Choosing Your Vacation Rental Manager in Central Florida

Finding the Best Property Manager

Hiring a Property Manager for Your Vacation Home

Whether you are an investor, or the owner of a vacation home that you purchased for family use. Renting it out is a big deal. Choosing the right person or company to manage it in your absence is a big deal.

There are a lot of moving parts in property management such as booking renters, caring for the property, and handling the licensing, taxes, and financials. It becomes even more complex in the short-term vacation rental industry. To protect your investment, you should hire a skilled vacation home management team with a solid track record in marketing, finance, guest experience, and property maintenance.

Your first impression is important. You want to look over all available information to help narrow your search. Most importantly do not stress out! There are a lot of choices out there when it comes to vacation rental management. We are here to help you find the right one.

Great vs. Mediocre Property Management Firms

Property management comes in all shapes and sizes. Just like banks, supermarkets, and car washes, some will meet your individual needs better than others. 

Size may matter. At the end of the day that is a subjective point of view. One that varies depending on who is looking. Some owners prefer smaller companies, because of the personalized service you receive. Others prefer larger management companies, because of the larger staff and possible resources. On the flip side, you can receive as poor of service and attention from any size management company. So, trust your gut and take the extra time to research what feels right for you and your property goals. It is all about how they treat their owners, guests, and employees. At the end of the day. There are great companies of all sizes and one can vary greatly from the next. There are many options when looking for property management companies. Especially the competitive vacation rental management industry. One management company does not fit all. So, make sure you have clear goals and expectations going forward. They will help find the right management company for you.

In other articles, we discuss the services you should expect from your property management company. The bottom line is that they should communicate clearly with you, follow ethical guidelines for handling finances, represent your best interests, and commit to moving heaven and earth to keep your vacation home occupied (and maintained). You need to make sure whoever you choose is constantly checking on your home and is easy to get in touch with. 

When you meet with a potential property manager, ask yourself this: If you were in the renter’s shoes, would you be happy to rent from this company? Is this the company we want our guests interacting with? If you get a bad vibe, trust your instincts, and keep looking. 

Begin Your Search

Figure out your goals and expectations early on. If you had a property management company before. What did you like about them? What did you dislike about them? What could be improved to provide you a better service and meet your goals. This will give you an advantage and a backstop to frequently refer to through the process. For example, is this only for investment? If so, then cash flow, occupancy rates, and of course, your return on investment will be important. Or, are looking to use the property part of the year? If so, you'll want to be sure renting the remaining weeks to cover expenses. Allowing you and your family to vacation for free. 

Word-of-mouth referral is always a great way to find the right property management company. Start with the realtor who helped you buy the vacation house, and then talk to neighbors or other owners of vacation properties in the area. Social media is big these days and there are many community groups that can help you narrow down your list. 

An exhaustive internet search is the most practical alternative. Start your search with the city or area where your property is located and add “vacation property management company”. You should also try different ways to word it, like “property manager for vacation homes” and “vacation property rental manager.”

For example, search for “best vacation property management companies in Kissimmee” or “Top vacation property management companies in Cocoa Beach.” You can also type in the community & resort you are looking to purchase in, followed by “management company.” 

Keep in mind that the organization that comes up at the top of the list of results may not be the best solution for you. They can be good at ranking highly on Google or have a much higher advertising budget due to their size. Often, they lack in other areas that count. Such as occupancy rates, and/or they have much higher fees to help cover company expenses. 

An easy way to keep track of your list of options is to create a spreadsheet in MS Excel or Google Sheets. Copy and paste the URL (web address) into the spreadsheet for each site that interests you. This gives you the link to easily open the website again, and lots of room to make notes.


Narrow Down the Options

Make a list of the services and features that are most important to you. In the end, you want to choose the vacation home management firm that is easy to contact, very responsive, pleasant to approach, and knowledgeable about the area surrounding your second home. You want to make sure that you can reach the person running the company with a phone call, text, or email. Sometimes communication chains can be clumsy, and owners have a hard time getting things pushed through to the top. You want to work with someone who views their job passionately and who puts their owners first. 

Finding a vacation rental company that is trustworthy, reputable, and honest is important. You want to build a relationship with your property management company. Look for a management company that builds their brand on core values you believe in. Look for a vacation rental company that values long standing relationships. You do not own real estate for the short term, so why choose a management company that will fizzle out? 


Analyze Each Website

For each company on your list, do a deep dive on their website. Is it easy to use? Do you like using it? Do you think renters will like using it?

Then get into their heads: What do they want you to know, and what do they hope you do not find out? Find someone who is honest and willing to give you the truth. Someone who will answer any and all questions you have for them. Likewise, if the company cannot provide you with actual revenue numbers from similar properties and past years. They may not be a good fit for you. 

