Advise on Purchasing my first STR in Kissimmee Florida

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Advise on Purchasing my first STR in Kissimmee Florida

Trevor McCormick
Investor · Sarnia, ON Canada · Member since 2025 · 6 posts · 1 vote

Hi All, looking for some advise or mentoring on purchasing a short term rental property in Kissimmee Florida.

1)Is it still a good investment with the current prices?

2) how to get started and what property management company to choose?

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Josh GreenBusiness Member
Realtor · Tampa/St Pete/Clearwater/Bradenton · Member since 2020 · 396 posts · 353 votes
1y
Quote from @Trevor McCormick:

Hi All, looking for some advise or mentoring on purchasing a short term rental property in Kissimmee Florida.

1)Is it still a good investment with the current prices?

2) how to get started and what property management company to choose?


The price you pay for being part of the Disney World spoon-feed of guests is that the barrier to entry for profitable STRs (ones that leverage close to or max LTV) is very, very high.

The benefits of Kissimmee for a newbie is analyzing property potential is very easy - you will have a ton of carbon-copy comps to look at and the online estimators like Airdna can actually be pretty accurate.  The con?  The majority of investments is a game of "race to the bottom" and "who holds the cheaper debt" card. 

To have a successful STR I HIGHLY recommend listening to this episode of a podcast: https://podcasts.apple.com/us/podcast/on-the-market/id161508...

Once you listen to this, and any highly involved STR operator will agree, you will find a lot of the fundamentals are lacking in Kissimmee or you have to have deep pockets to hit those.

I won't spoil the episode, but if you listen to it (and anyone out there that does) feel free to DM me afterward and I'd be happy to talk details tailored to your situation on if you're on the right path or maybe I can help.

[email protected]801-441-8891
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  • Raymond J. RodriguesBusiness Member
    Lender · Miami, FL · Member since 2017 · 1k+ posts · 797 votes
    1y

    @Trevor McCormick I would say that it is an okay market but is very saturated and alot of investors are having a tough time right now. Especially if you are hiring property management. Not to say you cannot do well, but it’ll take some extra TLC. @Shawn McCormick is local to the area and can share some of his experiences. 

    A little bit off to the west is also a solid market where you can find some success in the Tampa Bay Area. @Josh Green is the local expert there. 

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  • Shawn McCormickPro Member
    Realtor · Central Florida-Orlando · Member since 2014 · 1k+ posts · 892 votes
    1y

    Thanks @Raymond J. Rodrigues Hi @Trevor McCormick, looks like we were meant to work together ;). #McCormick

    I have some Youtube videos (link in my profile) that will help with some of your questions and I'd be happy to have a call to help walk you through the market and what you should consider when looking here. It is a very competitive market and units in the tens of thousands. If you do it right, you can be very successful. 

    Feel free to reach out and we can schedule a call. Best of luck!

    0Reply
  • Andrew SteffensBusiness Member
    Tampa, FL · Member since 2022 · 3k+ posts · 3k+ votes
    1y

    IMHO there are stronger, less saturated markets in FL.  Look West, and South East!

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  • Trevor McCormick
    OP
    Investor · Sarnia, ON Canada · Member since 2025 · 6 posts · 1 vote
    1y

    Thanks @Raymond J. Rodrigues for your feedback and recommendations. I am just in the starting phases of potentially purchasing in Florida so I appreciate any comments to help me along the way.

    0Reply
  • Trevor McCormick
    OP
    Investor · Sarnia, ON Canada · Member since 2025 · 6 posts · 1 vote
    1y
    Quote from @Shawn McCormick:

    Thanks @Raymond J. Rodrigues Hi @Trevor McCormick, looks like we were meant to work together ;). #McCormick

    I have some Youtube videos (link in my profile) that will help with some of your questions and I'd be happy to have a call to help walk you through the market and what you should consider when looking here. It is a very competitive market and units in the tens of thousands. If you do it right, you can be very successful. 

    Feel free to reach out and we can schedule a call. Best of luck!

     @Shawn McCormick definitely meant to be!! I have seen a few of your videos, they give some great insight of the market. I will keep you posted if I pursue investments in Kissimmee, I appreciate the feedback!

    1Reply
  • Ryan MoyerBusiness Member
    Property Manager · Orlando Kissimmee Davenport Salt Lake City, Park City · Member since 2019 · 993 posts · 1k+ votes
    1y

    @Trevor McCormick I have a lot of properties in that area.  If you want some revenue numbers for similar properties to the ones you're looking at or anything to use in underwriting feel free to reach out.  Just make sure you're actually putting pen to paper and doing your due diligence on underwriting.  It's a competitive market and most of the people that get in trouble here are ones that buy blindly without actually figuring out the numbers, etc.

    You'd be surprised the number of times I get asked after month one if their electric bill of $xxx or whatever is normal, and the thought running through my head is "how did you not  check things like that before you committed half a million dollars to something?"

