All Episodes

March 11, 2025 13 mins

Scott Safford's journey from accidental hotelier to vacation rental maven embodies the resilient spirit of Fort Myers Beach. When his wife purchased a distressed property with a vision, they transformed it into a boutique hotel guided by a simple philosophy: "clean rooms and happy guests." This approach worked so well that neighbors began asking Scott to manage their properties too, organically growing into Sea Gypsy Vacation Rentals – now the largest family-owned vacation rental company on the island.

The path hasn't been easy. Hurricane Ian destroyed Scott's original hotel and much of his rental inventory, following years of challenges including Hurricane Irma, red tide, and the pandemic. Yet throughout our conversation, his optimism and dedication to rebuilding shine through. Scott provides remarkable insight into how Fort Myers Beach is transforming after these successive disasters, countering misconceptions about the island's recovery. With 40-50 bars and restaurants already operational and major developments like Margaritaville driving economic renewal, the community is experiencing an exciting renaissance.

What makes Scott's approach special is his commitment to creating experiences, not just accommodations. He treats guests like they're staying at his own home, offering personalized recommendations for everything from charter captains to menu selections at local restaurants. This level of service has helped him build a diverse inventory ranging from downtown apartments to sprawling beachfront houses that accommodate everything from couples' getaways to family reunions. As Scott perfectly captures it, "The vibe is alive here in Fort Myers Beach." Whether you're a longtime visitor or considering your first trip, now represents a unique opportunity to witness and participate in the island's remarkable rebirth. Ready to experience it yourself? Visit seagypsyvacation.com or call 239-463-0078 to plan your stay.

Sea Gypsy Vacation Rentals 

Scott Safford

(239) 463-0078

info@gypsyvacation.com

seagypsyvacationrentals.com

Send us a text

Mark as Played
Transcript

Episode Transcript

Available transcripts are automatically generated. Complete accuracy is not guaranteed.
Speaker 1 (00:00):
This is the.

Speaker 2 (00:01):
Good Neighbor.

Speaker 1 (00:02):
Podcast, the place where local businesses and
neighbors come together.
Here's your host, cabo, jimSchaller.

Speaker 3 (00:12):
Welcome Good Neighbors to episode number 238
of the Good Neighbor Podcast.
Today we have Good NeighborScott Safford from the Sea Gypsy
Vacation Rentals Welcome.

Speaker 2 (00:22):
Thank you.
Thank you for having me Welcome, good morning.

Speaker 3 (00:25):
Absolutely Always a pleasure to get to know people
in the community and share theirstory with our listeners.
So obviously you're down inFort Myers Beach why?
Don't you share a little bitabout what you do.

Speaker 2 (00:36):
First, Well, right now, what we do is we're
recovering from Hurricane Ianand the last two hurricanes, but
I own Sea Gypsy VacationRentals, which is the largest
family-owned vacation rentalcompany on the island, and we
started about 12 years ago witha small boutique hotel called
the Sea Gypsy Inn my wife and Iand it morphed into a vacation

(00:59):
rental company.
After the hurricane, we lostour hotel.
We lost most of our inventoryvacation rental wise, but we're
rebuilding and building businessback, so I'm excited to be here
.

Speaker 3 (01:13):
It's been quite the journey, so let's take that
journey back a step.
How did you get involved inthis in the first place?

Speaker 2 (01:28):
Well, about 15 years ago, my wife and I became empty
nesters and we were looking fora house on Fort Myers beach.
We had a little little cottage,but we were looking for a
little bit bigger home.
And my wife came home and saidI think I bought a hotel.
And I said what?
So she took me down there andit wasn't a hotel, it was a
distressed property.
But she had a vision and shesaw it and, even though I think

(01:49):
she's still crazy, we fixed itup and started a little boutique
hotel and it was going well forabout five years.
And then one of my neighborscommented that he always sees
cars in our parking lot.
How can we be full all the time?
And I explained to him well,our motto is clean rooms and
happy guests.

(02:09):
And he said, well, I've gotthis apartment I can't rent for
anything.
And I said, well, let me gotake a look at it.
And it had bad furniture,wasn't clean.
And I explained to him look,you have to have nice stuff.
I mean, mean you have to have anice product that everybody
would will enjoy.
And he said, no, no, it's onthe beach.

(02:29):
I said, well, tell you what?
Give me some money, let me fixit up and I'll put it on the
airbnb.
Let's see.
See what happens.
And the very next day that we,the very day that we opened, I,
I, I had it booked and I had itbooked solid, and he told a
friend, he told another friendand all of a sudden I had a
vacation rental company.
So that's how it works.

(02:50):
Yeah, that's how it works.

Speaker 3 (02:53):
But when you're good at something right.
It just evolves.

