STR (AirBnb/VRBO) Orlando—First Time Investor

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STR (AirBnb/VRBO) Orlando—First Time Investor

Katharine G.
New York, NY · Member since 2018 · 30 posts · 25 votes

Hi all!

NY based investor looking to get a vacation home in Florida (tale as old as time, right?) and seeking some wisdom for a rookie.

Interested specifically in Kissimmee/Orlando/Davenport as Disney market feels familiar to me and it’s generally a cheaper entry point than beach condos.

Looking at Regal Oaks (staying here now on vacation myself and enjoying it, though have read mixed things about occupancy), Windsor Hills, and Champions Gate.

Goal is to have a second home that I AirBnb out the majority of the year but also can escape to when NYC is ruthless (like now :) hoping to live in the 150-250K range, bonus if there’s a pool (regal oaks has community pool and individual hot tubs), and solid amenities.

Other than reading for my life, how can I number crunch and prepare for this? (Tricky to do now, especially) Anything you’ve done in this market that you wish you’d known about?

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Tyler GibsonBusiness Member
Real Estate Agent · Orlando, FL · Member since 2017 · 1k+ posts · 2k+ votes
5y

@Katharine G. I work with these types of assets and Partner With @Alice Horn of Villa Key management. They have the ability to create projections for any property you have an interest in. They build out the Pro-forma for you so you have an idea of what you are getting into. I would be happy to help in any way I can so feel free to reach out. 

[email protected]407-590-9858
GPG Team 596 Reviews
WebsiteView Page
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  • Claire Rosenberg
    Property Manager · New York City · Member since 2017 · 61 posts · 28 votes
    5y

    Hi @Katharine G.! Who doesn't love Flordia and second home loans rock with only having to put 10% down? I would recommend reaching out to hosts in the areas you are looking at and see how it has been for them. Also, I would check out Airdna to analyze the properties you are evaluating as a STR.

    1Reply
  • Amit Desai
    Member since 2020 · 56 posts · 22 votes
    5y

    Hi @Katharine G. we just bought one SFH in Windsor Hills. Please PM me for more information. I can definitely help you to understand and overview of market.

    Thanks

    2Reply
  • Amanda Ferguson
    Destin, FL · Member since 2019 · 55 posts · 50 votes
    5y

    @Katharine G. I would recommend connecting with @Piero Millares  He can help you out with an analysis on properties in the Orlando area.  

    2Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    5y

    Thanks, @Amanda Ferguson! Will do.

    0Reply
  • Tyler GibsonBusiness Member
    Real Estate Agent · Orlando, FL · Member since 2017 · 1k+ posts · 2k+ votes
    5y

    @Katharine G. I work with these types of assets and Partner With @Alice Horn of Villa Key management. They have the ability to create projections for any property you have an interest in. They build out the Pro-forma for you so you have an idea of what you are getting into. I would be happy to help in any way I can so feel free to reach out. 

    [email protected]407-590-9858
    GPG Team 596 Reviews
    WebsiteView Page
    3Reply
  • Alice Horn
    Property Manager · Kissimmee, FL · Member since 2019 · 445 posts · 266 votes
    5y

    Hi @Katharine G.sounds like a great plan!  Thanks for the shout out @Tyler Gibson. Feel free to PM me and we can help you with your search. As Tyler said, we can help you assess communities, home types and even understand occupancy/revenue projections for individual homes. Have fun with the search!

    0Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    5y

    Thank you, @Tyler Gibson! Followed up with @Alice Horn and looking forward to diving into the search!

    1Reply
  • Joseph James
    Member since 2020 · 20 posts · 6 votes
    5y

    Thread is of interest.  Following. 

    0Reply
  • Fab Ragh
    Rental Property Investor · Bronx, NY · Member since 2019 · 46 posts · 6 votes
    5y

    Something I am currently interested as well.

    4BR/3BA SFH (possibly smaller if the numbers make sense)

    Between Kissimmee & Lake Nona area (not something like pine hills)

    30-45 minutes to Disney & tourist area

    No HOA or low HOA

    Must allow a short term rental (open to long term rental if the numbers make sense)

    Last property I was interested in, I found out that it only allowed 7 month leases for rentals.

    0Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    5y

    Hi all!

    Have spoken with a number of you and am so grateful for the advice. Spoke with some folks who said Disney is oversaturated and don't even try, and others who ensured it was a great investment. Oh boy!

    Favorite communities are:

    Windsor at Westside

    Paradise Palms

    Solterra

    Broadening my budget a bit to 200K-350K, hoping for 4-5 bedrooms with its own pool (open to townhome or SFH.)


    Anyone have strong feelings about these communities? Other things I should be considering?

    6Reply
  • Rachael L.
    Member since 2020 · 9 posts · 0 votes
    5y

    @Katharine G. What made you go against Windsor Hills and Championsgate? Like your original post, I heard most people recommend these two communities. I'm in the same situation with you, looking for STR, hope to share some info with each other.

    0Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    5y

    Hi @Rachael L.! They're both still on my radar for sure, but was honestly a bit underwhelmed by Windsor Hills upon visiting. As I hope to use the unit a bit myself, I also want to take into consideration the kind of community I'd like to use (which, conveniently, is also about to be primary parent demographic so I'm hopeful other millennials will be looking for similar things)

    FWIW, I'm happy to do reno on an individual unit, but was kinda underwhelmed by the community as a whole.

    I liked Champions Gate, but at my price point, I can't buy much that's appealing there.

    0Reply
  • Kristine Eickman
    Investor · Minneapolis, MN · Member since 2011 · 84 posts · 31 votes
    5y
    Originally posted by @Katharine G.:

    Hi all!

