April 22, 2026

Wintering in Spain 2025 – Estepona #1 … Booking a Place on the Costa del Sol at the Last Minute

*UPDATED – Missing photos added

Can you book a place for an extended stay on the Costa del Sol in Spain at the last minute. Of course you can!

When we arrived at our apartment in Marbella, Spain on our very first winter getaway to the Costa del Sol in 2017 I said to the Love-goddess after doing some checking online, “I’m sure we could’ve flown over here and booked an apartment for two months after we got here.” And that has kind of stuck with me. We’ve never done it, but if we absolutely had to, I would have no problem doing exactly that.

This year finding a place to stay was a very different experience. For multiple reasons, which I won’t elaborate on, it was decided that we would book early. Normally, I don’t even think about checking for apartments until we are well into November. My working theory is that at that point, the property owners who have unrented apartments for the winter months are going into panic mode because they’re facing having their units sit empty all winter long without even having their monthly utility and mortgage expenses being covered.

Anyway, booking early this year led to a bit of a schemozzle. My first attempt at booking had me negotiating with a person over a lovely waterfront two-bedroom apartment. The individual would not come down to the price I wanted to pay so I went looking elsewhere. This resulted in me booking another waterfront two-bedroom apartment for less than I wanted to pay. Lucky me!

My luck only lasted two days and the owner abruptly cancelled our reservation. They can do that, but if they do, they cannot relist it for that same timeframe.… and they didn’t, I have checked. My thinking is that he or she got an offer from a previous renter for either a longer period or for more money and probably got paid in cash. They didn’t need us anymore.

So, back I went, hat-in-hand to the original apartment owner and said I was ready to book. Unfortunately, someone had booked a three-week period in the middle of the two months block that we were looking for. The net result was we booked the original place for a week at the beginning of our stay and for five weeks at the end of our stay. The title image above is the unit we booked for most of our stay this year. After that, I went searching for another apartment to fill in the three-week block.

That has all worked out and as I write this, we are in the second apartment. It is in a lovely area in the Old Town, a block away from the waterfront. Moving from one apartment to another was not as much hassle as I thought it would be, other than the taxi driver got horrendously lost because he was under the impression he was taking us to the town of Marbella. Fortunately, when the mistake was noted, he turned off the meter. So, no harm, no foul.

 

You Can Cancel and Rebook

One of the more positive aspects of renting through Airbnb is that you can cancel relatively close to the actual booking date and in most instances get all your money back. Frequently listings will state “free cancellation” or indicate a date by which you can get all of your money back if you cancel. So, it is possible to book a place quickly and then keep looking for someplace better. Given that we booked earlier than normal… all of this happened several months ago… in December, I began to think “why not keep looking for a single more suitable property and cancel the two I have booked”?

Knowing this, I did circle back and did another search in December, and I was definitely not surprised to discover that there were new choices available. In fact, I did it several times before we left home. And this is what this article is all about… me offering proofoffering proof to you that new listings will typically pop up, so don’t get your shirt in a knot if you can’t find anything suitable immediately, or if you lose out on something you like. Don’t give up. New listings will appear!

 

Why Do New Listings Appear?

This, of course, begs the question, why do new listings pop up? I don’t know exactly why, but off the top of my head I can think of several possibilities.

I will be using carousels in this article, but they look and act a little different than those in previous offerings. But the process remains the same. Click on the left image and they will pop in a larger, easier to view and read format.

People Cancel – As I said, with rental sites like Airbnb typically you have the right to cancel easily at no or little expense to you. It’s easy to imagine scenarios where someone has rented one place, and then they find something much cheaper or better suited to their needs a couple of months later in a different location and make the big switch. And then that first property reappears as being available in searches.

Property Turnovers – The whole Costa del Sol is an enormous tourist area for all of Europe… Especially in the summer months. That means there are lots of properties that are being primarily used as a vacation property much like we would use cottages at home.  Some of these vacation homes that in the past were  being used exclusively by the owners get sold, and the buyers turn them into short term rentals.

