win hawaii vacation

Free Hawaii Sweepstakes and Contests

Enter These Sweepstakes for Your Chance to Win Free Hawaiian Vacations

Free Chances to Win a Trip to Paradise!

Would you like the chance to visit beautiful Hawaii? The 50th state gives you chances to surf big waves, relax on picturesque beaches, snorkel with exotic fish, and luxuriate in some of the most beautiful nature our planet has to offer. And these Hawaii Sweepstakes and Contests give you chances to win an unforgettable vacation for free.

Check this page regularly to find free chances to win a Hawaiian vacation. This list is updated every day, and it’s full of the best current Hawaii giveaways offered by trustworthy companies. You can also find chances to win free airfare to the Hawaii islands, free stays at beachfront resorts, and other related prizes.

Before you enter any of these giveaways, it’s a good idea to consider whether each vacation giveaway is right for you. If you are new to entering and winning sweepstakes, find out how to enter online sweepstakes like a pro to make sure you don’t make any mistakes that would affect your chances of winning.

If another type of vacation is also on your agenda, check out these sweepstakes lists:

  • 100 Great US Vacation Sweepstakes
  • International Travel Sweepstakes
  • Win a Free Cruise Sweepstakes
  • Sweepstakes to Win Disney Vacations
  • Win Free Las Vegas Vacations

And don’t forget to stop by TheBalance’s Sweepstakes Directory to find even more prize categories, like chances to win cash or instant prizes.

If you are chosen as the winner, you’ll be notified by the sweepstakes sponsors directly. You can learn more about ​what happens when you win sweepstakes and how to recognize the warning signs of sweepstakes scams.

Ready to start entering? Here are the current chances to win a free trip to Hawaii:

1. Billabong – Billabong Hawaii House Sweepstakes
Here’s your chance to win a four-night getaway for two people to Hawaii.
Entry Frequency: One time per person/email/household
End Date: January 15th, 2021
Eligibility: Open to residents of the United States (void in Rhode Island)
More Information about this Sweepstakes
Enter Sweepstakes Directly

Are you yearning for a trip to paradise? Visit TheBalance's Hawaii Sweepstakes List for legitimate chances to win free Hawaiian vacations.

Win a Tropical Trip for 4 to the Hawaiian Island of Your Choice


Enjoy a weeklong vacation on your dream Hawaiian island—choose from the Big Island, Maui, Oahu and Kauai

Score $2,000 to make the most of your trip, from surfing lessons and kayak adventures, to shopping sprees and seafood cuisine

Get flown out and put up in a 4-star hotel

Your safety and peace of mind is our top priority, so we’ll make sure this trip is scheduled when it’s safe. You’ll have until December 31, 2022 to travel.

what you’ll do

It’s time to play Choose Your Own Adventure… in Hawaii! You and your family will enjoy a weeklong getaway to the Hawaiian island of your choice. You can go big on the Big Island: Visit Hawai’i Volcanoes National Park, relax on a black-sand beach or hit up a world-class golf course. Maui more your speed? There’s an adventure waiting for you around every corner on this fan-favorite island—from surfing and kayaking, to hula lessons and luaus. Don’t forget about Oahu, home to Honolulu and the iconic Waikiki Beach, action and relaxation, plus tons of shopping and surfing hotspots! And Kauai? Kauai not! This lush green isle is paradise for hikers, nature lovers and those looking to escape the crowd. Just make your choice, and we’ve got the rest. Your flights, hotel and $2,000 cash are all on us!

No donation or payment is necessary to enter or win this sweepstakes.

who you’ll help

Headstrong provides cost-free, bureaucracy-free and stigma-free treatment for the hidden wounds of war. Working in partnership with Weill Cornell Medical College, one of the nation’s leading mental health care centers, Headstrong uses a comprehensive treatment program to help post 9/11 veterans deal with PTSD, anxiety, depression, trauma, grief, loss and anger management. With your support, Headstrong can extend their proven program to reach more veterans in need.

entry levels

Choose the amount below. No donation or payment is necessary to enter or win this sweepstakes.

250 entries to win

100 entries to win

100 entries

100 chances to win a tropical trip for 4 to the Hawaiian island of your choice

250 entries to win

250 entries

250 chances to win a tropical trip for 4 to the Hawaiian island of your choice

1,000 entries to win

1000 entries

1000 chances to win a tropical trip for 4 to the Hawaiian island of your choice

2,000 entries to win

2000 entries

2000 chances to win a tropical trip for 4 to the Hawaiian island of your choice

Hey! You may also want to…

stuff our lawyers want you to read

You (“Winner”) + 3 (“Guests”)

Sweepstakes Start Date:
October 8, 2020

Deadline to Enter:
January 14, 2021 at 11:59pm PT

Winner Announced:
On or around February 3, 2021

Approximate Retail Value:

TBD, must be booked by December 31, 2022

Hawaii, USA

Omaze, Inc. (“Sponsor”)

Designated Grantee:
Headstrong Project (“Designated Grantee”)

All donations made in connection with a fundraising campaign are paid to Charities Aid Foundation of America (“CAFA”), an IRS-recognized, U.S. public charity whose mission is to make giving internationally and domestically safe, easy and effective for U.S. donors. CAFA prequalifies each Designated Grantee as an eligible recipient of CAFA grants. At the end of each fundraising campaign, so long as the Designated Grantee continues to qualify as an eligible recipient of CAFA grants, CAFA will make a grant to the Designated Grantee of the net proceeds of the fundraising campaign.*

Prize Provider:
Omaze, Inc. (“Prize Provider”)

Grand Prize Details: Winner and 3 guests will receive roundtrip airfare and accommodations for a 7 day/6 night trip to their choice of one of the following destinations: Maui, Oahu, Kauai, or the Hawaiian big island. Winner will also receive a $2,000 USD stipend (the “Grand Prize”).

