Michael Chen PA, Realtor at La Rosa Realty Celebration
Published on July 31, 2022



Our First Family Trip to Disney in 2017

Once upon a time, in a faraway land, a young prince lived in a shining castle….oops wait a minute, different story…

Let’s try this again…

Our Disney journey dates back to the spring of 2017 when my family and I visited Disney World, Florida for the first time. Let’s just say, I won father of the year in 2017. It all started when my kids told me when they visited Magic Kingdom, “Daddy, this is the best place ever”.  It then dawned on me that I can have an amazing time with my family here year after year and create memories to last a lifetime. We had been looking at short-term rental opportunities all over the country but couldn’t really find a place that we could rent year round and a place we feel excited about coming over year after year.

Disney is the land of magic, a place where children’s dreams get fulfilled. If you think I’m joking, ask a random kid where they would like to vacation, and the answer will always be ‘Disney World’. It’s every parent’s dream to take their children to the most magical place on earth – Disney World. Such memories are the main reason why this place exists. Watching our young ones beam with excitement and joy melts our hearts like nothing else. The cherry on the icing is that we end up being the heroes for taking our children to Disney. This trip is worth everything and much more. After a visit to this magical place, many people dream of having a home nearby, a home away from home. This is what triggered my thirst to own a vacation home near Disney. The decision to invest in a vacation home by Disney was the perfect choice for us because it checked off all of our boxes;

  • Millions of visitors all year round
  • Disney is an international destination.
  • My family loves Disney, especially my 2 little ones.
  • Affordable homes compared to the national average
  • Opportunity to make money

After settling on buying a vacation home, the search started and we successfully purchased our first short-term rental property in Regal Palms Resort. This was just two months after our initial visit to Disney World. It’s been amazing how after this initial purchase, we have successfully purchased ten more vacation homes in various popular resorts in Windsor Hills, Windsor Palms, & Emerald Island. We are also now managing homes in other wonderful resorts such as Solara, Storey Lake, and Windsor Island.

Let me help you accomplish your dream of having a vacation home in Orlando by sharing a few successful tips.


Start thinking like a business person. Ask yourself some critical questions such as;

  • How much money can I make on this property by studying comparable homes on booking sites such as Airbnb/VRBO?
  • Who are my competitors?
  • What do I have that my competitors don’t have? (What’s your niche?)
  • What kind of home should I buy? (Condo vs. Townhouse vs. Single family home).

This is how I started before I purchased my first rental property.  I studied several similar homes before purchasing one.  I always study the most successful ones because this is how you can learn to make your property better.  Always study the homes that are successful and learn from the top hosts.


The location aspect is very important for a start. Disney World is big and so is Orlando. Knowledge is key! Gain as much insight as you can in regards to the perfect location for your investment. This will involve interviewing several real estate experts and agents in the area before settling with the best. An ideal agent, in this case, is one who has also invested in short-term rentals; as such, they can guide you through not just the purchasing process but also all the key components that will make your home successful in the long term. You need to ask yourself a few questions first by putting yourself as a guest taking your kids to Disney for a week;

  • Are the probable guests looking for a home that is close to Disney?
  • What amenities attract and are important to guests on vacation?
  • Would guests prefer a home with a pool or a home in a resort setting with pool, lazy river etc?
  • What kind of property would you book for near Disney World?
  • What’s your budget for a week’s stay?


Budget is the aspect that will distinguish you from other forms of property or vacation homes near Disney World. You need to establish a niche in the industry that will give you a competitive advantage and make guests comfortable with your pricing. The most important question when making a budget is; how much are you able or willing to invest in the kind of property you want?

Before settling on a certain budget, consider the following factors;

  • Utilities
  • HOA fees
  • Property taxes and insurance
  • Property Management Fee – Typically about $150/m
  • Booking fees – Typically 15%-20% of gross
  • If you are purchasing the property unfurnished, then you need to budget the cost of furnishing the home.
  • If you are purchasing an older home with few updates, you need to budget replacement costs such as AC, pool heat, furniture replacement, theming, etc

My best recommendation is to start with the budget that you feel comfortable with because I like all the homes I own and each of them has achieved the financial goals I have set for them.


  • Do you plan to be actively involved as a host or hand this property to a property management company after purchasing?
  • Do you have the time to manage guest inquiries and receive calls from guests 24/7?

If you enjoy guest service and have the time to invest in this business, you should host your guests (Do the bookings yourself) because this will be a great way to learn about the industry, save money, and add value to your business.

Hope you enjoy reading my blog post. My name is Mike Chen and I’m a real estate agent in the Orlando, FL area specializing in vacation, investment, and residential homes. I’m a huge Disney fan and I absolutely love this area. I would love to talk to you about what it would take to get you into a new home in this area. I look forward to speaking with you!

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