Looking at short term rentals for the first time. Need advice

Looking at short term rentals for the first time. Need advice

Homeowner · Hendersonville, TN · Member since 2008 · 68 posts · 7 votes

I have have had 2 long term rental properties for about 10 years.  Now I am considering a short term rental in an area like Florida or Gulf Shores, AL.   I would like to be able to use it when it is not rented.  I was a bit turned off when looking at condominium fees and other expenses, but then remembered I may be able to deduct these on my taxes.

I would be living in Tennessee and would need the property managed.  Are there property managers who specialize in handling short term rentals like this?  I would like to know what I would be getting myself in to. What costs to expect.

I am sorry for such a newbie question.  Even if you just had a link to where I could read about this it would be appreciated.



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Travis TimmonsPro Member
Rental Property Investor · Ellsworth, ME · Member since 2021 · 1k+ posts · 2k+ votes
2y

It's tough out there. We invest in a market that is a couple years behind the rest of the country (Downeast Maine), and even there, it's hard to make anything on the MLS pencil out unless you want to take on a renovation project.

I can't speak for Florida Gulf Coast or Gulf Shores, but my guess is that it would be very difficult get more than a meager cash on cash return if self managing. If you are hiring a property manager, I don't see a path to profitability for the first few years. I may be missing something bc I don't invest in those markets. 

You need to decide if you want a vacation home or an investment. Every situation is different, and subsidizing your family vacations would be a very worthwhile use of your money if you have a good income and don't care if you lose $10-30k a year to hold on to a $500k-1M asset that will appreciate over time. I'm making those numbers up for example's sake, but you get the idea.

We've launched short term rentals from 2000+ miles away (and self manage). Feel free to send me a DM if you think that I can be helpful. We've all been there. I'd be happy to answer any questions and have nothing to sell. 

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  • Candace PfabBusiness Member
    Realtor · Orange Beach AL · Member since 2018 · 150 posts · 125 votes
    2y
    Quote from @January Johnson:
    Quote from @Candace Pfab:

    Exactly.  STRs require more management - 1 to 2 new guests per week which involves managing 50-100 guests per year, marketing the property, managing bookings, guest communication, scheduling cleaners, higher level of maintenance (think lightbulb changes, battery changes, comforter changes, parking passes), etc.  A good property manager is worth their weight in gold, but we also have about half of our clients self-managing for bigger tax advantages like cost segregation and those who enjoy the process.  There are also some co-host models here where someone might handle part of the process for you at a reduced fee.  You just have to find the best fit for you.  


    A good property manager is going to cost you any gold you would have made. 
    ;  )


    I understand, but self management is not for everyone!  We have both types of clients, so I think it is important for buyers to understand their options and what will fit their life/goals the best :)

  • Real Estate Agent · Member since 2019 · 569 posts · 257 votes
    2y
    Quote from @Steve Maye:

    I have have had 2 long term rental properties for about 10 years.  Now I am considering a short term rental in an area like Florida or Gulf Shores, AL.   I would like to be able to use it when it is not rented.  I was a bit turned off when looking at condominium fees and other expenses, but then remembered I may be able to deduct these on my taxes.

    I would be living in Tennessee and would need the property managed.  Are there property managers who specialize in handling short term rentals like this?  I would like to know what I would be getting myself in to. What costs to expect.

    I am sorry for such a newbie question.  Even if you just had a link to where I could read about this it would be appreciated.




     We have one in Gulf Highlands that is 958 a quarter which includes 11 pools, tennis courts, pickleball courts, deeded beach access, restaurant on site, goofy golf and other amenities. You can find options under 350k that can do 40k plus on rental income. Currently our unit is at 95% occupancy for the last quarter. 

  • Real Estate Broker · Cape Coral, FL · Member since 2014 · 382 posts · 300 votes
    2y

    @Steve Maye

    Hi Steve,

    I've represented many STR buyers here in SW Florida and most of them use professional property management to take the reigns, soups to nuts. But some PM's will allow you to use an a-la-cart approach where you're responsible for some tasks and they do the rest. For example, I have one client who chose to do some of the "back office" tasks such as managing the bookings through Airbnb, and hiring the PM to handle more of the on-site responsibilities, for a discounted rate.

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