Anyone STR investing in Kissimmee Florida? If so, how is it for you?

Question

Hello!I am located in Orlando, FL and am brand new to the real estate investment world. Over the past few months have read books by Brandon Turner, Robert Kyosaki and Tom Wheelwright and am ready to scale in with my first property and begin the REAL learning process :) I'm planning on focusing on STR due to my location and distance to the Disney parks. I would also like my first property to be close to home so I can manage it myself (in order to learn how to manage a management company).I've been reading a lot of the new posts on here, which has been EXTREMELY HELPFUL, but I figured I would ask my own questions due to this being market-specific.1. For those who are investing in Kissimmee, how is the market today? I know it is highly saturated. How difficult is it to find a STR opportunity that cash flows? Is 10-15% COC possible right now with STR in Kissimmee? Also, what specific areas in Kissimmee are better than others?2. I figured the easiest way to find opportunities quickly is through an investment realtor. From what I hear, you have to jump on opportunities quickly and having someone who knows how to help us quickly find and properly analyze a property would be key for us. I do also see convo surrounding sites like airdna.co for property finding. For someone who is just starting out and doesn't have an eye yet on what to look for, would you recommend just working through a realtor?Thank you in advance!Josiah

Josiah Earl · Answer

Thanks for sharing, @Kyle Mccaw! I’m looking into resort communities now and hearing your experience with your community is helpful.

Shawn McCormick · Answer

@Josiah EarlI'm right here in Orlando too, happy to meet up or have a call to discuss. I add my two cents in many of the posts regarding STR if you want to dig thru some of my answers. There are a lot of nuances that you will want to be aware of and questions from you that I would want to make sure you understand well enough before advising you on where to invest specifically. I have a map of my top recommendations for communities to start with, but depending on your budget, we could look elsewhere.One thing I might suggest is to consider speaking directly with a local PM that has real data from actual homes being rented rather than relying just on an algorithm site. Happy to have a call or zoom if you like, best of luck!

Shawn McCormick · Answer

@Eric DePoto I'll send you a PM.

Eric DePoto · Answer

@Kyle Mccaw, @Shawn McCormick, The gentlemen here are all great with being so outpouring with the info. Question, what additional fees are usually associated with this? I too am looking into this and I am seeking some information/direction. I would like to get into a similar style of resort like WH but may look at others. @Josiah Earl what other resorts are you looking at?

Kyle Mccaw · Answer

@Josiah Earl I purchased a 5 bed / 5 bath STR in Windsor Hills Dec 2021. My logic was I wanted something for 2-3 families to share and be super close to everything. I spent $$ updating it, creating a gameroom and theming the kids rooms. In my opinion that is required to compete with the other properties. I chose W.H. because it is crazy close to the parks and everything along 192. The homeowners in W.H. are very active in promoting their resort and helping everyone be successful. Search them out on FakeBook. I haven't seen that level of involvement at the other resorts. If I purchase in another resort I would give some thought to Storey Lake with Universal Studios EPIC park opening nearby. You can see mine at: www.OurDisneyHome.com

Samuel Leatherwood · Answer

You are taking all the right first steps, Josiah. Keep it up!

Josiah Earl · Answer

Hello @Shawn McCormick, thank you for the info! I would love to connect. I will send you a message :)

Josiah Earl · Answer

Thank you @Mark Munson! Very helpful info! That’s good to know about higher priced locations. Are there some areas of the city that are favored above others that stand out to you?

Mark Munson · Answer

Hi @Josiah Earl I'm in Orlando as well, we operate a mortgage brokerage that secures financing for investors, so I know the market well. Firstly, I would start attending either of the two Real Estate Investors Associations here. You will meet like-minded people and other local STR investors, as well as many other resources. Secondly, I would try and find a good realtor like you mentioned, but one that is specifically an investor too. Thirdly, you need to connect with local wholesalers, as they are another source of off-market deals. Lastly, to seperate yourself from a saturated market, it is generally best (if possible and financially feasible) to operate in a higher price point for STRs in Kissimmee, as they are less impacted by an over-saturated market. There is a lot more to unpack there, but figured I'd mention it. I have many clients that buy in the $500-$2M range, and they stay booked and profit well. If you ever need anything here, feel free to reach out to me. I'd be happy to discuss further if you need more help. Best of luck!