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August 4, 2025 • 23 mins

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The vacation rental landscape is transforming before our eyes, with shifts that started during pandemic times now cementing themselves as permanent fixtures in our industry. Hosts Tim Cafferty and Tiffany Edwards dive deep into the most significant trends reshaping how successful property managers operate.

Remote work flexibility has fundamentally altered travel patterns. Though some workers have returned to offices, the ability to work from anywhere remains firmly established. Smart vacation rental managers are capitalizing on this by ensuring properties feature proper workspaces, reliable high-speed WiFi, and marketing that specifically targets these "bleisure" travelers. As Tim notes, even transforming underutilized spaces into dedicated office areas can become a powerful differentiating amenity.

Perhaps most striking is the dramatic shortening of booking windows. Both hosts report seeing timeframes cut in half compared to previous years, with Tim sharing a recent booking made just 24 hours before arrival. This requires a hands-on approach to pricing strategy, adjusting rates for remaining inventory without undervaluing properties. "This isn't a slash sale," Tiffany emphasizes - there must always be a threshold below which prices won't drop.

Today's guests also demand more flexible cancellation terms before committing to bookings. While historically some managers maintained strict policies, both hosts have seen positive results from more guest-friendly approaches. Booking platforms are even incentivizing flexibility through algorithm benefits. The numbers consistently show that despite occasional cancellations, the net result of more flexible policies proves positive.

Communication expectations have similarly evolved, with guests strongly preferring text messaging over phone calls. They want control to initiate contact when convenient while expecting prompt responses. Implementing effective texting systems with personalized automated responses has become essential, though interestingly, proactive welcome calls can still create positive impressions precisely because they're unexpected in today's text-dominated world.

The hosts also discuss how social media influences guest expectations, the strategic use of influencer partnerships, and important new FTC regulations requiring transparent pricing across the vacation rental industry.

These trends aren't temporary - they represent permanent shifts in guest behavior. Success now depends on adapting to meet these evolving expectations. Visit TheVacationRentalKeyWithTNT.com or find us on social media to join the conversation and share your experiences navigating these industry changes.

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Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:10):
You're listening to the Vacation Rental Key with T&T
, the podcast for vacationrental managers by vacation
rental managers.
I'm Tim Cafferty and I managetwo companies, one in Virginia
and one in North Carolina.
I'm one of the two T's.

Speaker 2 (00:26):
And I'm the other, T Tiffany Edwards, born and raised
in the vacation rental business.
I help manage our familybusinesses from Key West all the
way to Kauai.

Speaker 1 (00:36):
In the next 30 minutes, we're going to give you
our keys to success in thevacation rental business.
To success in the vacationrental business.
We're back.
Welcome to August.
Everybody Can't believe it.
It's already here Before youknow it.
Labor Day will be behind us andwe'll be talking about

(00:57):
conferences coming up.
We wowed you last time withamenities that will wow your
guests and we're back to wow youagain this week.
Diff.

Speaker 2 (01:06):
I still am trying to compartmentalize that.
It's August and then theholidays come and we're now at
the end of the year, right?
So I'm excited to get into whatwe've got on the table for
today.
We want to talk about trends.

Speaker 1 (01:21):
There's a lot of trends out there right now.
In fact, we might do a coupleof episodes on trends.
There's a lot of trends outthere right now.
In fact, we might do a coupleof episodes on trends.
There's a lot of trends thissummer that have popped up that
I didn't expect, but generallytrends in the industry.
Maybe you know some of thesealready, maybe these are going
to be new to you, but we've gotsome points here that I think
are worth you listening to andmaybe get a pad and paper.

Speaker 2 (01:42):
Absolutely, and the most important part about these
trends is you probably are aware, but we're going to dive a
little bit deeper on how youaccommodate these trends within
your business and make sure thatyou're capitalizing on them.

Speaker 1 (01:56):
Let's get into it.
We've got what?
I don't even know how manywe've got on here, but I think I
see at least two, three, fourgeneral areas.
And let's start at the top.
And that is a trend thatstarted after COVID Working out
of the office, working at home,we're not in the office as much
as we were as a generalpopulation.
Now, true, people are goingback to the office, but it's

(02:19):
like a genie out of the bottle.
You can't quite put it back theway it was supposed to be, and
so we, as innkeepers andaccommodations professionals,
need to be prepared for that.
What comes to mind on this?

