As of January 3, 2020, there are more new contests offering chances to win a free trip to Hawaii. Enter these Hawaii sweepstakes now and perhaps you’ll be one of the many lucky people vacationing in the islands for free this year. With one contest expiring tomorrow, don’t delay!
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.
January Win A Free Trip to Hawaii Sweepstakes
Billabong Hawaii House Sweepstakes (New)
Grand prize: Five day trip for two to Oahu. Includes airfare and accommodations.
Enter by: January 31, 2020.
Open to: Residents of the US age 18 and over.
Body Glove – Hawaii Sweepstakes (New)
Grand prize: Four day trip for two to Oahu. Includes airfare and accommodations.
Enter by: January 16, 2020.
Open to: Residents of the US age 18 and over.
Hardwood to Hawaii Sweepstakes (New – Starts 1/5/20)
Grand prize: Four day trip for two to Oahu. Includes airfare and accommodations.
Enter by: June 30, 2020.
Open to: Legal residents of California whose primary residence is within a 150 mile radius of LA.
Grand prize: Eleven day trip for two to Maui. Includes airfare and accommodations.
Enter by: July 31, 2020.
Open to: Residents of the US and Canada (except Quebec) age 21 and over.
Grand prize: Six day trip for two to Kauai. Includes airfare and accommodations.
Enter by: January 4, 2020.
Open to: Residents of the US age 18 and over.
Tropical Honeymoon on Maui Sweepstakes
Grand prize: Six day (five night) stay on Maui. Includes accommodations only.
Enter by: January 20, 2020.
Open to: Residents of the US age 18 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 January 3, 2020.
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Tracy says
Getting to go to Hawaii is the number one item on my bucket list!! I would be so so grateful!
Thank you,
Tracy D
Mildred R. says
I went to Kauai 2 times on my Birthday Oct, 15th and enjoyed everything about, it and also went to Smiths Garden Luau 2 times and had a wonderful time , I would do it again. I would like to go to Oahu to Pearl Harbor. My Dad was in ww ll and was there in Pearl Harbor. Thank you Mildred R.
Susan T. says
Thanks for offering a chance. May I win one of these someday! Fingers crossed.
Leili says
I would love to go to hawaii
Sandra D says
Sandra D- Never been to Hawaii! These trips sounds amazing! My husband and I are celebrating our 1 year anniversary next weekend : ) Would love a trip before kids come in the picture!
Breanna says
Entered every single contest on here. Would absolutely love to win one of them for our honeymoon after our wedding on June 13th of this year!
Darren R. says
I want to win this contest. I am a disabled veteran that is paralyzed on my right side from a tramatic brain injury. My wife and I would love win this trip. It will be the trio of a lifetime.
Janet K. says
AMy Heart was left in Hawaii when my husband went to paradise on Oahu for our Honeymoon June 1991! My dream is to go back. The Hawaiian experiences are none other! The Best in the world of paradise places! Thank You, Janet K.
Lashayla A says
I’m manifesting that I win one of these trips for two this year!!! Come on universe!! I believe in you! 🙂
Janet K. says
My Heart was left in Hawaii when my husband went to paradise on Oahu for our Honeymoon June 1991! My dream is to go back. The Hawaiian experiences are none other! The Best in the world of paradise places! Thank You, Janet K.
Amanda P says
I would really love to win a trip to Oahu. My daughter’s fiancé is stationed there and we have been wanting to visit him, but it is hard to come up with the funds to go see him. We would greatly appreciate it!
Pattie C says
Thank you 😊
Laurie J says
Thank you for this opportunity!
Carole C. says
I really would love to go to Maui. I have danced for 25 years with a Hula group in Canada. We loved to entertain shut ins and seniors at Care Homes. I still dance and entertain at Care Homes when I can, but have a shoulder injury so am not able to dance at the present time. I love the attitude of most Hawaiians…they do follow the spirit of Aloha, as did our dance group (not a Halau as we did not have a Kuma Hula, although our teacher took some Hula lessons in Hawaii). Going to Maui would be a dream come true. Mahalo for allowing Canadians to enter this contest
Beat of Hawaii says
Hi Carole.
Good luck!
Aloha.
Stan says
We want to go to Oahu
Tamara H says
Please
Chochanik O. says
Its our 21st anniversary on January 17th never been on a trip alone it will be a great opportunity for us to take a break from our busy schedule and just spend sometime alone. Hawaii was always on the bucket list hopefully I’m crossing fingers.
Shawn F. says
I went to Hawaii when I was in 8th grade. My husband and I have tried to save up to go for the past 27 years of marriage. My disability and my youngest daughter’s disability made it impossible to save up to return. I’ve wanted to go for 38 years. We never had a honeymoon; this was always our dream. Having three kids forced us to make choices and they always came first. Would love a trip to Hawaii. My husband and I have never had a trip alone since we had children 22 years ago.