Omaze may permit Winner to receive a cash alternative prize in the amount of $6,750 (United States Dollars) in Winner’s sole discretion (the “Cash Option”). If Winner elects the Cash Option, Winner will be solely responsible for all applicable taxes.

All third party names and trademarks are the property of their respective owners.

Age to Enter: You must be at least 18 years old to win.

Ineligible Countries: Winners must not be residents of Belgium, Cuba, Iran, Iraq, Italy, North Korea, Singapore, Sudan, Syria or Thailand.

Eligibility Notes:

Guests must be of legal age of majority in his/her jurisdiction of residence (and at least 18), unless Winner is the parent / legal guardian of Guests. No individual younger than 5 years of age may be a Guest. In addition to Winner requirements (detailed below), Guests must complete and return a publicity and liability release prior to departure. If a Guests are minors, then the Winner must execute and return all required documents on behalf of such minor child. If Winner and/or Guests reside outside the country where experience will take place, Winner and/or Guests must have current, valid passports, and be able to travel to the experience location(s). If they are unable to travel to the experience location(s), they will forfeit the prize.

In certain countries, local rules and laws may restrict or prohibit the award of certain prizes or impose additional restrictions on participation. Entry is subject to all local laws. See our Sweepstakes Official Rules for more details. Employees, officers, and directors of Sponsor, Designated Grantee , or Prize Provider, and members of their immediate families and households, are not eligible to win.

Individuals may not receive more than one grand prize within the same 18 month period. Individuals may not receive more than one minor prize within the same sweepstakes.

How to Enter:
Visit to utilize any of our methods of entry. See our Sweepstakes Official Rules for more details. Odds of winning depend on the number of entries held.

Winner Confirmation Process:

Within 10 business days of campaign close, we’ll use an automated random drawing process to draw a potential winner(s) for that campaign. A confirmation process, which may include a background check, will then take place to ensure the potential winner meets the legal standards required. Winner and, if applicable, their guest(s) agree to cooperate fully with Omaze in Omaze conducting any background check(s), which includes providing information requested by Omaze including, but not limited to, full legal names and addresses. If the Prize includes meeting a celebrity, meeting a public figure, or attending a special event and any background check indicates, in Omaze’s sole discretion, that the potential winner or the potential winner’s guest(s) pose a danger to or may harm the reputation of any person or entity involved in the sweepstakes, Omaze may disqualify said winner and move on to the next randomly drawn potential winner. Pending a positive outcome of the confirmation process, an Omaze representative will notify the potential winner via email and/or phone. The potential winner must respond within the time period designated in the notification, or Omaze may move on to another randomly drawn potential winner. Before confirming a potential winner as the winner, Omaze may require the potential winner to confirm their eligibility. Once that’s done, the potential winner and guest(s) must execute and return all required documents within the time frame specified by Omaze. If you do not execute and return all required documents within the time frame specified by Omaze, you will forfeit the Prize and Omaze will move on to another randomly drawn potential winner.

Travel companions are also required to sign a liability/publicity release prior to issuance of tickets. Additionally, travel companions/guests of the winner may be subject to a background check, which may impact their ability to participate in the Prize.

NO PURCHASE, PAYMENT, OR CONTRIBUTION NECESSARY TO ENTER OR WIN. Contributing will not improve chances of winning. Void where prohibited.


At Omaze, we believe fundraising should be about impact, not percentages. Our model allows us, in partnership with Charities Aid Foundation America (we call them CAFA), to really make a difference and disrupt the way society traditionally thinks about charitable giving.

Here’s how it works: Omaze and CAFA work together to offer incredible prizes and experiences that anyone can potentially win. You don’t have to donate to enter, but if you do, your donation to CAFA is then used to make a charitable grant to a great cause, which we love. Omaze pays for everything that’s needed to run the sweepstakes, which means the only ones taking a chance are the entrants (you!)—not the Designated Grantee. The organizations can spend less time worrying about raising funds, and instead focus their energy on doing awesome work.

*Omaze also invests in securing the prizes for the typical Omaze Owned campaign, so for these, from every dollar you donate, 15 cents is used by CAFA to make a grant to the associated charity. If there are multiple charities, then grants of equal share are made to each charity. 70 cents is typically used to actually get the prize, process payments and advertise to awesome people like you (Omaze Owned campaigns require more significant marketing efforts by Omaze and do not rely (or rely to a much smaller degree) on the work and name of celebrities to help raise awareness and promote the campaign). The remaining 15 cents of your dollar goes to Omaze—it’s used to cover the cost of providing and maintaining the technology and team that makes this all happen.

The result? Causes get a guaranteed grant with no risk and no overhead or investment, our lucky winners get awesome prizes, and everyone else gets to help a great cause and spread joy!

To learn more about how we support causes in partnership with CAFA, see our Terms of Use.

YOU AND 3 GUESTS WILL: Enjoy a weeklong vacation on your dream Hawaiian island—choose from the Big Island, Maui, Oahu and Kauai Score $2,000 to make the most of your trip, from surfing lessons and kayak adventures, to shopping sprees and seafood cuisine Get flown out and put up in a 4-star hotel Your safety and peace ]]>