    Have spoken with a number of you and am so grateful for the advice. Spoke with some folks who said Disney is oversaturated and don't even try, and others who ensured it was a great investment. Oh boy!

    Favorite communities are:

    Windsor at Westside

    Paradise Palms

    Solterra

    Broadening my budget a bit to 200K-350K, hoping for 4-5 bedrooms with its own pool (open to townhome or SFH.)


    Anyone have strong feelings about these communities? Other things I should be considering?

     I would highly suggest NOT doing Windsor at Westside. Besides the fact that the drive to Disney is brutal, that community in itself has had MAJOR issues with safety and parties over COVID. Someone was just shot and killed last week walking down the street. 

    https://www.wesh.com/article/dozens-of-gunshots-fired-as-deputies-break-up-massive-party-in-kissimmee/34362845#  Article says it was Windsor HIlls, but it was actually Windsor at Westside. 

    https://www.orlandosentinel.co...

    1Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    5y

    Anyone have a preferred lender in the Orlando/Kissimmee area? Or nationwide?

    1Reply
  • Raymond J. RodriguesBusiness Member
    Lender · Miami, FL · Member since 2017 · 1k+ posts · 797 votes
    5y

    @Katharine G. feel free to reach out. 

    [email protected]619-456-8311
    Helm Mortgage Corp.5127 Reviews
    WebsiteView Page
    0Reply
  • Mark Sinclair
    Real Estate Agent · NJ · Member since 2021 · 20 posts · 7 votes
    5y

    @Katharine G. I have a lender in Florida that I have been very happy with. Can give you contact information if you are still looking as I am currently in the very same situation you are in. Looking for both a STR with an added bonus to use for ourselves. Finding it difficult to run numbers and get a solid feel if the condos I'm looking at will generate the interest needed through the year. I have a couple other contacts that have been helpful if you are still looking to speak with people. Just came across this thread as I'm looking for insight as well. It's for sure taken time to look into the different properties that could be available, HOA fees to consider, which ones will allow you to rent out long or short term, etc. I'm not in the market hands on, being in New Jersey, but I have been heavily researching the market recently. Curious about your findings and your process as well. Looking to make a move myself in the very near future, let me know if those contacts would be helpful for you!

    0Reply
  • Alice Horn
    Property Manager · Kissimmee, FL · Member since 2019 · 445 posts · 266 votes
    5y

    @Mark Sinclair in general, we recommend S/F pool homes, or town homes with pools over condos. The Disney market is oversupplied with condos, making it challenging to achieve strong rates during a typical market. (Right now, EVERYTHING is booked solid due to peak season and pent up demand, but that is not always the case). There are a few notable exceptions and we are happy to share our thoughts. PM me if you would like to discuss your options!

    2Reply
  • Mark Sinclair
    Real Estate Agent · NJ · Member since 2021 · 20 posts · 7 votes
    5y

    @Alice Horn it is an interesting point. Some of the higher demand points seem to be in more notable developments, but I do think people are trending towards wanting more space. Certain condo options in the 3/4 bedroom space seem to be doing well consistently on Airbnb with what I have noticed.  

    0Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    5y

    @Mark Sinclair Still haven't found that perfect property just yet--but I have zeroed in on exactly what I want in terms of Bed/bath, which community, private pool, etc. Properties were coming up like crazy in February but it has really slowed over the past couple of weeks--assuming this is largely because so many places are booked so well as @Alice Horn mentioned. (BTW, Alice has consistently been a wonderful font of knowledge!) Trying to remain patient and wait for the right thing until it comes up--though, of course, I could miss low interest rates by that point. If only I had a crystal ball! :) 

    2Reply
  • Mark Sinclair
    Real Estate Agent · NJ · Member since 2021 · 20 posts · 7 votes
    5y

    @Katharine G. Would always be nice to have one of those! Thanks for the tip. For sure seems like a situation where finding the right place is essential. 

    0Reply
  • Kyra Waters
    Rental Property Investor · Youngstown, NY · Member since 2019 · 17 posts · 7 votes
    5y

    @Mark Sinclair and @Katharine G. I too, am new to REI, and love reading all of this advice! We want to use a property ourselves as well. @Mark Sinclair I would love the name of your lender if you are still giving it out.  Analyzing properties is a challenge, hoping you don't forget to add something to the expenses! 

    0Reply
  • Mark Sinclair
    Real Estate Agent · NJ · Member since 2021 · 20 posts · 7 votes
    5y

    @Kyra Waters sure thing! Send me a message and I can give you the contact info.

    0Reply
  • Kyra Waters
    Rental Property Investor · Youngstown, NY · Member since 2019 · 17 posts · 7 votes
    5y

    @Mark Sinclair I'm trying to inbox you but your name isn't coming up, can you inbox me?

    0Reply
  • Jasniry Antelo
    Member since 2021 · 1 post · 0 votes
    5y

    Hi! As an investment opportunity, I am looking at STR options in Championsgate: 3 bedroom condo or townhome option with pool. However, I have doubts about the level of occupation of each unit. Also, when residing outside of Orlando, it would be advisable to take the service of a property manager or there are mixed options that can take care of the publications / reservations and hire a cleaning / maintenance service. I appreciate your suggestions or if you could comment on your experiences. Thank you!

    0Reply
  • Shawn McCormickPro Member
    Realtor · Central Florida-Orlando · Member since 2014 · 1k+ posts · 892 votes
    5y

    Hi @Jasniry Antelo Championsgate has alot of options in both single family and townhomes. Be careful as some parts are zoned for longer stays only (vistas). I would be happy to speak with you about any opportunities in there or a couple other communities with similar amenities and location to Disney that will provide comparable returns.

    Let me know if you would like to talk.

    0Reply
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