sirata Beach Resort
- Location: Orlando, St Petersburg
- Flight: London Gatwick
- Travel: Select dates in November 2025, call for other departures Travel: Select dates in November 2025, call for other departures
- Best For: Multi Centre, Beach Holiday, Family Holiday, Twin Centre
Mobility Friendly 2025: 7 Nights Caribe Royale All-Suites & Convention Center incl. TransfersMobility Friendly 2025: 7 Nights Caribe Royale All-Suites & Convention Center incl. Transfers
Mobility Friendly 2025: 7 Nights Caribe Royale All-Suites & Convention Center incl. Transfers Mobility Friendly 2025: 7 Nights Caribe Royale All-Suites & Convention Center incl. Transfers
- Accommodation: Caribe Royale Orlando All-Suites
- Location: Kissimmee Area
- Flight: London Gatwick
- Travel: Select dates in January 2025, call for other departures Travel: Select dates in January 2025, call for other departures
- Best For: Family Holiday
Wyndham Orlando Resort & Conference Center Celebration Area Kissimmee Area Wyndham Orlando Resort & Conference Center Celebration Area
Based on 807 reviewsWyndham Orlando Resort & Conference Center Celebration Area Wyndham Orlando Resort & Conference Center Celebration Area
- 8 minutes drive to Walt Disney World
- Outdoor heated swimming pools
- Free shuttle to Orlando theme parks
- Best For: Multi Centre, Twin Centre
Caribe Royale Orlando All-Suites Kissimmee Area Caribe Royale Orlando All-Suites
Caribe Royale Orlando All-Suites Caribe Royale Orlando All-Suites
- Accessible hotel within 1.5 miles from Disney parks
- Three accessible outdoor pools and two hot tubs
- Shuttle service to Walt Disney World
- Best For: Family Holiday, Short Break
Comfort Suites Maingate East Kissimmee Area Comfort Suites Maingate East
Based on 2278 reviews
Comfort Suites Maingate East Comfort Suites Maingate East
- A Disney Good Neighbor Hotel
- Free wireless internet throughout resort
- Free daily breakfast buffet
- Best For: Family Holiday
Fantasy World Resort Kissimmee Area Fantasy World Resort
Based on 1148 reviewsFantasy World Resort Fantasy World Resort
- 2 bedroom, 2 bathroom villa accommodation
- Variety of nightly entertainment
- 2 pools, 3 hot tubs and a lazy river
- Best For: Family Holiday
Mystic Dunes Resort & Golf Club Kissimmee Area Mystic Dunes Resort & Golf Club
Based on 3654 reviewsMystic Dunes Resort & Golf Club Mystic Dunes Resort & Golf Club
- Spacious condo-style accommodation
- Tennis courts and 18-hole miniature golf course
- 4 resort pools, water slides and cabanas
- Best For: Family Holiday
Holiday Inn Club Vacations at Orange Lake Resort Kissimmee Area Holiday Inn Club Vacations at Orange Lake Resort
Based on 7432 reviewsHoliday Inn Club Vacations at Orange Lake Resort Holiday Inn Club Vacations at Orange Lake Resort
- 1 to 4 bedroom villas with fully-equipped kitchens
- Furnished patio or balcony with each room
- 3 on-site golf courses
- Best For: Family Holiday
Looking for an outdoor activity that’s a little different to the norm? Why not take in the magic of Orlando from a height as you float along the sky at sunrise? A hot air balloon ride is a truly spectacular way to celebrate yo...
Get away from the hustle and bustle of Kissimmee’s more famous attractions with a relaxing day trip to Kissimmee Prairie Preserve State Park. The adventures begin from the moment you arrive as you drive along the five mile roa...
Go back in time with a trip to Kissimmee’s Medieval Times Dinner, where you’ll find yourself magically transported to 11th century Spain. Wander around the Hall of Arms and authentic old-world cottages as you discover me...
Now and Get
Experiences
Enjoy the very best of Orlando with the FREE Ocean Explorer worth up to $440* per family. When you book your Orlando or Kissimmee holiday, you’ll receive four free experiences to some of our favourite Orlando hot spots. Witness the Outta Control Magic Comedy Dinner Show, splash out with a $20 voucher for Mall at Millenia **, explore International Drive on the I-Ride Trolley and take a ride on The Wheel at ICON Park.
