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Win your way to Disney World, Orlando, Disneyland or a Disney Cruise with these sweepstakes

Win Your Way to Disney World Sweepstakes

Win your way to Disney World

Win your way to Orlando Disney World, Disneyland or a Disney Cruise with these sweepstakes.  My family and I have won numerous Disney travel sweepstakes over the last several year just by persistence.  We’ve won the Disney Dream Job, an all expenses paid Adventures by Disney trip to China and we won a couple of Disney World sweepstakes before moving here in 2014.  Enter as frequently as the rules allow.

The easiest way to keep track is to bookmark this page and visit daily.  I’ll update the list frequently to eliminate old sweepstakes and add new ones.  I don’t include sweepstakes that offer small prizes.  I’ll only list the ones that provide the best prizes, most of which include free travel.

Tips for winning:

  1. Enter as frequently as the rules apply.  If the contest allows one entry per day, be sure to enter each day.  If it limits you to one entry per person or email, try entering your spouse as well.
  2. Be sure to opt OUT of any extra email options to reduce spam.  They usually ask you if you want to receive emails from their sponsors, don’t subscribe or your email will be filled with responses.  It doesn’t affect your opportunity to win either way.
  3. Use the right tools. Who wants to type their name and address over and over and over. You’ll probably end up with carpal tunnel syndrome before you win a sweepstakes! Use an autofill program to do the work for you. Enter your data once and save it, then just click autofill and it fills in the form automatically. Google offers a free autofill function in its Google toolbar application. I use Norton Antivirus on my home computer and it has an autofiller included as well. Some browsers have this ability built-in. If you come across a form that won’t allow autofill, just take a moment to type in the information.
  4. Enter the contests that require effort. The Dream Job contest in 2007 that afforded me an opportunity to play pirate at Disneyland required making a 45 second video.
Disneyland Pirate Bootstrapper

My daughter won the Adventures by Disney trip to China by embellishing some Flat Stanley artwork and writing an essay. You may find contests that ask for photography, an essay, artwork or a video. “But I’m not that creative” you say. You’ll never win if you don’t try! I believe there are far fewer entries into contests that require effort, which increases your opportunity to be a winner.

Be aware that you are responsible for the taxes on the trip(s) you win each year!

Updated 10/20/2014

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Win Your Way to Disney World Sweepstakes

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  1. Thanks for this information Kenny. I am 1 step closer to winning a disney cruise! I was close as a monthly winner for the motherhood snot easy contest. I get a year supply of boogie wipes and am entered into the grand prise drawing. Keeping our fingers crossed until May. Thanks again.

  2. I’m interested in how the “Haunt your Disney Side” prizes will work -specifically spending the night in the castle followed by breakfast at Cinderella’s royal table. The castle will be closed for refurbishments during the time you have to take your prize winning vacation– “The Grand Prize travel must occur on Sponsor-specified dates, and completed between January 19, 2015 and February 21, 2015, subject to availability”. But the castle will be closed Jan 5- Mar 6. Just curious :)

  3. I won a trip to Orlando a couple years ago through Valassis, a coupon company. People do win!! I am looking forward to my next big win !!

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