5 Steps of Short Term Vacation Rental Investing

vacation rentalYou’re about to discover a new twist, thanks to technology, on the age-old concept of short term vacation renting of a house or of a condo. Not just so that you can have a vacation home, like I described in a previous training, “How to Make Your Vacation Home Dreams a Reality”. Instead, in this training, I’m going to take this concept to a whole new level and focus on short term vacation rental from an investing standpoint.



Five Steps to Short-Term Vacation Rental Investing


Airbnb, VRBO, HomeAway, and now to a lesser extent, TripAdvisor, have opened up an amazing way to make more money with a rental. I have a video called, “Three Ways to Turn a House into a Cash Flowing Machine”, where I introduced the concept of producing more profits with a house by converting it into a short-term vacation rental.

In order for this concept to work, you don’t necessarily have to be in some far off Caribbean island or a ski resort. Short-term vacation rentals can be successful in many locations because they are competing against the local hotels and motels. More and more travelers are travelling as a family and want more space when on vacation. Now, thanks to technology, we can put this altogether and put it directly into your hands instead of using a local property manager.


1. Do Your Research


  • Legality: 


The idea that someone can put their house up as a short-term vacation rental is a relatively new concept in legal terms. This means that a lot of these houses are in residential neighborhoods and are zoned as a single family home. Not all communities will have laws for short-term rentals but some will put a law in place that says you cannot rent for less than 30 days.

Make sure you research the legality before converting a home into a short-term rental. You do not want to go ahead and turn your home into a short-term rental and secure bookings as far as a year in advance, only to be shut down by the government.


  • Market Research


To ensure your vacation rental will be profitable, you need to look into other vacation rentals in the area. Check out your competitors on HomeAway.com and AirBnb to see what their nightly rates are and then look at their calendar to see how booked up they are. You might even consider calling a local property manager for more information.


  • Profit VS Cost Research


You can use a booking agent to research some of your competitions profit statistics. Look at what they’re bringing in, and most importantly their gross revenue. Gross Revenue is the actual rental money that could go to you as the owner.


Deduct Your Bills


If the gross amount is $45,000, then next  you need to subtract any extra costs. With a short-term vacation rental you will be paying all utilities, cable and internet. Don’t try to cut corners on the cable and internet because most travelers will want to have them available during their stay.

Other expenses include things like lawn care or possibly pool care. You’re going to need to look at what revenue the vacation home will generate.  Is it significantly more than it would make as a normal rental?


2. Sweet Spot Property


What type of property is going to give you the most beds, at the least amount of cost, but also has amenities? If you’re in the Smokey Mountains it’s going to need a view, be easily accessible by car,  and preferably be  a log cabin.  If you’re near the water you will want to be close to the beach, but you don’t necessarily have to be waterfront. Waterfront properties typically cost more but they don’t generate nearly enough revenue to compensate for the cost of purchase. It is best to be close enough to where it’s not a long bike ride or a really long car ride to the ocean.

The best way to figure out what amenities your property needs is by  studying what your competition is and what they are putting in their ads. Really research what they’re offering to pick up on ideas on what amenities you should provide.

Another important factor is a house’s Sleep Number. The number of people that a rental sleeps is a huge determining factor on how much

money you can make. If a property has limited rooms, you can improvise by adding a pull-out couch or even bunk beds to a bonus room. The sweet spot property has the amenities, the beds, and then it has to  have a ” Wow Factor”.


Wow Factor


The “Wow Factor” is the reason why people love your property and want to take a vacation there. For instance, the Smokey Mountains has a great view or if you’re just in a major city,  it may be accessible to the subway, or have something  there that people are really, really going to like.


3. Renovate and Furnish


Typically there are certain things that you need to accomplish in order to make a vacation rental more traveler friendly. You can win big by how you renovate and furnish your vacation home, so be sure to make it very homey and comfortable. Nice furniture, wall decor, and basic essentials a traveler would need like pots and pans, towels, and all of the little things, will help your guest feel right at home.

This is by far the biggest difference between a normal, traditional investing arrangement versus a  short-term rental.  You’re going to have to pay to get it furnished, and this can be $10,000, $15,000, or even $20,000. This will be more difficult for those that are cash challenged because you can’t typically borrow money on furnishing unless you get a credit card with high interest rates.

If you look at the math and the property is going to be very profitable then the furnishings are negligible. I typically pay off the furnishings for my properties in half a year.

Make your vacation rental wonderful; make it a home and it will have a huge impact on your star ratings which makes a big deal over time.  This will also have a huge impact on the ability to get the vacationers  to come back. Ideally, you will start building a brand where people want to stay in your properties because they’re amazing and have all of the little things that most competitors don’t.


4. Booking Agents


Short-term rental platforms like HomeAway, Airbnb, VRBO, and TripAdvisor, require you to respond in 24 hours or less. That’s not freedom. With a traditional rental you just have to pick up your rent each month, maybe pick up a phone call or two, or you can hire a property manager to do it for you. A booking agent is kind of like a property manager only they’re more suited for this particular industry. They’re the ones that are handling the property inquiries that are coming in on a daily basis.


Evolve Vacation Rental


One of the biggest booking agent companies out there is Evolve Vacation Rental Network. This group is  wonderful because they don’t just pick up the phones, they  also manage your listings. If you don’t know how to set up an Airbnb, VRBO, or HomeAway listing account very well then you’re going to be in trouble because that’s where all the bookings come from. These people have already figured them all out and they’ll manage it for you.