By way of example, we were speaking with a couple from Sweden in 2023, who had bought a property because the English owners, who were living there permanently, had to sell out and move back to England after Brexit to ensure that they received healthcare coverage. The new owners’ plan was to have an agency rent out their newly purchased holiday property when they were not using it themselves. There are all kinds of agents in the area who attend to rental properties owned by individuals in other parts of Europe.

Investor Conversions – Investors will be buying older properties and converting them into short-term rental properties and putting them on the market. The building we are currently renting in was one such property. The apartment we are staying in at the moment is obviously brand new and it is clear that a major renovation has recently been undertaken on the whole property.

I know this because when I searched the address in Google Maps the old building comes up, and it looks fundamentally different from the building we are in now. A real estate firm has converted an old single residence into some very nice apartments. They even added a story on top of the building.

New Building Projects and Infill – Again, this is essentially a tourist area, the economy is largely based on tourism, and there is lots of land. The net result is that there are all kinds of new properties being built that are being purchased either by individuals who want to use them themselves, or by individuals or firms who want to rent them out as short-term vacation properties

Like in many other places around the world, there are all kinds of new “infill projects” going on. This involves the tearing down of a small, older building and a  much larger building being built in its place. I can say this with great authority because at this very moment, there are several projects here in the Estepona Old Town that fit that description. The one in the photo below is just one of several projects we have seen just strolling around our general neighborhood.

Full Time Residents Decide to List Their Home  – I can also envision that some folks who have owned properties here for an extended period of time decide that they want to travel or move somewhere else for a short period of time; they want to get some of their ownership costs covered and decide to rent it out for part of the year.

To Tie This All Together –  Here is an image I took of one of the local English newspapers in 2023 that reported that the number of “rental beds” on the Costa del Sol had topped 500,000 in number. Keep in mind that all that accommodation stock is primarily in place to handle an enormous summer influx of tourists. That is why this is such a great place for Canadians to come in the winter. It is the off-season and there are way more properties available at that time of year than there are potential renters.

 

Is Renting Through Airbnb or VRBO the Only Way to Book?

No, there are other rental sites situated in Europe that typically will not pop up when we search in Canada. And there are sites at which you wouldn’t think about looking for short or semi long-term apartment rentals. We have used Spain-Holiday.com successfully to find a long-term unit, and I actually discovered a suitable property in Toledo for a weekend stay, Spain by accident on Booking.com fairly recently.

When you get to the Costa del Sol, you will discover that they are all kinds of real estate companies and short-term rental companies in the area from whom you can also rent. And of course, going through them means no big Airbnb fees for handling the booking or charges for cleaning. But you need to get here and search them out during your first stay. 🙂

We resorted to Airbnb this year because we have only ever spent one night in Estepona and really don’t have any contacts. We had no knowledge of any of the rental agencies locally. If we decide to come back here next year, we will be making a list before we leave town for sure.

 

Multiple Bookings

I mentioned that we had to make multiple bookings this year, but that certainly is not our preferred practice. We like to find one good unit and stay in it for the whole two months, which usually is fairly easy to do. Ultimately, we were fine with doing it this year because we were interested in comparing what it was like living facing the beach versus a charming apartment in the old town. Perhaps I will report back to you at the end of our stay how it all worked out. 🙂

That said, when you do search with some specific criteria, occasionally what will pop up are suggestions to book two different properties say for a month each. If you can live with that, the only thing you have to worry about is getting your stuff from one apartment to the other. So, it’s doable.

 

The Proof!

And now, the moment you have all been waiting for… the proof of how easily you can actually circle back for and find alternative apartments. Even after you’ve already booked or have delayed your search to a much later date than you thought you probably should have started.

