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How to Build Your Own Vacation Package Deal

Are you looking for vacation package deals on Maui? It might be worth the time it takes to put together your own vacation package. Booking directly from owner saves you money, requires little time and can bring you more satisfaction. There is all the necessary information out there on the Internet, even more than you need, but the search does not have to be intimidating. I do all the bookings for my own trips, and I am going to explain this process here in easy-to-follow steps.

1. Conceive. Decide on approximate dates for your dream vacation
2. Search. Do a couple of preliminary searches for accommodations and flights
3. Refine. Narrow down your dates based on availability and rates
4. Confirm property. Put on hold at least two properties until you buy your flights
5. Buy flight. Buy your flight tickets
6. Book property. Book you accommodation with owner
7. Rent a car. Select and book your transportation
8. Insure. Buy protection for your trip

1. Conceive

You are ready to go on vacation. What is your dream destination? Even though this site is all about Maui – the best vacation island in the world, according to many reliable travel polls – the process I describe here fully applies to any vacation spot you choose.

Think about what dates work best for you and how long you would like to be on vacation. Decide if you dates are firm, or you can allow some leeway. If you are really flexible, prepare a list of possible time frames.

You might want to do some reading about the island to help you decide where you would like to stay in Maui, especially if this is your first trip to the island.

2. Search

After you have decided on tentative dates and the area you would like to stay, you are ready to search for accommodations and plane tickets (we are talking about Maui here).

Accommodations. There are many web sites where owners list their vacation rentals. One of the largest and most popular is We invite you to browse our collection of Maui rentals as well at Look what accommodations are available and at what price. To save my time I look only at properties that have online availability calendars. If owners publish their phone number, I call them. It’s a great way to get information and feel of the property. Make sure you write down as many available and appealing properties as you can find, noting exact dates of availability, rates and fees.

Flights. At the same time check availability and pricing of the flights. I like to do my preliminary searches on Travelocity. They have a good interface, response time and presentation of results. Other great resources are and Write down all options that are acceptable to you. At the end of this step you should have a list of available flights with noted dates and times, airlines, number of stops and prices.

First time, spend no more that 20 minutes on both accommodations and flights. You might find out that there is limited availability or the pricing is over you budget. If this is the case, make adjustments (dates, budget, number of people, etc.) and go through the search again. I usually make it 2-3 times through before I find suitable availabilities and get comfortable with pricing and dates.

3. Refine

By now you should have a list of properties and another list of flights. Compare the two lists, refine your dates and decide on 4-6 quality accommodations to request.

4. Confirm property

Go through the list of properties you refined in step 3, email or call every owner to request availability and detailed quote (rate + fees + tax) for every property. Tell the owner that you are very interested and ready to book to distinguish yourself as a serious potential renter. Ask additional questions you might have about the property. You might have to wait to get all responses. I usually don’t wait more that 24 hours. If the wait is acceptable, you might repeat some requests in 24 hours.

As you get responses, put the most appealing property on hold for 24 hours to buy your tickets and keep 1-2 other properties in reserve. I always honestly tell the owner that I consider 1-2 other properties, that I am ready to buy the flights and that I am asking to hold the property for me for 24 hours. Most owners will do that for you. Ask the owner to email you a contract or a rental agreement.

5. Buy flight

Knowing the dates, and having a list of flights from your search in step 2, this is very straightforward.

6. Book property

In step 4, you asked an owner to email you a contract or a rental agreement, and you probably have received it by now. It is time to confirm with the owner, and send the deposit and the contract/agreement. It is nice to write back to other owners whose properties you considered, thank them and explain that you made your selection.

7. Rent a car

Most people like to rent a car to explore Maui. First, I check on car rates on Travelocity. I decide what size I need and write down the best rate. Then I go to Priceline, and bid 30% less. Usually I get what I want from the first attempt. If not, I have to change the dates or the type of car, or just wait a couple of days to submit a new request. I have always been able to save on cars with Priceline, but be aware that with them you have to pay right away and the purchase is not refundable. When you rent directly from rent-a-car companies, you don’t have to pay until you pick up the car, and you can cancel at any time with at least a 24-hour notice.

If you don’t need a car while on Maui, but need a transportation from and to the airport, I can recommend
SpeediShuttle. They offer door-to-door service and you can get a fare quote on their web site.

8. Insure

By now you have booked your accommodations, flight and car, and spent a lot of you hard-earned money. Yet your plans can be so quickly ruined by an unexpected emergency in your family, lost baggage,
airport closure due to a storm or any other unforeseen event, that it is definitely worth to protect yourself with a travel insurance policy. I use Travel Guard for my own travel protection.

As one of the leading travel insurance providers, Travel Guard covers more than 6 million travelers worldwide
each year. Their travel insurance plans offer coverage for trip cancellation, travel interruptions and delays,
emergency medical and health expenses, lost baggage and more.

Lost luggage, trip cancellation, medical emergency


* While I used the web sites and services described in this article and can recommend them to you, I can not guarantee every experience to be problem free. Neither I nor will be liable for any loss or damage or simply less than positive experience arising from following the advice in this article.

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