Win A Free Trip To Hawaii Sweepstakes

Free Trip to Hawaii Travel Sweepstakes For May 2022

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

JTV Getaway to Maui

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.

Hawaiian Bros. Sweepstakes

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.

Hawaii $50,000 Sweepstakes

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.

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721 thoughts on “Free Trip to Hawaii Travel Sweepstakes For May 2022”

  1. Greetings! Our whole family is planning a Thanksgiving trip this year to beautiful Hawaii! But me and my Fiancé are both working daily, but won’t be able to afford to join them without a lil’ blessing our way. This would be a great opportunity to get to know my new family. Stay healthy.

    1
  2. there was a Hawaii flight that once ditched near a ship mid ocean in the fifties. Pan am flight 6.
    simpleflying.com/pan-am-boeing-377-fatality-free-ditching-1956/

    fyi

  3. Wow if something like this would happen for me man it was hr some divine plan. Think lije this rarely happens even tho I live out here in vegas. I would be thankful and stund. Thanks for the opportunity:)

  4. Please consider my husband and I. Our middle daughter lives in Kauai and after 7 years of asking us to see her beloved Kauai, following a cancer diagnosis last year, I agreed. Surgery got it all. Thank God. I can’t go back on my word to her now. I would only need the flight as I will stay with her. Thank You for creating more flights.

  5. I don’t know that anyone who wouldn’t be happy a win a trip to Hawaii. I’ll be 89 in this month and that would make a very good birthday present. I’m sure that are a lot who deserve a good trip. So I hope the one who really deserves this trip will win.

    3
  6. please consider me and my wife who i been marry to for 21 years my wife had a kidney transplant last year and it would nice to see her enjoy life once again thank you so much and God blessed

  7. Aloha, I would love to surprise my caregiver husband with this trip! Please consider us as We are getting ready to celebrate our 25 wedding anniversary and would love to show him how much I appreciate and love him. We have always dreamed of going to Hawaii especially Pearl Harbor this would be amazing! Mahalo!!

  8. We had moved from Oahu in 2011. We have thrived in the mainland despite the blessings we needed from her family. However, my wife has been homesick for quite some time now. Although I have a job, and she does too, it just isn’t enough for us to save to make that trip back home for a visit. I know that she has been strong for this long to function with society away from what she had know all her life. But with God by our side I am positive that he will make it happen if it is his will.

  9. Hello there,

    Please consider me and my future husband for this trip. We are getting married on July 16th in Hampton Va. This would be the perfect honeymoon for us. Thank you for the opportunity and consideration!

    Thanks, Paris T

  10. Greetings,
    I have never been to any of the Hawaiian Islands and I am hopefull to win an opportunity to see the Island and experience the people food and culture. This would be something really diffarent.

    1
  11. This would be a dream one true to win not only for me but my friend Mary who suffered a terrible accident . She fell off her patio 3 stories down onto cement. Fortunately she lived thru it. But still has to battle everyday with the injuries she’ll have for life. It would be a true miracle if I could win this for us. Thank you Lisa Gallina.

  12. I would love to take my wife to Hawaii, she is a nurse and is one of the most caring and compassionate people I have ever met and touches so many lives in her work. This would be an amazing surprise for her and a dream come true, she has never seen the Pacific Ocean much less had a chance to swim in it. Thank you for the opportunity.

    2
  13. Please let me win a trip to Hawaii. I never been there before and can’t afford to go there. Thanks for the opportunity.

    1
  14. Hawaii is a bucket list trip my papi was planning to send me on. He had a timeshare there but he passed away a little over a year ago. When & if I ever make it, it won’t be just for me now but for him too.

    1. I never been to Hawaii I wish I can win a free trip to see Hawaii I only see pictures of Hawaii on tv and magazines but I have never seen Hawaii in person I never ever been to Hawaii I wish I could win a trip to see Hawaii

      2
  15. Please do not print expired sweepstakes/contests. Our first impression is “WOW! What a great opportunity! Followed by “Rats!” as we then notice it’s finished–in some cases, two months ago. Thanks for your consideration.

