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. I really want to go to Hawaii because it been my dream sence i was a kid and till this day it is i love the beaches and wildlife i would love to live up to my dreams one day

    1. I do hope you get to go one day.It is a beautiful and magical place. It was our dream too and it came true! It took us a long, long time, but it happened. Create a plan – start a Hawaii savings fund – even small amounts add up if you give it enough time. Put money somewhere that is not easily accessible. An account with NO debit card attached :0)

  2. Please pick us!!! We have never been on vacation. It’s me my husband and our three kids. These kids deserve a vacation without having parents on edge or worrying. They deserve everything good in this world. I’d be forever grateful.

  3. Thank you so much for these amazing getaways! You do a great job! Me and my girlfriend have been living long distance for a while now so we look forward to a dream trip to Hawaii. Cheers!

  4. I would love to go to Hawaii with my Husband. With a little baby and an even bigger stress load at work, he deserves a break. Sometimes all you need is peace and quiet, time with your loving family and a perfect environment to escape and reset!

    1. AMEN! If only everyone could get their dream trip to Hawaii.

      Do hope you can go one day. Our best day in Hawaii is just sitting on the beach. Doesn’t cost a thing :0)

  5. The end of this month, my best friend and I are going to HAWAIIIII~ for a week trip and we have been planning this since 2 years ago now. Been on and off about it because its totally out of our(my) comfort zone. Seeing your Hawaii videos, especially this one, made me feel a lot better about going and my excitement is through the roof now.
    Looking forward to making memories now. Thanks!

  6. Would love to take my son to Hawaii. We’ve never been on vacation really. Could never afford it and he’s now 17. This would be a chance of a lifetime and working 2 jobs just to pay rent and bills no money left for luxuries like a vacation.

  7. Thank you so much for posting these! Is there any way to call out the new additions since last posting? I keep forgetting which ones I’ve already entered and I don’t want to mess up my chances entering again.

  8. I really want to go to Hawaii because me and my family don’t have money like that and I’m really hoping I win and hope you see this

  9. Thank you for the great information you continually offer! I have posted here a few times and can’t seem to find where your response to me can be found. I need to book eight people from Sacramento to Maui June 29 and returning July 6th. My question is should I wait for Southwest or book now while flights are available? Roundtrip seems to be hovering at about $1,100. per person (gasp!). Would greatly appreciate your advice. Thank you in advance, Jeanne

    1. Hi Jeanne.

      We did receive this comment and the one from yesterday, but there were none before that.

      Assuming that Southwest does announce, it is highly unlikely that fares at end of June will be discounted. Discounts will probably be from mid-August on.

      You’re dates are among the most expensive of the year. We find nonstop on Alaska at $817 for your dates. Not horrible, and do keep in mind that non-stop flights could easily become sold out on those Saturdays.


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