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  • Jeremy Jareckyj
    Real Estate Agent · Salt Lake City, UT · Member since 2020 · 490 posts · 205 votes
    1y
    Quote from @Trevor McCormick:

    Hi All, looking for some advise or mentoring on purchasing a short term rental property in Kissimmee Florida.

    1)Is it still a good investment with the current prices?

    2) how to get started and what property management company to choose?


     I have heard from a few operators there that is super competitive. My suggestion would be to get an investor friendly agent who knows a few local markets and have them guide you in the right direction.

    0Reply
  • Jordan Lulich
    Attorney · Vero Beach, FL · Member since 2017 · 15 posts · 6 votes
    1y

    @Frank Mongiello is a great resource for a real estate agent in Central Florida and South Florida. He has helped many real estate investors and really understands the niches in these areas for real estate investments. I would reach out to him if you are a real estate investor who is looking to build your portfolio in Florida. 

    0Reply
  • Trevor McCormick
    OP
    Investor · Sarnia, ON Canada · Member since 2025 · 6 posts · 1 vote
    1y
    Quote from @Jordan Lulich:

    @Frank Mongiello is a great resource for a real estate agent in Central Florida and South Florida. He has helped many real estate investors and really understands the niches in these areas for real estate investments. I would reach out to him if you are a real estate investor who is looking to build your portfolio in Florida. 


     Thanks for the recommendation!

    0Reply
  • Todd AndersonPro Member
    Real Estate Agent · Cape Coral, FL · Member since 2023 · 392 posts · 175 votes
    1y

    @Trevor McCormick,

    Is there a specific reason to only look at a single market.  Florida has a number of great markets that work well for investment properties, and a  number that no longer work.

    There are a few Florida markets that are still in the top growing markets in the country.  The investors that i work with look to theses growing markets of population and jobs to make an investment that both cash flows and will find appreciation.  

    One market, near where you are looking, that is still in this phase is the Ocala market. There they are seeing both a great job market, a number of large employers moving in, and are still in the top ten of population growth nationwide. I have worked with a number of investors who have found this to be a good market for REI

    Connect if i can help more. Best of luck.

    [email protected]651-492-5652
    0Reply
  • Trevor McCormick
    OP
    Investor · Sarnia, ON Canada · Member since 2025 · 6 posts · 1 vote
    1y

    Primarily for personal use for the family as well as an investment (but the numbers need to work), I am just starting out searching for a property so I am open to all suggestions and comments. Thanks Todd!

    0Reply
  • Josh GreenBusiness Member
    Realtor · Tampa/St Pete/Clearwater/Bradenton · Member since 2020 · 396 posts · 353 votes
    1y
    Quote from @Trevor McCormick:

    Hi All, looking for some advise or mentoring on purchasing a short term rental property in Kissimmee Florida.

    1)Is it still a good investment with the current prices?

    2) how to get started and what property management company to choose?


    The price you pay for being part of the Disney World spoon-feed of guests is that the barrier to entry for profitable STRs (ones that leverage close to or max LTV) is very, very high.

    The benefits of Kissimmee for a newbie is analyzing property potential is very easy - you will have a ton of carbon-copy comps to look at and the online estimators like Airdna can actually be pretty accurate.  The con?  The majority of investments is a game of "race to the bottom" and "who holds the cheaper debt" card. 

    To have a successful STR I HIGHLY recommend listening to this episode of a podcast: https://podcasts.apple.com/us/podcast/on-the-market/id161508...

    Once you listen to this, and any highly involved STR operator will agree, you will find a lot of the fundamentals are lacking in Kissimmee or you have to have deep pockets to hit those.

    I won't spoil the episode, but if you listen to it (and anyone out there that does) feel free to DM me afterward and I'd be happy to talk details tailored to your situation on if you're on the right path or maybe I can help.

    [email protected]801-441-8891
    Impact Realty Tampa Bay.4.962 Reviews
    WebsiteView Page
    Suncoast Vacation Homes4.959 Reviews
    View Page
    3Reply
  • Trevor McCormick
    OP
    Investor · Sarnia, ON Canada · Member since 2025 · 6 posts · 1 vote
    1y

    Thanks Josh, I will give the podcast a listen!!

    0Reply
  • Andrew Street
    Member since 2019 · 1k+ posts · 292 votes
    1y

    Hi Trevor! Kissimmee remains a strong market due to its proximity to Disney and other attractions. While prices have risen, there are still opportunities with the right approach. Start by researching local regulations and working with an agent experienced in vacation rentals. For property management, choose a company with a good track record in STRs and transparent fees.

    Happy to connect with anyone looking to share insights!

    0Reply
  • Fab Ragh
    Rental Property Investor · Bronx, NY · Member since 2019 · 46 posts · 6 votes
    1y

    Also looking to set STR around Disney.