*$440 saving per family of 4 or $110 saving per person **Only applicable to over 12s
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We’ve been celebrating The Sunshine State for decades! Every member of the team at Ocean Florida is committed to planning your holidays, exploring Florida, sharing stories and crafting memories. We decided to put together a fun, friendly video featuring our actual team members to show you just how passionate we are about all things Florida. Press play to see exactly why – when it comes to Florida holidays – we are the ones to know!
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Kick Back in Kissimmee
Plan your next trip to Kissimmee and enter a world full of fun and excitement. Its location in Central Florida means it's just a stone's throw away from Orlando's famous theme parks and attractions. Kissimmee offers the perfect blend of thrills, nature, and culture but lucky for you, that's not all. With plenty of dining options and great attractions, if you opt for staying in a Kissimmee Villa it will ensure you have the right base to enjoy your holiday. We're here to help you get ready for a holiday of a lifetime so let's immerse ourselves in the wonders of Kissimmee.
The Paddling Center at Shingle Creek
Start your Kissimmee holiday at the Paddling Center at Shingle Creek. Get the chance to explore the real Florida as you rent out a paddle-board, kayak, or canoe to sail along the beautiful Cypress forest. Strap up your life vest as a trained instructor follows you along your nature trail. Also, for any parties traveling with a dog they are pet-friendly!
Orlando Tree Trek Adventure Park
Get your adrenaline pumping as you swing across Orlando Tree Trek Adventure Park. Take on the 425-foot zip line as you glide through 97 different aerial challenges up in the trees. Designed for people ages 7 years old and up, the whole family can live out their Tarzan dream swinging from ropes, trapeze, and more. Just try not to look down too much!
Bok Tower Gardens
If you've never seen a singing tower before this National Landmark is for you. Bok Tower Gardens, opened in 1929 was donated by Dutch writer and humanitarian, Edward Bok. His desire was to create a place where animals and humans can be at peace. Nestled among the lush green gardens, you'll find the famous 205-foot Singing Tower, where its bell sings for 30 minutes at 1 pm and 3 pm.
Osceola Arts
Calling all performing art enthusiasts to Osceola Arts. Since 1960, this theater has been home to all things creativity and has connected people from around the world with its mesmerizing shows. Witness one of the 150 shows they showcase each year, from Broadway-style shows to children's theater, art exhibitions, and more. It's a great way to see what Central Florida has to offer.
Pioneer Village
Step into Kissimmee's past at the Pioneer Village also located in Shingle Creek. This living history museum tells the tale of the pioneers who lived in Kissimmee during the late 1800s and features authentic permanent structures for your viewing pleasure. Walk through the 160 acres of land and come across the village schoolhouse, church, and other notable buildings.
Wild Florida
Drive off on a mini adventure as you experience Wild Florida. This drive-through safari park brings you up close and personal with more than 150 exotic and wildlife animals in their natural habitats. If you ever wondered what Florida looked like 100 years ago this would be it! Not only can you delve deep into the swamps but you can experience painting with the tallest living animal on the Earth. Talk about living on the wild side!
Chocolate Kingdom
Consider dessert sorted as you venture off to the Chocolate Kingdom. Get stuck into tons of chocolaty goodness as you explore the part museum, part factory located here in Kissimmee. Learn all about how chocolate is made and the journey it takes through production on an interactive tour. You'll be led through the Cacao Tree Greenhouse, Chocolate Museum, Mystical River of Chocolate and more! Don't be surprised if you end up dreaming about it later!
Old Town
Old Town is the perfect place if you fancy a walk down memory lane. Filled with retro and vintage details, take a step into the past as you wander around this cool Kissimmee spot. Have your choice at different entertainment spots, or dress up the whole family and pretend you're in an old-school classic all for free. We're sure any parties traveling with teens are sure to love it.
Eli’s Orange World
Whether you're a lover of fruit or chocolate this place is for you. Eli's Orange World is an eye-catching fruit stand and gift shop shaped like a, you guessed it - orange! Although there are loads of different souvenirs to buy from fruit-themed products to merchandise, you can simply head there to bask in uniqueness. Make sure to get your free photo of this iconic spot.
Kissimmee Area Holidays
Kissimmee Area Holidays
Kissimmee Area Holidays
Why not take a hot air balloon to get a sky-high view of the town and the town and natural surroundings? Or have a gander at some old-school motors at Old Town Kissimmee? There’s plenty to get up to, and when you want to relax after a day at the parks, you can return to a homely villa provided by Ocean Florida. Villas are finished with everything you need for a self-catering holiday and include a private pool, so you can cool off from the sun. Each Kissimmee villa is unique, so you’ll have all the more reason to return again and again.
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