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. 

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  • Andrew C.
    Investor · Forest Hills, NY · Member since 2014 · 101 posts · 52 votes
    5y

    @Katharine G. Just curious why you found Windsor Hills underwhelming.  I was interested in that community and heard good things, mainly proximity to Disney and amenities.  Based only on pictures and amenities listed, it seems like a perfect place for families...water slides/splash zone/zero entry pool, etc.  I was looking at it a year or two ago but decided to invest in something else...and looked back and the prices have appreciated a lot!

    1Reply
  • Ted Caputo
    New to Real Estate · Lancaster County, SC · Member since 2021 · 32 posts · 12 votes
    5y
    @Katharine G.:
    I was reading through this thread hoping to find that you purchased in the end. I too am looking in the Orlando area. I'm a lifelong New Yorker that is relocating to South Carolina and intend to invest in real estate.

    I have been in contact with @Alice Horn and she and her team have been terrific to deal with. I hope we can put a deal together.
    1Reply
  • Alice Horn
    Property Manager · Kissimmee, FL · Member since 2019 · 446 posts · 266 votes
    5y

    Thanks for the kind words, @Ted Caputo! Hope all is going well with your relocation.

    @Andrew C., Windsor Hills ticks all the boxes for many families! But it is an older resort, so if someone is looking for newer build homes, it’s not for them. Personally, I like that it’s a bit more spread out and the views from the pool areas are very nice. The resort has a welcoming feel…but very few homes for sale at the moment!

    0Reply
  • Andrew C.
    Investor · Forest Hills, NY · Member since 2014 · 101 posts · 52 votes
    5y

    @Alice Horn Yes, very few homes and prices have gone up dramatically since I was looking 2 years ago.  At the time, I was considering the 3/3 Townhouses.  Do you think the larger homes offer a higher return?  

    0Reply
  • Alice Horn
    Property Manager · Kissimmee, FL · Member since 2019 · 446 posts · 266 votes
    5y

    @Andrew C. absolutely! Typically, pool homes or town homes with 4 bedrooms up will perform much better. Feel free to send us any listings you’re considering and we’ll run the analytics!

    1Reply
  • Cody Z.
    Real Estate Agent · Belmar, NJ · Member since 2017 · 370 posts · 200 votes
    5y
    Originally posted by @Amanda Ferguson:

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

    Just curious how you have been liking the Destin market? I am interested in that section of FL but I understand the next few months will be rather slow so it might not be a good time to snatch something up.

    1Reply
  • Matt "Roar" Gardner
    Real Estate Agent · Tampa, FL · Member since 2018 · 464 posts · 452 votes
    5y

    @Cody Z. - As a realtor and investor in the Destin area, we do typically see a slight rise in inventory as we enter the off-season in the end of August. Who knows what is typical anymore though! lol

    Our high season really extended into October last year; however, I don't anticipate that to be the case again this year.

    Good luck in your search!

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

    Hi all!

    So, while I did end up putting in one offer, I didn’t get it and am not currently actively pursuing this market at the moment. Back when I first started looking in early Feb, prices for the exact type of townhome I was looking for have jumped 50K, and it just isn’t feasible for me at the moment. They’re still on the radar, but unless there’s a dip of some kind, that’s not my move for now. Ended up buying a property in the Catskills and will be restocking pennies for a FL property next.

    re: Windsor Hills, it ultimately just felt a bit run down to me. It’s fine enough and had a great rep, but if my fellow millennials (and parents) have the same preference for a more updated look, they’re going to prefer some of the newer communities. But again, it’s still a solid investment! 

    Hope everyone finds what they’re looking for!

    2Reply
  • Andrew C.
    Investor · Forest Hills, NY · Member since 2014 · 101 posts · 52 votes
    5y

    Congrats on the property in the Catskills @Katharine G.!  I was thinking about looking up in the Catskills as well as the Poconos so that I could get some personal use out of it too.  It seemed like the market up there was really hot with a lot of those in the city buying up places due to the pandemic.  Are you self-managing or you have a property manager?  What are the main activities that attract guests up there...hiking, skiing in the winter?  I have STRs in Buffalo/Niagara but that's far upstate and not something I could do for a weekend trip =)

    0Reply
  • Russell Grevler
    Property Manager · Catskills · Member since 2020 · 38 posts · 17 votes
    5y

    @Andrew C. @Katharine G. I own and also manage a few properties in Roxbury/Margaretville as well as Stamford areas. Let me know if you’re interested to find out more information about the area as well as the main attractions!

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

    @Andrew C. from what I’m finding, the market is hot pretty much everywhere! I put an offer in upstate the same day I offered in Florida—both slightly under asking. NY panned out, FL didn’t—and sort of just trusted fate.

    I’ve long been in love with Hudson Valley/Catskills—SO much is way overpriced right now, but there are pockets I feel strongly are up-and-coming/not overpriced just yet. I got a house at what I feel is a super fair price with lots of opportunity. Pluses up there are obviously Manhattan weekenders *and* folks moving up there in droves wanting to try it out, skiing if you’re near Hunter/Windham, and all the great towns dotting the Hudson River. 

