*UPDATED* Disney Vacation Sweepstakes List for May 2019

You can’t win if you don’t enter!  Here are some Disney vacations sweepstakes (legitimate ones – not scammy ones) that you can enter this month.

 There are scam Disney vacation sweepstakes circulating on Facebook again.  Please read my post on how to spot a fake so you’re not sharing the scam ones and contributing to the problem!  (But if the entries require you to “like, comment and share” – it’s fake!!) 

Here are the real sweepstakes – post has been recently update and expired sweepstakes crossed out:

Anaheim Star Wars Quest Giveaway

The Anaheim Majestic Garden Hotel is giving away Four (4) 2-day Park Hopper® Tickets for Disneyland® Park and Disney California Adventure® ParkPremium room for 3 nights, Complimentary Garden Court Bistro buffet breakfast for 4 each morning, $200 dinner credit at the NEW Hanagi Japanese Restaurant (scheduled to open May 2019), Star Wars goody basket, and Dream Machine Daily Shuttle to/from Disneyland® Park.

Enter ONCE by 5/7/2019.

Omaze Stay in the Cinderella Castle Sweepstakes

Win a Grand Prize of 2-night trip for 4 people to Orlando, includes airfare, 1-night accommodation in the Cinderella Castle Suite and 1-night in a 4 star hotel, eight 1-Day tickets to Walt Disney World with Park Hopper option, VIP tour guide and dinner at Narcoosee’s Restaurant on the Seven Seas Lagoon.

I used to not include these sweepstakes from Omaze because you have to make a charitable donation to enter.  BUT I just learned how to enter for FREE!  Use the link entitled “Alternate Method of Entry”, which is found at the end of the “Stuff Our Lawyers Want You To Know” section at the bottom of this page.

One entry per person, with bonus entries for charitable donations.  Enter thru 5/16/19. 


Classic Travel Connection is giving away a 3 – night, 4 -day stay at the Walt Disney World Resort for 4 people valued at $3600

The vacation will include the following:

-Accommodations for 3 nights at a Walt Disney World Moderate Level Resort
-4-Day Park Tickets for 4 people for up to 10 days
-Disney Dining Plan
-Admission for 4 guests to the ESPN Wide World of Sports Complex and 4 admissions to either Disney’s Fantasia Gardens Miniature Golf Course or Disney’s Winter Summerland Miniature Golf Course for (1) 18 hole round of miniature golf.

Fill out the form here to enter by 5/22/2019.

Welch’s® Fruit Snacks LEGOLAND® Sweepstakes

Yes, I know LEGOLAND is not Disney.  But winning a trip to LEGOLAND would get you CLOSE to Disney!

Welch’s® Fruit Snacks is excited to partner with LEGOLAND® Resorts to send a family of four to their choice of either LEGOLAND® California or LEGOLAND® Florida! Enjoy more than 50 themed LEGO attractions, with kid-friendly rides and shows galore. The grand prize includes air transportation, ground transportation, a two-night stay at the resort, and admission tickets to the park for all four guests.

Click HERE to enter for your chance to win the grand prize. Good luck!

Giveaway ends 5/30/2019.


Disney Springs Resort Area Hotel Stay Giveaway  (ongoing monthly)

New month = NEW chance to win!! Enter the Disney Springs Resort Area Hotels Sweepstakes for a chance to win a FREE Hotel Stay at One of their 7 Hotels in Orlando, FL! Prize includes 3 day, 2 night accommodations at one of the Disney Springs Resort Area Hotels and Complimentary transportation to all Disney Theme Parks. By entering you agree to join their email list. A New prize package will be given away each month from everyone on the email list. Only valid email addresses count as entries.

Only one email per person may enter. Final cut-off is the last day of each month at 11:59 PM EST

Popsugar Must Have Disney’s Aladdin Sweepstakes

This isn’t a true Disney Vacation sweepstakes but the grand prize is a $2,500 VISA gift card which would pay for a hefty chunk of a Disney vacation!

Five hundred (500) confirmed First Prize winners will each receive one (1) POPSUGAR Must Have Box featuring Disney’s Aladdin, each with an approximate value of one hundred and ten U.S. dollars and ninety-five cents ($110.95 USD). Exact contents of the box to be determined by Sponsor in its sole discretion. One (1) additional confirmed Grand Prize winner will receive: (a) one (1) POPSUGAR Must Have Box featuring Disney’s Aladdin, with an approximate value of one hundred and ten U.S. dollars and ninety-five cents ($110.95 USD) (exact contents of the box to be determined by Sponsor in its sole discretion); and (b) one or more Visa® gift card(s) with a total value of two thousand five hundred dollars ($2,500 USD)

Enter Once by 6/3/2019.


Disney’s Riviera Resort Sweepstakes

Enter this Disney Riviera Resort Trip Sweepstakes for a chance to win a stay at the newest Disney Resort projected to open in Fall 2019 —Disney’s Riviera Resort!

The grand prize winner will win a five day package for up to seven guests ($22,252 value) to check out the BRAND NEW resort!!


  • Accommodations in a Two-Bedroom Villa at Disney’s Riviera Resort
  • 3-Day Walt Disney World Theme Park Tickets with Park Hopper® Option
  • Airfare if the winner lives more than 250 miles away from Walt Disney World Resort

Fill out the short form by June 15th to get your one-time entry in. You can watch videos to earn additional entries.

Enter by 6/15/19!

Win an Orlando Family Vacation Sweepstakes

Win a Grand Prize of a 4-night trip for 4 people to Orlando, includes airfare, rental car, hotel accommodations and 8 single day tickets to winner’s choice of Walt Disney World, Universal Orlando or SeaWorld Orlando.

One entry per person per day. Enter by 6/27/19. 

Adventure 4 the Whole Family

Enter the Laughing Cow Disney Adventure Sweepstakes to win an Adventures by Disney vacation package worth up to $32,000! Winner gets to choose from one of five Disney adventures!  After you register and play for instant win prizes, scroll to the bottom of the page and click where it says how to obtain a bonus entry without making a purchase.

Daily entry allowed here thru 8/31/2019!

Wyndham “Key to Wyn” Sweepstakes

Enter this Wyndham ‘Key to Wyn’ Sweepstakes through December 31, 2019 and you could win the weekly prize! Each week through December 31st, one winner (52 total) will score 45,000 Wyndham Rewards Points to use on a future stay at one of 25,000+ hotels!

While not specifically a Disney sweepstakes, there are TWO Wyndham Hotels in Disney Springs! 

Enter weekly ALL YEAR!  One prize per week in 2019!


The sweepstakes on this list are legitimate Disney sweepstakes on official websites.  Be wary of scam giveaways!  Disney will never give away a vacation via a Facebook page.  Can I repeat that?  Disney will NEVER GIVE AWAY A VACATION ON A FACEBOOK PAGE!  They may advertise on their verified Facebook page but the link will take you to a page that is part of the Disney.com site.  And you know it’s a Disney vacation sweepstakes because you will have to login with (or create) your Disney website account.  (If you’ve taken a Disney trip then you already have a Disney account – use that login).  Other companies, like Redbook Magazine for example, may giveaway a Disney vacation also, but it will be clear what company is sponsoring the sweepstakes and the sweepstakes will be hosted on their legitimate website.

Just in case the previous paragraph was unclear, I created a post, complete with nifty pictures to determine if a Disney sweepstakes is real or fake.  You can see that here.

Print Friendly, PDF & Email