Speaker 2 (02:31):
Tim, it's so important.
Just as you said, it's not likeit was before, where everyone
is working from home.
However, there is a lot offlexibility for people to take
some time to work from home, andyou need to make sure that you
are capitalizing on that.
So one of the ways that youneed to be doing that is all of

(02:53):
your content that you put in foryour listing sites, making sure
that you have information aboutyour high-speed Wi-Fi, you have
pictures about a desk, or youmake sure that you communicate
with your owners that they needto have a space that's available
for a desk and for thathigh-speed Wi-Fi.
You need to make sure youtarget all of that marketing and

(03:14):
that listing content.
The other part, too, that'sreally important we've done this
in the past is that the OTAsreally did a great job of
marketing this sector, this beleisure sector.
So really understanding whatthey're putting out there in
content and trying to replicateit a little bit within your own
system.

Speaker 1 (03:34):
Yeah, and two things come to mind.
One is this is an opportunityfor some recommendations
regarding design components inyour properties.
There's that wasted space thatthe owner doesn't know what to
do with, whether it be a crow'snest at the top of the house or
the room off the living roomthat is kind of a clutter area
of games and puzzles.

(03:55):
They could make it into anoffice area and it becomes an
amenity.
So keep that in mind.
The other thing aboutflexibility I told you my
laboratory is my children.
I have those young workingclass folks out there, including
my son who is an attorney andhe lives in Tennessee.

(04:15):
He works in Kentucky, so hecommutes back and forth and his
employer has allowed him theflexibility to, of course, come
in the office, but at least oneday a week he can work at home
or he could work at the cabin atthe lake if he needed to as
well.
So I think we're finding moreespecially, younger

(04:37):
professionals have moreflexibility where they can get
away for three days and maybecome and visit your vacation
rental property.

Speaker 2 (04:43):
And Tim.
The other thing, too, is thatyou really need to understand
your area.
So if you're in an area thataccommodates smaller conferences
or conferences in general,making sure that you have the
connection and marketing tomarket your properties as a stay
for those individuals who areattending the conference and
maybe bring their family withthem and extend that timeframe

(05:07):
off property from thatconference.
There's a lot of opportunitythere as well, and I know that
for our business out inCalifornia we have a very large
feeder market for Texas.
Well, a lot of thoseindividuals that we market to
like to get out of the Texasheat during the summer and they
have the flexibility to come andstay in California for a month

(05:29):
at a time and work and kind ofgo back and forth.

Speaker 1 (05:33):
Wow, great, I need some of that work.
That's great Me too.
One last point on that as youmarket this bleisure content,
make sure your listings are onpoint.
Pictures are really valuable.
I sense an episode coming inour near future where we look at
some listings and some listingfails One of my favorite things

(05:55):
to do.
Don't be one of those we pickon where you have maybe a
computer in the screen.
You remember that was amenity,like 15 years ago.
It has a computer dear.
Oh, this is wonderful.
No, we don't want that, but wewant a nice workspace.
Make it inviting, make thepictures look good.

Speaker 2 (06:12):
Please don't be the large computers you know from
yesteryear.
It's like the flat not having aflat screen TV.

Speaker 1 (06:18):
Exactly, we used this 10 years ago.
We're not using it anymore.
Let's put it in the rentalhouse.
Oh boy, yeah, okay.
Anything else on the workingfrom home aspect as a trend?

Speaker 2 (06:29):
I will add in your property, making sure that you
have obviously the Wi-Fiinformation in almost every room
framed and up and ready to go.

Speaker 1 (06:39):
Excellent.
Okay, another trend we want totalk about here for a minute is
that immediate satisfaction, forlack of a better wording,
particularly as it relates topricing.
We are seeing shorter bookingwindows.
I know you out there arenodding your head.
People want those last minutedeals.

(06:59):
So what kind of trends do wethink of when we're thinking
about adapting to this, or whatcan we do to adapt to this trend
?
Tiffany?

Speaker 2 (07:09):
that's great, because we're seeing some numbers this
year that I would have neverthought possible.
We're seeing booking windowsfrom last year to this year cut
in half.
I'm seeing booking windowsshrink for our location, hawaii,
which I never thought was thecase, but I think it goes back
to this culture that we have nowof immediate satisfaction.

(07:30):
I want something.
I want to Amazon prime it, Iwant to receive it the same day
or two days later, and so youreally have to be on top of your
rates and adjusting for thoserates.
You really need to market thoseopen two to three day windows
that you may have and I knowthat we've mentioned this in

(07:50):
previous podcasts, but, knowingyour owners that are comfortable
with opening up some of thosewindows, also with some of your
larger homes, if you wannashrink in some of those days and
open up some of those times foryour guests as well, those are
great opportunities and onesthat some of those times for
your guests as well.
Those are great opportunitiesand ones that your guests are
looking for right now.