    Still have Florida dreams, just holding off for now.

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

    Scratch that--just looked and the units I was looking at in February in Orlando are now 100K over what they were then. Insanity!

    1Reply
  • John Thedford
    Real Estate Broker · Naples, FL · Member since 2013 · 9k+ posts · 6k+ votes
    5y

    @Katharine G. and tomorrow another 5K! 

    0Reply
  • Xiaoshuang Zhang
    Member since 2021 · 3 posts · 1 vote
    5y

    For windsor hills, I found the community itself to be very nice, especially the pool area, slides section was a huge hit with the kids (a mini water park). But the homes themselves could be old, so when you buy a home, look for updated ones. I was very impressed with their security, they were so strict. Generally it felt like a well run establishment. And yes the recent security issue in Westside and Windsor hills proximity to disney tipped me to buy in windsor hills. Also $/sqft westside was cheaper even though the homes are much newer

    1Reply
  • Kenneth D'Souza
    Member since 2022 · 2 posts · 0 votes
    4y

    Did You finally buy a place @Katharine G.? Any advice for a first-time investor? Any areas that you have zeroed in on? Any realtors, or property managers that you recommend?

    0Reply
  • Shawn McCormickPro Member
    Realtor · Central Florida-Orlando · Member since 2014 · 1k+ posts · 892 votes
    4y

    Hi @Kenneth D'Souza looking for advice in the STR arena, or in general? Plenty of info and data on Orlando and what communities do well and ones to avoid for the STR communities. The market has shifted dramatically since this post and prices are (hopefully) at a peak, but demand is still very strong. If there are specific questions you have, lots of help from locals here in Orlando.

    1Reply
  • Kenneth D'Souza
    Member since 2022 · 2 posts · 0 votes
    4y

    Hello@Shawn McCormick looking at actually buying a property in the Orlando or Kissimmee area. Just doing some groundwork as to what areas I should look at to buy and what are the different property management companies that I should look at. I was told to buy a place and just put it on Airbnb as many people seem to be getting a decent ROI on their investment.

    0Reply
  • Alice Horn
    Property Manager · Kissimmee, FL · Member since 2019 · 446 posts · 266 votes
    4y
    Quote from @Kenneth D'Souza:

    Hello@Shawn McCormick looking at actually buying a property in the Orlando or Kissimmee area. Just doing some groundwork as to what areas I should look at to buy and what are the different property management companies that I should look at. I was told to buy a place and just put it on Airbnb as many people seem to be getting a decent ROI on their investment.


    0Reply
  • Alice Horn
    Property Manager · Kissimmee, FL · Member since 2019 · 446 posts · 266 votes
    4y

    Sorry, meant to post reply above. @Kenneth D'Souza, the Kissimmee/Davenport/Orlando market offers a large array of purpose-built vacation rental communities with resort amenities. They range from Windsor Hills which is older and closer to Disney; to newer communities like Championsgate, Solara and Windsor Island which are a bit further from Disney but they have larger homes and fantastic resort amenities which make them appealing to guests. Happy to chat about the various resorts, home types and help you compare ROI.

    0Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    4y

    Hey @Kenneth D'Souza! Still on the hunt. Prices have skyrocketed since I started my search, now interest rates rising of course but prices haven't really dropped accordingly, *and* a little nervous about the Reedy Creek impact on property taxes. Wondering if there's any point in looking West towards the Clermont area, but nervous about regulations. Will keep digging! Best of luck in your search!

    0Reply
  • David Vanlandingham
    Investor · Orlando FL · Member since 2022 · 42 posts · 42 votes
    4y

    Clermont is primarily in Lake county. If anything people may be moving to Clermont to get away from Orange County property tax hikes. I live 2 miles from Clermont. 

    1Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    4y

    @David Vanlandingham that was the thought! Are you implying it’s a bad idea due to competition reasons?

    0Reply
  • David Vanlandingham
    Investor · Orlando FL · Member since 2022 · 42 posts · 42 votes
    4y

    No, not at all!  Clermont, Davenport and Groveland are exactly where you should be looking.  Lake County has lower property taxes as well.  Winter Garden, where I live is becoming very expensive but those other areas IMO the timing is right, as in right now!  Google - clermont florida airbnb game house

    Cape Coral is another hot area as well and there are a few other jewels in SWFL.

    2Reply
  • Katharine G.
    OP
    New York, NY · Member since 2018 · 30 posts · 25 votes
    4y

    @David Vanlandingham thank you! I know Davenport is STR friendly—do you know about Clermont (looks like there's regulation but not necessarily restriction?) and Groveland's policies?

    1Reply
  • David Vanlandingham
    Investor · Orlando FL · Member since 2022 · 42 posts · 42 votes
    4y

    Pretty laid back as of now.  I think they are quietly open to Airbnb vs a sf rental property. Lake county school system is overloaded. 

    0Reply
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