Ok, everyone, I know the subject line might sound unrealistic but it's true. Also just a heads up this might not work for everyone but it did for me and my wife.
October of 2018 we went on a trip to Maui Hawaii for $1500 total for 2 people.
Here is how we did it.
I saved up airline vouches by taking the later flight. I used to work for a company that had to fly me around twice a year. I needed to be at my office the next morning but they would always put me on the 5:00 pm flights and they often oversold them so I would tell the desk attendant I would take the next flight if they could give me a voucher, or sometimes they would announce they needed to pick to take a different flight because it was oversold and I would volunteer. I had $800 in-flight vouches in 18 months. This paid for our flights because we went in the offseason so we found lights for a little over $400 RT.
Ok so here is the crazy part that might not work for everyone.
I got a job at my local Marriott hotel working 1 day a week on Saturdays. This gave me an employee discount when traveling. We had to be creative on where we stayed as well. we stayed 4 nights one place and 2 nights another. The discounted rates we not available for all 6 nights we were there so we had to switch properties mid-trip. We stayed in a $500 a night resort for $99 a night and they waived the resort fee ($42 daily) because I was a fellow employee.
The Rental Car
I booked my rental car the day I got there. This was a little risky but it paid off. I don't remember exactly the price but I think it was like $128 for 4 days. So $25 a day. It would have been less but I upgraded to a jeep when I got there.
Lastly, we saved money on food because we had a fridge and requested a microwave in our room and went to the ABC marts all over Hawaii and got normal deli food and snacks but for so much less.
Let me know if you have any questions happy to help.
It was so amazing we are going back to Hawaii this year!