Speaker 1 (08:11):
Love that and I 100% agree with you.
I have never seen so many lastminute bookings.
Last minute to me is within 30days, but I'm talking.
I had one of my houses bookthis past Saturday for a Sunday
arrival unbelievable.
Somebody made the plan 24 hoursbefore they arrived.

(08:31):
But that's what we're dealingwith and you better make sure
your pricing is available forthose folks that they feel like
they get a good deal on that.
And the other thing don't do itautomated.
Make sure you're in there andyou know what's going on.
Another thought I have on thatis making sure you're
communicating with your propertyowners so that they understand
this trend and they are notweirdos because their house

(08:53):
isn't booked 48 days out.
This is what we're doing, folks, and we need to make sure
everybody is aware and we'rehandling it professionally as
possible.

Speaker 2 (09:01):
Tim, I really think this trend is here to stay.
I really think that it's a bigcultural shift and I think that,
to your point earlier, I thinkit really depends on you being
involved on the pricing and onthe rates, with whoever helps
with your revenue management.
That is going to be key fromthis point forward.

Speaker 1 (09:20):
Do you mind sharing what kind of philosophy are you
thinking on rates?
Is there a certain time framewhere lights go off?
We're green light here.
We get here it's a yellow light.
We get here, it's a yellowlight.
We get here it's a red light.
Do you have a philosophy abouthow you adjust pricing?

Speaker 2 (09:37):
Yeah, that's such a great question.
So I think it all depends onwhat time of the peak season
that it is.
So that is a very largecomponent.
We also weekly go through andwe really drive down to house by
house what's not performingwell.
Before, where it would havebeen two to three weeks out, we
would have been more concerned.

(09:58):
Now we're looking kind of aweek out.
But it also depends on whichcompany.
So there's one company thatwe're more concerned about
occupancy and so we areconsidering daily dropping that
ADR for that occupancy.
So our inventory allows thatFor some of our other properties
we aren't booking or aren'tpressing that red button until

(10:20):
much closer.
So, looking at it more so aweek out and that's based on
that property by property andoverall what we're coming in for
a revenue for the business.

Speaker 1 (10:31):
Yeah, I still can't get over that booking.
I'm not sure I ever will,because I had resigned myself to
the fact that this house wasnot going to get booked for this
week.
This is one of my personalhouses, by the way, so not just
in the inventory, it's my houseand it was one of only three
that weren't booked for the weekand I had already prepared for
my wife.
I hey, we'll have anopportunity, we can go in and
freshen it up and hey, maybe wecan spend a night there.

(10:53):
And then, lo and behold,literally the morning of the
person checking out and thevacancy to start, I get a
message you have a booking and Ijust I'm dumbfounded that
somebody would not plan furtherin advance.
But again, it's a trend.
Better adjust to it in advance.

Speaker 2 (11:13):
But again, it's a trend.
Better adjust to it.
And, tim, the other importantpoint of that, too, is don't
undervalue.
This isn't a slash sale.
You still want to be able todrive financial gain from
whatever this booking is, sodon't cut yourself too far or
too low, and that's reallyimportant for you to understand
when you look at pressing thatred button, because there is a

(11:36):
point that we will not go below.

Speaker 1 (11:38):
Yeah, there's some great tools out there.
We've talked about them before.
Make sure you're watching them.
See what the ADR is doing inthe market.
Make sure you're notundercutting yourself, but make
sure you're letting people knowthat you have availability for
from five properties.
Another thing I think we'reseeing is those folks are
waiting because maybecancellation policies are

(11:59):
driving them and they don't wantto risk it.
What are you seeing oncancellation policy trends?

Speaker 2 (12:04):
That is something that the consumer is looking at
constantly, and we're in thisflux where, especially in our
industry, where so many propertymanagers have a different
cancellation policy than what anAirbnb or what a Vrbo policy
would be.
We've done really well onchanging our cancellation policy

(12:27):
this year to be a little bitmore accommodating towards the
guest.
We've seen a significantincrease in reservations as a
result, but that is definitelycreating a very significant
trend towards finalizingbookings for consumers and for
guests.

Speaker 1 (12:45):
People can blame it on whatever, whether it be the
economy, just the generalnervousness about where they are
in their lives, but they don'twant to risk financial loss.
And I have had to face thisbecause we had the strictest
cancellation policy in my area.
But I see now it's loosening upand Vrbo has some rewards

(13:06):
available to you if you do havethose more flexible cancellation
policies in terms of how youshow up in the algorithm and
that sort of thing.
And they really the guests,they're demanding this.
It's not just that they want it, they're demanding it.

