4 Questions Every New Vacation Home Investor Should Ask Themselves Prior to Purchasing A Property

3 min read
Trey Duling

Trey Duling is the President/CEO of OrlandoVacation.com, a large travel company specializing in Florida getaways. He has over 27 years of experience in the area, owning multiple companies that market to guests looking for an Orlando vacation. His main focus is marketing hotels and short-term vacation rentals near Disney World, with ample expertise as the largest authorized ticket seller for the large attractions in Orlando.

Raised by his father who previously owned multiple hotel properties, Trey gained a lot of knowledge growing up around the hospitality industry. He learned early on what general managers for hotels were looking for in a marketing company to help them sell more rooms per night and has been actively growing his hotel portfolio since 1993.

In 2006, Trey expanded into the vacation rental home market by offering his guests condos and townhomes to rent within a 15-minute drive to Disney World. With the increasing demand of this type of accommodations, he now markets over 380 condos, townhomes, and vacation homes in the area.

Packages are the most popular among guests, as they offer more savings when bundled with lodging, and OrlandoVacation.com is the largest ticket seller for the area’s attractions today.

Trey graduated with a bachelor’s degree from the University of Mississippi and then received his master’s degree in Entrepreneurialism from Belmont University in Nashville, Tennessee.


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Often times I have vacation home owners come into my office, and explain to me that their vacation home is causing their family to have financial hardship.

Often times these investors were sold a bill of goods at a trade show or by a realtor looking to make a quick commission check. Sometimes these realtors go through the numbers and show the investor how they are going to make money every month, and this is a very safe investment.

While I do agree, that buying a home in a popular vacation community is a safe investment it is far from being risk free. We only have to look back about 7 years to find proof why many vacation home investors should be weary. Here in Orlando, there are many vacation homes, town homes, and condos that were purchased 7 or 8 years ago for more money than they could be sold for today. Ouch, seven years of no appreciation.

4 Questions Every New Vacation Home Investor Should Ask Themselves:

Here are a few questions every new vacation home investor should ask themselves before purchasing a property:

1. Are You Able to Put Down a Large Deposit?

If you are not able to put down a large deposit or pay for the property with cash, then you need to be cautious. Most lenders are really making it difficult on investors to buy a vacation home without having at least 30% or more down. If you elect to pay a higher interest rate, be very careful as this is how many vacation home owners get themselves into trouble.

Related: 5 Ways To Get Down Payment Money To Purchase Investment Properties

2. Are You Financially Stable? Are You Able to Feed the Vacation Home Every Month?

A good property manager should be able to break you even on your monthly bills, your HOA payments, your property taxes, your insurance premiums, repairs and chip in every so often on the mortgage payments. However since every market has high and low booking months, I like to caution investors to look at their mortgage payment and feel comfortable that they could pay that amount every month without much hardship on their family finances. If you cannot do this then I would suggest looking for a less expensive investment or wait until you can put more money down.

3. Do You Have Extra Time Which You Could Devote To Your Vacation Home?

A lot of investors I know come down to their house every year and do a lot of preventative maintenance and upgrades themselves. This saves them a lot of money. Another way investors can make their vacation homes more profitable is if they do majority of their own bookings. Marketing a vacation home is expensive, and this cost property management companies money so they pa y the owner 65% to 75% of what the customer pays them. If an investor can book his own vacation home, then he can make this extra money on each and every booking going into his house.

Related: 23 Totally Awesome Life Hacks for Landlords (To Save You Time, Stress, and Money!)

4. Do You Like the Area Where You are Buying a Vacation Home?

You need to be present and active when you own a vacation home and you need to come by and check on it at least 2 or 3 times a year. This way you can make sure the property is being kept up to your standards. It sure makes these visits more enjoyable if you feel like you are going on vacation rather than look at it as a job.

The best advice I can give any new vacation home investor is to take your time and do your research. If someone tells you that you have to act now to get this great deal, slow down and do your due diligence. Not every vacation home makes money, if they did everyone would own one.

Be cautious when buying a vacation home, consider buying a condo or townhome first to see how you like owning such an investment. If you like it, you could always sell this unit a buy a bigger vacation home in the future. Remember, there are always more demand for investments that are less expensive. So if you started off with a condo and you did not like the return or the demand on your time that this investment is requiring from you, it is easier to sell a $100,000 condo than it is a $450,000 vacation home.

How do you feel about starting small like in a condo?

Be sure to leave your comments below!