Dynamic Pricing


Another big thing a booking agent company will do is dynamic pricing. There are tools available that the hotel industry has been using for ages where they dynamically price the unit based on the time of year, whether it’s peak week or not because there’s an event coming to town, and based on what the competitors and hotels are charging. It’s amazing.

If you want to build your own vacation rental listing accounts then I would suggest using Wheelhouse. Pricing is going to make or break you in this game. If you price too low and someone books that slot of time, you won’t get that money back.  If you have short changed yourself, you’re going to lose money.  Wheelhouse has been a game-changer for me because it dynamically prices. I was blown away by their algorithms because they were pricing some of the peak weeks a lot higher than I was. So I made the adjustments and still got the bookings, just more money. A booking agent like Evolve Vacation Rental will also dynamic price for you.


5. Bookkeeping


This is above and beyond the normal bookkeeping of a property management system. You now have to deal with what’s called “occupancy taxes”. This is what hotels and motels have been dealing with as long as it’s been in place. 12.5% to 13% is normal. This gets paid above and beyond what you get paid. You can charge this to the guest so it’s not going to be an expense to you, but you do have to pay the government what you collect.

There’s a service called My Lodge Tax  that will do your bookkeeping for you.  One of the most frustrating things about setting up occupancy tax is the amount of time it takes to set up the licenses and get everything in place. One of my properties took over 10 hours to get set up just so I could pay the government. Mylodgetax.com supposedly will do this for you. I haven’t used them but they’re recommended by HomeAway so they might be pretty good.


Other Benefits of a Vacation Rental


A Vacation rental is obviously more complicated than the normal, traditional rental, but it can make more money. Another benefit is that you don’t have to evict anyone because they are travelers, they’re coming in, and they’re coming out. Evictions are non-existent. In the world of normal, traditional rentals, evictions are very common and it’s frustrating because the laws are setup mostly to protect tenants, so landlords typically get screwed.

The next thing is you get your money upfront, so you’re not chasing tenants for rent. They’re paying you up to a year in advance, so you always get your rental money.




Research: Make sure you’re picking up properties that are profitable, as well as legal.

Sweet Spot Property: Have a good sleep number and the amenities that travelers are looking for.

Renovate and Furnish.: The better you furnish the better off you’re going to be

Hire a Booking Agent: Not only do they help with the listings and dynamic pricing, but they also can help coordinate with the cleaning and the maintenance.

Bookkeeping. It’s important to pay your taxes as well.


All these things have to be in place. When you do that, this can be a magical formula. You can make a lot more money for the same property you currently have that you might be doing a traditional rental on.



  1. Thanks for all your informative and amazing Videos.

  2. Good stuffs, thanks for the eye opening video as always.

  3. Great video very good information

  4. Sonia Santos says:

    Thanks for sharing this wonderful idea of real estate investing. I learned a lot.

  5. Thank you happy Thanksgiving

  6. Christopher Berggren says:

    Thanks, Phil, for this particular video and all the others. This one in my email this morning is well-timed, as I’m moving to Florida West Coast for the winter. No more winters for this Cali turned NYer guy!! Tampa is one of the country’s highest foreclosure cities, so I am looking at nearby St. Pete, still large # of foreclosures but next to the beach. With no job, nor cash, and only fair credit, how can I get into a SFR or Multi-unit fairly quickly?

  7. Cliff Fung says:

    Thanks Phil for sharing the best vacation rental investing idea.

  8. Virgil Watson says:

    Thanks Phil for that information the best vacation renal investing idea.

  9. Good summary, and great that it comes with service links! Missing the turnaround services, though – i.e. locking-unlocking, cleaning, repairs. This can also break the business, as it can easily go bad. Unreliable cleaning person – and voila, bad reviews. Also, if there’s a problem with utilities, it must be fixed the same day, which is tougher.

  10. Cody Dayley says:

    Good stuff thanks for the info……Happy holiday’s to you and your family and your team.

  11. Barbara Pollard says:

    We are doing this same thing with our house using Airbnb & VRBO. We are lucky that our house is located in Willow Glen area of San Jose, CA. Not only is WG a desirable location, but can take advantage of Corporate Housing and Trade Shows in Downtown. It’s important to also research the local hotel room rates and parking fees. That helps to determine what to charge plus a great perk to provide free parking.

    Another tip is to partner up with another person doing the same thing with their property in the general area. You can be ‘sister’ properties; if John’s property is booked, he can direct a guest to your property on his page, and vis-versa. Great marketing tool.

    Also, there are reviews offered by other owners who rented their house to guests–who are good, who are bad. A good protection against damages or misuse of your property. Find a reliable Handyman, house cleaners (we hire people who are already working for local hotels and know how to clean/prepare are premise quickly and professionally), and gardeners. Once you have a good crew, pay them a little extra because they will increase your profits due to their reliability and doing the job right the first time.

    Most importantly, look at the profits from a year-to-year viewpoint, not month-to-month. There are periods during the year that bookings are slow. Then there are periods where bookings are crazy-busy–sometimes making $10,000/month. Don’t become too discouraged during the slow periods. It’s a flexible investment opportunity.

  12. John Mahoney says:

    I agree that doing your research on renting vacation homes can help you find the best.

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