Speaker 2 (13:18):
Yeah, it's another one that's not going away and
it's clearly been adopted by somany in the tourism space and
industry.
And I will say we've ran thenumbers in several businesses
where we've changed ourcancellation policy and we've
just done really well.
As it relates, you're stillgoing to have some that cancel
very close to the time frame.

(13:39):
However, overall, it's still anet positive for us.

Speaker 1 (13:44):
Okay, so there's some trends about bookings and the
immediate satisfaction.
Speaking of immediatesatisfaction, how about the
ability to communicate with ourguests text and social?
What are your thoughts there?

Speaker 2 (13:58):
This is such a good one, another one that is here to
stay.
Text messaging is so importantfor guests.
I think that if you really takea look at yourself, how many
times do you want to be on aphone call and be moved around
from individual to individual orhear any of the waiting music,

(14:19):
and not to say that that'snecessarily your company?
But I just think that overall,we have a shorter fuse for our
guests, especially if there'sany type of issue.
I also think, too, that peopleare wanting to get away and not
be encumbered by a phone ringing, and they want to have the
ability to decide when to answer.
But I think also, when theyhave an issue, they want an

(14:42):
immediate response to send outthat they can control, and so
that texting capability is soimportant to have for your
guests.
Texting capability is soimportant to have for your
guests, whether that be throughsomething that you use
internally throughout youroffice.
We use a software.
It's vital for us, it goesthrough and it keeps all of that

(15:03):
information for our staff.
But I like to think of it, too,as text messages and
information that you can haveavailable by a text is similar
to what they would see on awebsite or add-ons.
I still don't think it replaceslike a welcome.
How are you to the area, calland maybe leaving a message, but

(15:24):
other than that, everythingneeds to be a text capability.

Speaker 1 (15:28):
Agree completely.
I had experienced this pastweekend that I just was thinking
of, as you were describing that, where I was monitoring the
texting.
As I came in early in themorning I was the only one in
here and so the person hadcomplained about garbage pickup.
It wasn't done and I apologizedand I did the A train agree,

(15:48):
apologize and act.
We're so sorry.
I agree the trash shouldn't bepiled up.
We will get someone by thereand the person responded back.
Have you not seen the string ofmessages that I've left on this
?
And I scrolled back and sawthat she had texted four times
overnight.
Well, nobody saw the messages.
Sorry, didn't check my messagesat 2 44 AM, but we're here now.

(16:12):
This goes back to the immediacything.
Again, people want to know youare standing by and ready to
solve whatever problems theyhave.

Speaker 2 (16:20):
And even further on that.
Tim, you still need to makesure that if you have an
automated response, that it'svery personable, yes, and it
doesn't read like a chat GPT.
So that's really important too,so that if it does come after
hours and you do have anautomate, you still make them
feel warm and fuzzy.

Speaker 1 (16:39):
I love the idea of that call it kind of reverses
where you were talking aboutgetting lost in that maze which
I'm sitting here dreading.
I know I have to call SpectrumCable and I know I'm going to be
on the phone for an hour.
I have no idea where in theworld I'm going to end up, but I
can't get it done via text oron the computer so I have to
call them.
So I'm dreading that.

(17:00):
But the interesting twist thatyou just threw in there is that
a welcome phone call is apleasant surprise.
It's an actual human welcomingme.
I'm not pissed off that myphone's ringing.
Why don't you just text me?
Oh, I'm here from XYZ Realtyand I want to make sure you know
that we appreciate you beinghere.

Speaker 2 (17:20):
What a great idea.
Proactive versus reactive, andso then, even moving on the
influence of social media,texting technology I think this
trend is also here to stay, andthat is the overall influence of
social media and, what I liketo think of, of the social
jealousy, so all thoseinfluencers who like to post in

(17:42):
your area of these idyllicvacations and create a lot of
jealousy for anyone else who'snot on this trip.
That is something that you wantto also look at trying to
recreate.

Speaker 1 (17:56):
My former co-host, Sarah Bradford, shouted to her.
She used to call it thatInstagram moment.
Do you have an Instagram momentat your property?
I just built one in front ofour office.
We have this beautiful newstallion that's bedazzled in
reflective tile and I've alreadyseen like it's been unveiled
for five days I think it is now.
I've seen probably 10 peoplestop and take a picture in front

(18:19):
of our stallion.
Look at this idyllic situationI am in.

