Time to try your luck again! Enter these five Hawaii travel sweepstakes today, and perhaps you’ll be one of the lucky people vacationing in the islands on a free Hawaii vacation in 2022. Don’t delay as one contest just ended!
Beat of Hawaii has no affiliation with any of these travel sweepstakes, including who wins. So have fun, and let us know if you’re entering, and especially if you are the next lucky prize winner! It’s happened before where one of our Beat of Hawaii readers was the grand prize winner. You may be the next potential winner in a random drawing! So get going on your next Hawaii vacation with your spouse, siblings, friends, or other immediate family.
How to enter. Click on the title of each sweepstake/contest below to visit contest sites and complete entry forms. No purchase is needed. Some contests have just one winner, while others have weekly prize winners. Usually an alternate winner is chosen in case the grand price winner can’t be reached following the entry period. For contests with weekly winners, be sure to check back frequently. 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 their contact information when entering to win a free trip to Hawaii. That way, they can avoid potential spam in their regular mailbox.
Free Trip to Hawaii Travel Sweepstakes For May 2022
Grand prize: Five-day trip for two to Maui, including airfare and accommodations.
Enter by: May 13, 2022.
Open to: Residents of the U.S. age 21 and over.
The Lesser Evil Jurassic World Dominion Sweepstakes
Grand prize: Seven-day trip for two to Honolulu Hawaii, including airfare, accommodations and $500.
Enter by: July 31, 2022.
Open to: Residents of the U.S. age 18 and over.
Roxy Win A Trip to Waikiki Sweepstakes
Grand prize: Seven-day trip for two to Honolulu Hawaii, including airfare and accommodations.
Enter by: September 30, 2022.
Open to: Residents of the U.S. and Canada (except Quebec) age 18 and over.
Grand prize: Trip for two to Hawaii, including airfare, accommodations and excursions.
Entry Tip: Link goes to the rules. Read Rule #4 for more details on how to enter.
Enter by: June 6, 2022.
Open to: Residents of the U.S. and Canada (except Quebec) age 18 and over.
Grand prize: $10,000 cash. Enough for the Hawaii vacation of your dreams!.
Enter by: March 31, 2023.
Open to: Residents of the U.S.
Notes: As a reminder to participants, read all the official rules, including the sweepstakes period, since each contest is quite different. Also, while some of these include other prizes, we have only listed the free Hawaii vacations. Prizes vary from cash and expenses or fees to airline tickets and accommodations, to travel vouchers, plus additional compensation, based on the decisions of the sponsor. No purchase necessary to win. Contests are void where prohibited and are open to legal residents of the United States, its possessions, and sometimes Canada (depending on the contest, local laws and regulations). Check rules for entrants eligibility and acceptance and notification rules, as contests aren’t open to employees of sponsors, promotional agencies, and their subsidiaries and related sister sites. An affidavit of eligibility and a publicity release is generally required. Odds of winning vary by contest. Also, check for minimum years of age as well as the last date and time of entry of the promotion period. Some travel sweepstakes limit the total number of eligible entries per person. Determinations are at the sponsor’s sole discretion.
Whether you are traveling from New York, Orlando, Houston, Dallas, Baltimore, Pittsburgh, Washington, Alaska, Portland, or California, there’s nothing like a free trip to Hawaii! Just let us know how it goes and if you are the next lucky Beat of Hawaii winner.
Post Updated May 8, 2022.
Disclosure: We receive a small commission on purchases from some of the links on Beat of Hawaii. These links cost you nothing and provide income necessary to offer our website to you. Mahalo! Privacy Policy and Disclosures.
Don B says
10-18-21 Please let us know if you do NOT have HI contests for October. The only ones listed are September and before. Thanks.
Beat of Hawaii says
Hi Don.
We will be updating with new contests shortly.
Aloha.
Carol B says
I like to hear what is going on in Hawaii
Sandra c says
Hawaii was the best vacation I ever had. After so many trials in life the two week I’ve spent there I was truly happy how can you not be form the time the plane touched down I felt my spirit renewed in every mountain and flower I saw I felt alive again the Beauty of the island of Honolulu was so amazing I can wait to go back again please allow me this chance thank you for this opportunity
Cincanada says
How I wish a contest would come that included Canada. 🙂
Sandy R says
The main reason I would love to win is to take flowers to my mom and dads gravesite. Cant afford to pay the airfare and stay. I haven’t been home for over 10 years I would love nothing more then to see my home again. Please help me get there… Mahalo
Carol V says
I love all of these different flavors.
Vik says
Alohaaa!!! I’m so happy to enter this is a dream come true thanks for all of this! Also it’s actually a dream come true if it happens because I just saw a dream of me going to Hawaii and I really just can’t get it out of my head!! Love uuu !!
Venus D. says
To whom it may concern,
My name is Venus Dyson, I would love to win this trip because my husband and I just celebrated our 5th wedding anniversary on July 9th, 2021, and we have not been able to have a honeymoon yet. You see when we got married we only had enough money for the wedding. We could not afford to go on a honeymoon. Because to the Covid-19 we have not been able to travel. I would love to be able to surprise my husband and take him on our honeymoon after all of this time. Thank you for your time and may God continue to bless you!
Sincerely,
Venus L. Dyson
Michelle B says
Thank you for the opportunity to apply to sweepstakes to visit Hawaii. My husband and I will be celebrating our 25th anniversary May 17, 2022. We cannot afford the trip of our dreams but hope that we have an excellent chance of winning. We really need a vacation and I really want to make our 25th anniversary special and memorable.
Thanks Again for this opportunity,
Michelle B
Beat of Hawaii says
Hi Michelle.
Good luck! There will be more contests posted in the next few days so stay tuned for that too.
Aloha.
Michelle says
Thank you 🙏 I really want try take my family on a vacation… we have never been anywhere.
LEAH J says
Looking forward to some Aloha time!
Anahi A says
Please we need another vacation thanks!
DEBORAH L says
thanks
Abe S says
As a local boy who has not returned home since 1966 and do not have enough funding, I would love to see my homeland one more time
Yolanda D says
thank you for a chance to enter and win a beautiful vacation. it has always been a dream of mine to go to such a beautiful place. have a great day!!
Janet says
We would love to win this trip What a great vacation getaway.
For years, my husband has wanted to fish the tarpon and I have wanted to experience the Hawaiian customes and “hang ten” with residence whom live there. What a great opportunity for us. After 30 years of marriage we have never been on a vacation like this. Thanks for this opportunity.
Frank J says
Was in Hawaii many years ago would love to go back
james says
Thanks for the info. I enjoy pondering the possibilities of a win
Deborah S says
Aloha🌴Hawaii🌴Mahalo
Lorraine K. says
I hope I can win a trip to Hawaii. I simply love Maui and would love to come back. The sunsets are amazing and I want to be able to see them again. Thank you and please call me for my trip.
David King says
Thanks