Updated as of November 6, 2019 with new contests. Enter Hawaii sweepstakes for a chance to win a free trip to Hawaii. Enter these Hawaii sweepstakes now for a chance to be one of the many lucky people who will be vacationing in the islands for free.
Who doesn’t want a free trip to Hawaii? Cheap flights to Hawaii can’t even touch winning the ultimate Hawaii sweepstakes.
Beat of Hawaii has no affiliation with any of these sweepstakes including who wins. Have fun and let us know if you’re entering, and especially if you are the next lucky winner! It’s happened before where one of our Beat of Hawaii readers had the winning entry.
As a reminder, read all the rules, since each contest is quite different. While some of these include other prizes, we have only listed the free Hawaii vacations.
How to enter. Click on the title of each sweepstakes contest below to visit contest sites and complete entry forms. No purchase needed. Also be sure to uncheck any applicable boxes if you don’t want to receive other emails from contest sponsors.
Tip. Some readers have said they use a separate email address for entering to win a free trip to Hawaii. That way they can avoid potential spam in their regular mailbox.
November Win A Free Trip to Hawaii Sweepstakes
Where Magazine Trip to Waikiki Giveaway
Grand prize: Three day trip for two to Oahu in the form of $1600 towards airfare plus accommodations and $500 gift card.
Enter by: November 30, 2019.
Open to: Legal residents of of the US age 21 and over.
Mineragua Holidays in Hawaii Sweepstakes
Grand prize: Trip for two to Oahu in the form of $2000 resort gift card for accommodations at the Turtle Bay Resort, $1800 airline gift card, $600 Visa gift card.
Enter by: November 17, 2019.
Open to: Legal residents of of the US age 18 and over.
Outrigger What’s Your Waikiki Sweepstakes
Grand prize: Trip for two to Oahu. Includes 120,000 HawaiianMiles from Hawaiian Airlines plus five nights accommodations at a choice of hotels. The miles are enough for 2-3 round trips from the west coast to any Hawaiian Island
Enter by: November 25, 2019.
Open to: Legal residents of of the US and Canada (except Quebec) age 18 and over.
HawaiianMiles & Dream Cruise Giveaway
Grand and other prizes: 1) Trip to Hawaii in the form of 250,000 HawaiianMiles from Hawaiian Airlines plus a $3,000 cruise vacation voucher. The miles are enough for 4-6 round trips from the west coast to any Hawaiian Island. 2) Trip to Hawaii in the form of 100,000 HawaiianMiles. 3) Trip to Hawaii in the form of 50,000 HawaiianMiles.
Enter by: November 30, 2019.
Open to: Legal residents of the US age 21 and over.
Grand prize: Trip for two to Maui. Includes airfare and accommodations.
Enter by: November 15, 2019.
Open to: Age 16 and over.
Perfect Days Hawaii Sweepstakes
Grand prize: Six day trip for two to Maui. Includes airfare, condo, car.
Enter by: January 31, 2020
Open to: Residents of the US and Canada (except Quebec) age 21 and over.
Updated November 6, 2019.
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Jazmine R. says
Fingers crossed. This would be a dream come true and much needed getaway for my little ones and I
Taylor H says
Me and my best friend got married on Halloween this year! We can not afford a honeymoon and this would literally be a dream come true!!!!
Julie M. says
Bucket list to go to Hawaii and my daughter graduates this year.would love to take a trip with her before her adult life begins.
Sandy R. says
This would be a dream come true for me more than anyone would know..
Nelly says
I would love to a trip to Hawaii as my honeymoon because so far i won’t have one.
Lorraine says
Thanks for offering some very inviting sweepstakes! Please, please, please choose me! Had a rough year recuperating from liver/kidney transplant. What a treat it would be to be the recipient, though being blessed with a new life is the biggest treat anyone could hope for. Thank you!
June J. says
Would live to see Hawaii and my daughter in the airforce. She has been waiting for me to come see her. Pkus our honeymoon is 2 years over due
Cindy L. says
Cindy
From dc
I would love to come here for my birthday! December 8
Nyah R. says
I never been out of my small city I’m in college this would be a great vacation for me and my daughter ❤️
MB says
Love to celebrate my husband’s retirement.
Jackie W. says
My husband is a retired wounded veteran that has no had a vacation since 2008 and I would love to take him somewhere.
Joyce M. says
I would love to win a trip to Hawaii and renew my wedding vows. We will be married 42 yrs in June 18, 2020
Esther C. says
April 18, 2020!!! Our 59th wedding anniversary!!!