Speaker 2 (18:22):
Look at me, look at what I'm doing yes and you're
not and you're not.
And the other part about that,too, is really making sure, when
you're developing yourmarketing plan, how much are you
utilizing influencers andmaking sure that you target
influencers that really are thedemographic of your feeder

(18:44):
markets and your company.
I know, and Tim, you probablyget this all the time of people
who say, oh, I'd love to come,I'm happy, I'm happy to come and
stay at one of your propertiesand post three times.
Well, my next door neighbor hasmore followers than you.
I'd rather have them stay there.
So it's really driving in whatinfluencer you're trying to

(19:08):
target, what influencer, whatthey can create and the content
and how much activity they haveon their profile and within
their account, and reallycultivating that trip with that
influencer, because that'sreally important as well.

Speaker 1 (19:25):
Yeah, our local visitors bureau does a good job
with that of making sure, whenthose high-profile people come
to town, that they do havethings to do and they'll
actually offer it.
Hey, we have this person andthis is their profile and this
is what they're reaching.
Would you be interested inhosting them?
I love that part of it, insteadof me having to do the research
and a wish and a hope, as weused to say back in the day.

(19:46):
One other trend I think we needto touch on here and that is
related to us as individualinnkeepers.
I've used that word a lot herein the last month or so.
Individual innkeepers I've usedthat word a lot here in the
last month or so.
There's a trend.
It's a law on the ConsumerProtection Agency about

(20:06):
transparent pricing.
I don't know that everybody'son board with this yet.
Tiffany, the fee disclosurething we all go to the hotels
and they charge us that resortfee and we'd all get PO'd about
it.
Well, they did something aboutit, but they also extended it to
us as well.
We need to make sure we'retransparent in our pricing on
our websites and so on.
Right.

Speaker 2 (20:23):
Absolutely so.
This law was passed back in Mayof this year, 2025.
And I don't think a lot ofpeople are aware of it, but for
the first time, the short-termvacation rental industry was
included in a full hospitality.
The short-term vacation rentalindustry was included in a full
hospitality ticket salesexperience decision from the FTC
, and so it is extremelyimportant that you disclose what

(20:46):
your fees are, that you arefollowing along with what the
Federal Trade Commission has putout and requested, and I think
that overall consumertransparency is going to be a
very important part of what itis that we do, because it's not
because of us specifically, butoverall of the industry.

(21:07):
There's just been so muchconsumer backlash of here's my
rent and then when you go to theend and you probably more
specifically, we could use, as ahotel, $40 a night for that to
leave your car, $20 a day forWi-Fi, whatever it may be, we're
going to be lumped into that aswell.
So you need to be making surethat you're aware of that FTC

(21:29):
decision and then also thatyou're following compliance.

Speaker 1 (21:32):
I was very pleasantly surprised to see the majority
of my competitors and us here inthis market are compliant on
this, but the ones that aren'tstick out like a sore thumb.
Now You're not doing it right,so make sure you're doing it
right.

Speaker 2 (21:47):
And Tim.
The other thing for that, too,is that you then look like
you're trying to hide some ofyour costs.
So even if a guest, when theylook at your site, doesn't
understand that this is actuallyfederal regulation, you look
like you're hiding a bunch ofinformation, as opposed to

(22:07):
having a site that has it listedout.

Speaker 1 (22:10):
Yep Can be a competitive advantage.
Make sure you get on board withthat.
Okay, any other trends we needto talk about here?

Speaker 2 (22:16):
Those are the ones when we look at trends here in
the last several years.
These are the ones to me.
They are not going away.
So, as Tim said, if you haveyour paper and pencil, make sure
you write some of these down,because they're not changing.

Speaker 1 (22:32):
Gave you some more keys to the vacation rental
industry and hope that youenjoyed that.
We'll be back next time.
Maybe we can talk about sometrends for this summer.
I've got some in mind.
It's been a rough one.

Speaker 2 (22:46):
Me too, tim.
As we said earlier.
I'm surprised that it's August,but I have just a tad bit of
PTSD.
So maybe on the next episode wecan share what we've learned.

Speaker 1 (22:58):
Oh, that's always healthy.
Okay, Well, until next time,folks.
I hope you enjoyed this one.
We'll look forward to seeingyou on our website,
TheVacationRentalKeyWithTNTcom,or look us up on social.
Send us a message there andgive us a review.
It helps.
I appreciate all that you dofor us and we will be back to do

(23:19):
it for you again next time.

Speaker 2 (23:21):
So long, everybody.
Bye guys, Thanks for listening.
We'll see you next time.
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