Speaker 2 (02:58):
Yeah, so what we try to do, besides having clean
rooms and happy guests, is wetreat every guest like they're
staying at our house.
We, you know.
We tell them what, what chartercabinets you use what, what
bars and restaurants to go to,what to order at those bars and
restaurants.
So we try to, you know.
Or if they're playing golf, wetell them what golf courses to
play.
We, you know.
So we, we try to make theirexperience just like they'd be

(03:21):
staying with us.
So that's kind of how we dobusiness and that's part of it.
Yeah, we just, we just focus onfort myers beach, lovers key,
san carlos island.
I mean we, we know all thevendors, we know all the
restaurants, we, we, we can makeit a more than just a vacation.
We can make an experience forpeople based on what their,

(03:43):
their wants and needs are.

Speaker 3 (03:45):
And it comes down to that customer service that so
many businesses nowadays arelacking.
You know, I think a lot ofpeople have forgotten what
customer service is, so it'sgood to see people like yourself
actually practicing it.

Speaker 2 (03:57):
Thank you, and you know it's really tough right now
.
You know this isn't a five starSt Bart's vacation down here, I
mean.
But if you let people know thatwe're rebuilding, there's a lot
of construction going on, noteverything's open.
If you let people know thatahead of time, then you know

(04:18):
they can make the decisionwhether to come down or not.
And when they do come down,it's a unique opportunity to see
an island rebuilding after adevastating storm and you know
they can sense the vibe of theisland, of the business owners,
of the people.
You know it's quite a uniqueexperience for people.
Now it's not for everybody, butfor the people that want to

(04:41):
give it a shot.
I think most people are happy.

Speaker 3 (04:45):
That is.
You mentioned that vibe.
That's the important thing.
It's still there and it's kindof exciting seeing what's coming
, you know, and changing anddeveloping.
So I want to talk aboutchallenges.
Not everything's perfect.

Speaker 1 (05:00):
Even our really really nice houses they still
have.

Speaker 2 (05:15):
you know, the neighbor's fence might be down
or the other side of the housemay have construction, so
nothing's perfect.
So that's the challenge ismaking sure people are happy.
You know, we communicate withguests after they check in, make
sure everything's okay.
So we, you know we do our bestto make sure that people are
happy.
That's, that's the main thing.

Speaker 3 (05:36):
And so let's talk about myths or misconceptions,
whether it's the state of theisland right now or the fact
that you're a small boutiquehotel compared to a large resort
.

Speaker 2 (05:48):
Well, we, we actually we had the boutique hotel and
we lost it in the storm.
So we have actually we haveeverything from one bedroom
apartments downtown to ninebedroom houses on the beach.
So whatever your vacation needsare whether it's one couple,
two couples, a whole family, afamily reunion we can usually

(06:08):
accommodate you.
So that's kind of nice that ourinventory is so diverse.
But one of the bigmisconceptions about the island
is that it's not rebuilt at all.
It's still massive devastation.
It's just not true.
I mean, we're sure it's notperfect, but there's still, like

(06:32):
I said, a vibe.
There's still 40 or 50 bars andrestaurants open.
There are a couple of hugehotels.
Margaritaville helpstremendously.
We're coming back.

Speaker 3 (06:46):
That's the important thing.
You mentioned Margaritaville.
At first everybody was againstit, like no, we don't want that
big part of it, but it's been apart of a staple of the
rebuilding of Fort Myers Beachand a centerpiece drive us

(07:10):
forward.

Speaker 2 (07:10):
I mean, you know, not , it's not for everybody, but I
think people go over there andthey they check it out and some
people love it and they want tostay there and that's great.
Other people, you know, that'sjust not not their deal.
But you know they have so manynice bars and restaurants in
there.
The staff is really friendly.
The pool is fantastic.
We have a lot of our guestsstay with us and they decide to
go down to Martin Reedaville forthe day to hang out at the pool

(07:32):
.
So it's really helped theeconomy here on the beach for
sure.

Speaker 3 (07:38):
Absolutely, and, like you mentioned, it attracts
whatever it's doing, but it'sattracting new people to the
beach and exposing them, givingother businesses opportunities
to branch out a little bit.

Speaker 2 (07:49):
Right and that's one of the hard parts with our
business is we had so manyrepeat customers and after we
had Red Tide we had HurricaneIrma, then Red Tide, then we had
the pandemic and then we hadHurricane Ian.
So we lost a lot of thosegenerational families that came
down year after year after year.
So we're starting pretty muchover, starting anew.

(08:13):
Now we have the diehards thatjust love Fort Myers Beach and
they want to support thecommunity and help out.
But we're starting to get a lotof new families, new people
coming down here, and I thinkMargaritaville is one of the
draws.
Most people that live on thisIsland came over that bridge.
They stayed at a place and theycame back and then they decide,

(08:35):
hey, I might you know, comedown here even longer and then
they buy a home and all of asudden they're they're residents
and business owners.
That's kind of the cycle oflife here on the beach.

Speaker 3 (08:45):
Absolutely so.
Talking about that, do you know?

Speaker 2 (08:54):
obviously a lot has changed, but do you notice?

Speaker 3 (08:57):
anything trending currently as far as what Cabo.