    1. Hi Don.

      We don’t publish (print as you said) expired Hawaii sweepstakes. But posts we’ve written previously remain available. There will be an update to that post coming shortly. Thanks for your comments.

      Aloha.

  16. When I got my first promotion to management we celebrated with a trip to Hawaii. The snorkeling was amazing. We have always wanted to return but putting 2 kids through college was more important. We wold love to win a free vacation to Hawaii as it could be our last family vacation.

  17. I love Hawaii, I was able to visit 18 years ago and have thought about going back ever since.
    There is just a feeling about Hawaii, serene and peaceful.
    I want to hike to a waterfall and swim in the water below.
    I want to eat all the wonderful fruit and snorkel in the
    beautiful waters.

  18. This would be a dream come true. I always dreamed of getting married in Hawaii. My boyfriend and I are talking about our future wedding in 2023 in Hawaii. This would be the best gift ever. Thank you sooo much

  19. Hawaii has been on my bucket list for years. The volcano calls me. The tropical islands call me. I long to explore the gorgeous, magical islands and understand the deep history.

  20. My fellow friends, My wife and I desire a trip to Hawaii. Of course it is a beautiful place to visit. My grandest wish is to take my wife there for the first time, her and I are both seniors and I feel that we might not ever get this opportunity in our lifetime to go. Our income will not allow us to take such marvelous trip ever. if you can grant us this wish we would be extremely grateful. Thank you for your time. Joe and Maria

  21. Hi,
    We are traveling to Maui from Las Vegas on April 6th and staying for a week. Are there any flight restrictions still in effect or is there anything we need to do before going to the airport. Thank you so much for any information you can give us.

    1
    1. Rick/Rene,

      I think the only thing remaining are masks at airports and on aircraft.

      Hopefully, that changes before your flight and it becomes a matter of choice.

      2
  22. My dad is from the beautiful place, Hawaii. He grew up there and left but his family stayed. I would love to see them, I miss them very much. I wish we could we live closer to them. A trip to Hawaii would be great to see my family, and travel the islands and see the natural beauties.

  23. BOE,

    I entered in all sweepstakes except for the NBC Young Rock Honolulu Sweepstakes.

    BTW, I also entered the 2022 San Diego Giving Back Raffle today benefiting Ronald McDonald House Charities® of San Diego. I enter this one every year – it’s not free. The Grand Prize this year is a mansion in San Diego or you can take cash (up to $3,000,000). Tons of other high-end prizes.

    2
  24. I lived in Aina Haiba.
    Loved L o v e d Hawaii!
    Miss it to my core…
    Now I’m 69, and ready to come Home! To my O’hana…
    Was an investment banker – Earlier worked for Chamber of Commerce.. lovely world…
    Anyway ~ I’m coming home!
    I’m educated/talented… and heart-sick…
    🌈🌈🏝

  25. I feel like the universe brought me to this website and I would love the opportunity to explore such the beauty of Mother Nature at her finest. Please allow me to embrace my path! Thank you! Mahalo

    2
  26. My mother will turning 90 and this will
    be a dream come true. My husband is having serious health issues but God is a healer!! This trip will mean the world to us and always thank God for his blessings and we will cherish the moments plenty together and bless those who are also trying to win.

    4
  27. My son is graduating this year form high school me and my husband work very hard but not enough to go to Hawaii I would love to be able to take him to Hawaii for a graduation present he’s a great kid that works hard in school 😁

    3
  28. Thank you and I wish the best of luck to all those who entered. Everything sounds wonderful and someone will enjoy a fantastic trip.

    3
  29. I would give anything if I could have a chance to win a trip back to kauai Hawaii for am about too turn seventy seven this coming week as of today I”ve spent my birthday there ttwo years ago and I really hated to leave ALOHA

  30. My dream yo see hawaii. I’m single mom took care of my 2 kids. Now I’m 64 & want see if I could get on section 8 or hud out there.I live in Denver CO have COPD pretty bad. Denver has the dirty air out of all the states.Hawaii would be really good for me and their lung institution too. I just want be able to get better where I don’t have to wear oxygen any more. I know some friends has moved there and their not even sick. My dream is 2 go 2 Hawaii for my dream and my health. Thank u Debi

    1

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