If there is no mention of who you will be working with on the “about us” page, deduct some points. If they do not have an owner’s login portal to get statements and secure messages, deduct some more points. Do you like their story, how they got started? If not, you may want to deduct some points. Past history can be a good indicator of future results. 

You see where we are going with this, right? Now it is time to make a deeper cut. You should be able to have narrowed down your options to a handful of companies that you like. 


Interviewing Vacation Property Managers

Congratulations! You have made it this far and we could not be happier for you! Next up, the interviewing process, tips, and tricks! There are many items you should know and find out before you sign a contract with a property management company. Meet with them in person, if possible, and call them and discuss your goals and expectations. This is where you will be able to dig in and really find out if these companies will be a good fit for you. Once you have your goals and expectations in mind. You will find the search becomes less complicated. Below are some standard questions you may want to ask. Especially, if you are a first-time vacation rental owner. You will want to tailor this list to your individual needs, but it will get your started. 

The Interview Checklist

  • What is your first impression? Would you rent from this company, or person?
  • How big is the team and what kind of people have they hired? 
  • How did they get started? Why did they start their business?
  • How long have they been in the area - long enough to be quite knowledgeable? 
  • Side Note: Many vacation rental companies come and go. Make sure the one you choose will be there tomorrow. 
  • Are they available 24/7?
  • Are they there when you call? How fast do they respond to your questions, calls, texts during the interviewing process? 
  • Which services do they provide directly, and which are outsourced to a third party?
  • What are their core values - do they closely match yours?
  • Are there owner statements? How frequently are they sent?
  • Is there an online owner’s portal?
  • How frequently are owners paid out for rentals?
  • How do they pay you out? Direct deposit? Check? Wire Transfer?
  • Do they understand the complete vacation rental space? New trends, booking behavior, pricing strategies, etc.?
  • Do they change and adapt to the times? 
  • What is the seasonality of the market like?
  • How do they price your home? What data do they use? 

    Your management company should always be changing rates depending on market demand, outstanding supply, time of year, etc. If they are not then you can be sure they are not maximizing your revenue, or occupancy. Fancy algorithms sound great, but many times they fall short and represent poor attention to pricing and demand changes. 

  • How do they market and advertise your vacation rental? 
  • What are their occupancy rates like?
  • Do they know the “ins and outs” of those OTAs (online travel agents) like VRBO, Airbnb, TripAdvisor, etc.? 
  • Where are they running ads - websites, social media, blogs, Google?
  • Can they fill your unit during the slower months? 
  • What is the screening process for renters?
  • Is their contact easy to read and clear?
  • How long is their management contract and what are their terms?
  • When does the agreement expire, or renew?
  • How much do they charge owners & what are their fees to be in their rental and management program?
  • Are there fees for owners to use their property?
  • Do they charge you callout fees, trip charges, or miscellaneous fees each time they must go to your home?
  • Do they plus up service calls from handymen, HVAC technicians, plumbers, electricians, etc.? 
  • Do they plus up items they purchase for your unit? Such as light bulbs, AC filters, towels, sheets? 

You do not want to overpay for services provided by your management company. Find a reputable and transparent vacation rental company in the beginning- it will be worth it in the long-run. 

  • For major repairs and remodeling, do they hire licensed contractors, or do they try to do it themselves?
  • Do they have reputable vendors they work with for any necessary repairs?
  • How and when are repairs made when are you notified?
  • Is it made clear to the renters what they are responsible for?
  • Do they have a strict rental agreement for guests?
  • Do they have thorough check-out cleanings and inspections?
  • How are cleanings handled? What level of service and cleanliness do they provide guests?
  • What if something is damaged?
  • Are they providing guests with starter welcome packs? What do they supply? Is it at an additional cost to you as an owner? 
  • How much is the non-refundable deposit for late cancellations?
  • How are sales and use taxes paid out to the State and Tourist Development taxes to the County?



As you can see, there are many factors that come into play when choosing a vacation rental management company. No matter what your goal and expectations are. You want to make sure the company you choose has your best interests at heart. Be sure that you as an owner come first. Be sure the company does not nickel and dime you out of a cash flowing venture. If your goal is to vacation for free and let the property pay for itself. Make sure whoever you choose can provide services that help you achieve that goal. 

Do your research, interview the property managers on your shortlist, and spend a day or two reviewing their standards for owners and for renters. Choose carefully and deliberately and keep your second choice handy in case something goes wrong with your first choice.

 At, our business is our life. We love what we do, and we love being trusted by so many owners of vacation homes in the Orlando and Cocoa Beach areas. Read more about us.

If you are in search of a high-quality property management team, give us a call! We put our owners first and take less, so that you make more. 

Daniel Robinson


Vacation Central Florida

(407) 877-0777