I will provide two photos with each example. The first basically is a screenshot of the full search showing the top six offerings that popped up. The ones I decided to look at are indicated with a “red star”. The second photo is the property information page for my selection. You can see how much was being asked for monthly rent in the first image in these collections. For many of these, you will see that the price has been slashed because we were looking for an extended stay. I’m sure renters are thrilled when they can fill their apartment over the winter months in one fell swoop. 🙂

Search Criteria

My basic Airbnb search criteria were as follows. The apartment needed to have at least two bedrooms and two bathrooms… we do get company. There needed to be an outside sitting area.  It needed to sit directly on the waterfront or it had to have a great view of the Mediterranean. And it had to be available for the months of February and March.

My secondary criteria, that I could not build into the Airbnb search, were that ultimately any apartment we would rent needed to be within easy walking distance of amenities like grocery stores, restaurants, and public transit. I always check for those before I ultimately book.

I was looking for a single apartment that we could book allowing me to abandon the two-apartment approach we already had set up. However, I was also looking for apartments that might be of interest to other folks with different needs than  our own. I was already thinking about writing this piece. That is why I will show you two different listings for each search conducted. One for us and one for you.:-)

The December Search

I resumed my hunt in the middle of December. Here are the results.

December 19, 2024 – The first listing that caught my attention

This listing interested me because it was obviously in the front line overlooking Estepona’s port. Nice view of the water, just above the paseo.

December 19, 2024 – Second listing that caught my attention.

The second one was of interest because it was in a brand-new condominium project. It is quite a way from the waterfront, but I thought there may be those of you who are more interested in a clean, modern living space than where it is located in town.

The New Year Search

We didn’t pull the trigger on the apartment that I found in my December search, so I went looking again early in the new year.

January 5, 2025 – Listing number one

This one really caught my eye. I think if the balcony had been right on the front of the building overlooking the Mediterranean, I would have pounced on it.

January 5, 2025 – Listing number two

The second one was absolutely lovely. Right on the waterfront, in a park like setting. However, it was well outside of town and if you were to stay there, you would have to rent a car for the whole two months. For those of you who must have a car if you’re going to be away from home two months, this would’ve been a great option for you.

The Week Before We Left Home Search

I looked again the week before we were set to leave. So, I wasn’t really looking to make the switch at this point, but I did want to see what was available. I was not disappointed.

January 22, 2025 – Listing number one

A penthouse overlooking the port for reasonable money. If we had decided to go to Estepona at the very last moment, I’m sure I would have booked this one. It only has one bathroom but when you’re looking to take possession in a week, beggars can’t be choosers. 🙂

January 22, 2025 – Listing number two

If I was going to be booking just a week before we were set to go to Spain, I decided I would probably need to expand the search and look in other towns we had already stayed in before. So, my second search was in the town of Nerja and I was amazed to find an apartment in the Fuentes de Nerja complex where we have  stayed two times before, was available.

Searching After We Got to the Costa

At the end of our first week when we were about to switch apartments, I thought what the heck why don’t I check to see if there is a single apartment available for the rest of our stay? It did not come as a surprise to me that there were units that would have worked for us.

February 7, 2025 – Listing number one

Two bedrooms, check. 1 ½ bathrooms… Good enough I guess… check. View of the Mediterranean, check.

February 7, 2025 – Listing number two

The building is on the beach, but there is clearly no good view of the water. And it doesn’t look like there’s an outdoor place to sit. So, it doesn’t check all the boxes but hey, any port in a storm I suppose if you need to be in an apartment the following day. 🙂

 

Never Give up Searching!

I really enjoyed writing this article because it reminded me that you really could come to the Costa del Sol and find a reasonable apartment somewhere interesting at the last minute – even if you weren’t able to find something previously. The Costa del Sol is 200 km long and there are lots of interesting cities and towns to stay in. And an apartment that pretty closely suits your needs would likely be available.

So, if you’ve just came in from shovelling the driveway… yet again… and you are thinking that maybe you should leave for Sunny Spain as soon as you can book a flight – perhaps today is the day to start searching for an apartment!

Stay warm everybody.