Speaker 2 (09:03):
As far as the type of people that are coming or the
type of opportunities peoplehave here.
Yeah, there's the type of.
What's interesting is the Idon't want to say I would say
that the people coming down herehave more money than in the
past.
There's a lot of people comingdown looking to invest and the

(09:27):
demographic is late 40s, early50s.
They have their eye on retiringin about five to 10 years and
they have money.
So it's really different Now.
It's not different.
Now.
It's not Naples, it's notSanibel, but you know, one of
the things about Fort Myersbeach was oh it's, it's a little
lower income, but it's not thecase anymore.

(09:47):
There's a lot of people with alot of money coming down here
and what's what's cool about itis they're they're not stuck up,
they're not snobby.
I I mean, great thing about thebeach is you can go into any
bar, restaurant and you have noidea what people do, what, how
much money they have and nobodyreally cares.
But what I'm seeing is thatthere's more people now with

(10:09):
more money.
Does that make sense?

Speaker 3 (10:11):
yeah, no, and I always mention when I since
moving down here, I call itquiet money you know, people
aren't flashy with it, butthey're, you know they they're
obviously have a good wealth,but they don't bring it back.

Speaker 2 (10:24):
Yeah, it's that millionaire next door, that
Midwest money.
You know nobody's flashy,nobody.
I mean same thing on the islandEverybody drives Jeeps.
You know, nobody has a superduper expensive car.
I mean you get trashed anywayswith the salt, but nobody,
nobody needs to showboatanything you know, absolutely.

Speaker 3 (10:43):
Just be yourself speaking about the midwest.
I'm from the midwest originallyI am too.
Where are you from?

Speaker 2 (10:49):
milwaukee right outside milwaukee okay, all
right.

Speaker 3 (10:52):
What brought you down to southwest florida?

Speaker 2 (10:55):
my wife my wife's from my wife's from cleveland
she was homeschooled here on thebeach and, um, you know she
just loves this place and thefirst time I came down here I
fell in love with it too.
So, it's, it's just, it's justhome.
I mean, we travel quite a bit,but we always, we always come
back here and, uh, it's justspecial place and it's really

(11:19):
cool now that we're rebuilding,so we have the unique
opportunity to, you know, helpcreate what this Island can be
in the future.
So it's, it's really neat.

Speaker 3 (11:31):
Yeah, it's a.
It's a wonderful opportunity.
You know, through through thecircumstances we've all been
through the last number of years.
So, yeah, I know you've got alot on your plate, but when you
do get a moment of free time,what do you enjoy doing outside
of work?

Speaker 2 (11:47):
I'm in a golf league, keep my sanity.
I take Thursdays off.
Good group of friends I'vestarted about 10 years ago and
it was mostly the businessowners and it seemed like
Thursday was always a good, goodday to get off island.
And it's morphed into more thanjust business owners.
I try to get on my boat as muchas possible but it's been tough

(12:08):
.
We're deep in the heart ofseason right now, so we're you
know we're we're working everyday.
So in off season we my wife andI enjoy to trap, we enjoy
traveling, but it's been toughto to get away from here because
there's so much going on yep,yeah.

Speaker 3 (12:28):
So much to do, absolutely so.
Is there one thing you wish ourlisteners knew about sea gypsy,
that maybe they're not toofamiliar with?

Speaker 2 (12:36):
well, I want people to know that the beach is open
and if, if, for for the localcommunity.
If you have friends coming intotown, come on down to the beach
beach for a staycation, um, orif you just live here, the beach
is open and we have a lot ofrentals that are nightly two
nights, three nights.
So just come up, come on downfor a staycation, we're open and

(12:57):
love to show you how greatthree night.
So just come on down for astaycation, we're open and love
to show you how great it is.

Speaker 3 (13:01):
So how about our listeners go about contacting
you if they wanted to learn moreor wanted to come visit?

Speaker 2 (13:06):
So they can visit our website at gypsyvacation.
com, or give us a call at239-463-0078, or check out our
Facebook and Instagram pages.

Speaker 3 (13:18):
Very good, any last words for our listeners today.

Speaker 2 (13:22):
Just keep, just remember that the vibe is alive
here in Fort Myers beach.

Speaker 3 (13:27):
I love that.
I love that, scott, it's been apleasure getting to know you.
Thank you for being such a goodneighbor and we hope to see you
out at the beach soon.

Speaker 2 (13:35):
Thanks for having me and hope to see you on the beach
.

Speaker 1 (13:38):
Thank you for listening to the Good Neighbor
Podcast.
To nominate your favorite localbusinesses to be featured on
the show, go to GNP Estero.
com.
That's GNP Estero.
com, or call 296-2621.
Advertise With Us

Popular Podcasts

40s and Free Agents: NFL Draft Season
Dateline NBC

Dateline NBC

Current and classic episodes, featuring compelling true-crime mysteries, powerful documentaries and in-depth investigations. Follow now to get the latest episodes of Dateline NBC completely free, or subscribe to Dateline Premium for ad-free listening and exclusive bonus content: DatelinePremium.com

The Bobby Bones Show

The Bobby Bones Show

Listen to 'The Bobby Bones Show' by downloading the daily full replay.

Music, radio and podcasts, all free. Listen online or download the iHeart App.

Connect

© 2025 iHeartMedia, Inc.