    0Reply
  • Emily Valderrama
    Real Estate Agent · Member since 2024 · 2 posts · 1 vote
    1y

    Hi Trevor,

    I work at a local property management company based in Kissimmee and we are seeing quite a bit of STR convert to LTR because of the lack of reservations they had this past year. I'm happy to answer any questions you may have.

    1Reply
  • Alice Horn
    Property Manager · Kissimmee, FL · Member since 2019 · 446 posts · 266 votes
    1y

    Hey @Trevor McCormick (and @Fab Ragh) - as many have stated, Kissimmee and the Orlando market in general are extremely competitive. But people still flock to Disney, Universal is opening a new theme park in May and the area will always have new events and attractions to draw guests. 

    The key is identifying a home that is not cookie-cutter. Uniqueness is key. Start with great theming, keeping in mind the current trends taking place at the parks. A vibrant game room. Don’t forget the pool area- add pool games and perhaps a feature wall. On top of that, we have found that homes with a great view (forest or lake view), or proximity to the clubhouse tend to book better. 

    Sometimes you’ll find better deals with the older communities closer in to Disney. These homes may be dated, but they can be decorated to a high standard. Proximity to Disney is another competitive advantage.

    As property managers, we see what’s actually booking in all the resorts near Disney - the good, the bad and the ugly. Happy to chat and help you compare your options.

    1Reply
  • Chris Rich
    Property Manager · Orlando, FL · Member since 2023 · 107 posts · 64 votes
    1y
    Quote from @Ryan Moyer:

    @Trevor McCormick I have a lot of properties in that area.  If you want some revenue numbers for similar properties to the ones you're looking at or anything to use in underwriting feel free to reach out.  Just make sure you're actually putting pen to paper and doing your due diligence on underwriting.  It's a competitive market and most of the people that get in trouble here are ones that buy blindly without actually figuring out the numbers, etc.

    You'd be surprised the number of times I get asked after month one if their electric bill of $xxx or whatever is normal, and the thought running through my head is "how did you not  check things like that before you committed half a million dollars to something?"

    Seriously! I get blown away how many times this happens, especially with STRs in that area.  So many people bought with minimal or inaccurate information. And not knowing their numbers also makes it next to impossible to know if you have a bad PM that's eating into your cash flow as well (Like Vacasa charging $800-1000 a month for elecrtic on a 4/3, 2000sqft house with a pool). 

    @Trevor McCormick to piggyback off what others have said, determine if you are trying to maximize it as an investment or utilize it as a vacation home you will STR to help cover expenses, as this could dictate which type of property you are looking for. The good news about the saturation is a lot of investors bought in the height of covid, with abnormally high performance numbers. Many of them are now trying to sell, so there are deals to be had.

    0Reply
  • Sean Huynh
    Member since 2022 · 1 post · 1 vote
    1y

    Just sold my STR in Orlando at a pretty substantial loss. There are many reasons as a Canadian, that I would advise against investing in an Orlando STR right now based on my personal experience.

    1. Weak Canadian dollar
    2. Insurance crisis in FL
    3. FIRPTA withholding (Google it)
    4. Race to the bottom on rates
    5. Challenges renting to Canadians (friends/family), I had a few cancellations from Canadian travellers who were choosing to avoid travel to the US due to current political climate.

    Now, if you have deep pockets and can buy the property in cash, you can ignore everything above and go for it as you can probably cash flow without a mortgage. I had a 5 bedroom / 5.5 bath near Disney and rental revenue was $55-58K annually. 



    1Reply
  • Raymond J. RodriguesBusiness Member
    Lender · Miami, FL · Member since 2017 · 1k+ posts · 797 votes
    1y

    @Sean Huynh I'm sorry to hear about your experience. Perhaps you should look into Tampa Bay area. @Josh Green has a successful STR operation and is not as saturated as you had mentioned.

    [email protected]619-456-8311
    Helm Mortgage Corp.5127 Reviews
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    0Reply
  • Jacob Morgenstern
    Property Manager · USA · Member since 2018 · 87 posts · 50 votes
    1y

    Short Answer. Kissimmee/Davenport is an oversaturated market. If you have a Plan B to flip for a profit then go for it.

    1Reply
  • Patrick Arenson
    Member since 2024 · 8 posts · 3 votes
    1y

    Hi, We're an Orlando PM Company that specializes in long term, unfurnished rentals. I would not advise on STR in Kissimmee. Spring is usually high season and most of the owners we know are either trying to sell or switch to long term because they've been doing maybe 20-30% occupancy. It's also quite expensive to furnish and unfurnish. Happy to share more thoughts if you have any questions.

    0Reply
  • Ishwar Mahajan
    Member since 2023 · 3 posts · 0 votes
    7mo

    @Trevor McCormick What decision you finally made? I am exploring Kissimmee for STR and thought of checking with you on your experience if it worked for you?

    0Reply
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