You Can Always Afford a Holiday This Way

Imagine waking up whenever you want to the sounds of exotic birds and beautiful scenery. It's wonderfully warm and you decide to take a quick dip in the pool before having breakfast including tropical fruit. This was our life in Fiji. We were there for around 3 months at a time over the last couple of years. It was great. Wouldn’t it be wonderful to be able to take a holiday like that whenever you wanted? Well, you can.

Well, maybe you can.
Well, if you meet the right criteria you can.
How to do it
Here are the criteria;
You need to have income that doesn't require you to be at a fixed location.
You need your accommodation expenses where you normally live to be paid by someone else.
This is so simple, yet so powerful. You could easily do this without the above if you already have the money. But I intend to make money while on holiday. The aim is to get wealthier not just get by.
The first part requires you to have an income that is not location dependent. You could get a job that doesn't need you to be in a certain location (or some kind of work from the location where you want to be like the working holiday idea). It's easier if you're retired. I suggest everyone to aim to get to this position, even if you want to work.
The second part, if you have accommodation costs where you live you need someone to pay for it. What do I mean? If you are renting somewhere, then you would need to stop renting. If you own your own property, you would want someone to rent your property while you're away on holiday. That way you don't have the extra costs while on holiday.
Stay Longer
It works out better to stay at your holiday destination longer because it divides the costs of travelling each week. Let me explain. If your travel cost is $2000 and you stay for 1 week, then it's $2000 per week that you've spent to stay there in travel costs. It would be $400 for five and $200 for ten weeks and so on. We try to budget so that all the costs of travel are around the same or less than what we would pay at home.
Most people pay a huge amount of money for their one-week getaway. We actually are at least break even if not gaining when we take our long term excursion. This makes it a no-brainer to think whether to take that “holiday” or not. Of course, it's harder if you live somewhere where living costs are low and the holiday place is more expensive.
This strategy has helped us to travel for extensive “holidays”:
In 2001 we went to Melbourne for 6 months (including travelling back to New Zealand every few weeks).
In 2004 we lived in Guangzhou for 2 years (including travelling back to NZ for Christmases).
In 2010 we went to Zhuhai, China for 3 months.
In 2012 we lived in Brisbane for 2 years (including travelling back to NZ for Christmases and other things).
In 2015 and 2016 we went to Fiji (twice for 3 months each time).
Currently, we are in Brisbane, but planning our next move.
DISCLAIMER, we may or may not have been aware of this strategy on some or all of these so called holidays. You get to see the world while still getting wealthier. It's awesome!
Where to Aim For
Look outside the CBD in suburban areas. Or on the fringe of major tourist holiday hotspots. We are not talking about staying at 4 or 5-star resorts but in residential accommodation. You pay premium inflated prices for hotels that don't have real living facilities (like kitchens and bedrooms). Whereas in renting in the local residential market you will be competing at market rates. You need to get something furnished. That means it needs to come with beds, fridge, microwave, kitchen stuff, washing machine and so on. It might be difficult to find in peak season and some places might not have many options. But, we've found that you could pay around the same or just a bit more for furnished as you would for unfurnished.
When to Travel
If you can’t travel for long periods try taking your breaks during times when schools are in session. Because you can save so much more in travel and accommodation costs when you aren’t competing with every man and his dog (or kids in this case). We have 5 young kids, so travelling becomes much more complicated - for a start we'd have to book at least two rooms. But because we home-school them, then it easier to go whenever without waiting for school breaks.
Cheap Short-term Holiday Accommodation
If for some strange reason you can't go long-term, below are short-term and cheap accommodation ideas. We've stayed at a house right on the beach for US$30 a night, a house right across from the beach for around US$120 per week and even a house with beautiful views for just a donation. They weren't high-class swanky joints. The last thing you want on your holiday is to be hovering over the kids to make sure they don’t bring any sand or stray crabs in from the beach. You'd be surprised at what is available for very cheap outside of peak times. You just have to search outside the mainstream Google results.
We stayed at a large house right across from the beach for USD$120 per week. Friends (more like acquaintances) had a family holiday home that they wanted to rent and we needed somewhere to stay.
We had friends who had friends that owned a beautiful lakefront house that could sleep a couple of families. Not sure the price, but he said it was really cheap.
Timeshare Weeks
From USD$80 per week. If you know someone who has a timeshare, you can get them to enter into a community that either swaps or lets you rent a timeshare.
Missions Organisations
Some missions organisations have holiday or retreat houses available to rent. We were able to rent a beachfront house. It wasn't in the middle of nowhere either. It was a world famous beach. It was around USD$30 per night.
Union Organisations
Some union organisations have accommodation that they rent out to their members and dependents.
Work Welfare Trusts
Sometimes organisations have or subscribe to trusts that have access to accommodation. When I worked for NZ Post a fellow employee told me about their accommodation scheme. My wife and I were able to honeymoon for a week in Christchurch and a week in Queenstown, NZ for USD$80 a week.