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An Owners Journey

Writer's picture: Steve OsborneSteve Osborne

Why Do We Own Holiday Lets?

Honestly, I’m not entirely sure how we’ve ended up here. Owners of two stunning holiday lets? It sounds far grander and more intentional than it really is. I’d love to tell you it was all part of a clever financial master plan, a savvy strategy to secure our financial independence while sneakily giving us an excuse to enjoy our investments. But if I said that, I’d only be telling you a sliver of the truth.

So, how did this happen? Let me take you on a ramble through my thoughts and see if we can unravel how we ended up here.


It All Started with a Love Affair

Not the scandalous kind – calm down. This was a lifelong love affair with a place: Swanage. My first visit was as a pale, ginger nine-year-old back in 1977. I fell in love with the sea, the crabbing, the ice creams, and even the makeshift putting green I fashioned on our camping pitch at Burnbake. Swanage became our yearly pilgrimage, often more than once a year, a sanctuary for my family and me. It felt like a second home, a place where we could escape, unwind, and just be.

Swanage became so deeply entwined in our family’s story that when my dad passed away when I was 16, we scattered his ashes on the downs at Peveril Point. And years later, when I proposed to my wife, it was at that very same spot. Romantic, eh?

Proposal on Pervril Point
Proposal on Pervril Point

Fast-forward a bit, and it felt only natural to pass on this love of Swanage to my own children. We started taking them down once or twice a year, indoctrinating them with the magic of the place. I’m pleased to say it worked, they’ve now infected their own families with the Swanage bug and bring our grandchildren down regularly, keeping the tradition alive.


From Caravan Dreams to Brick-and-Mortar Reality

Back in 2016, we thought: “Why keep forking out for accommodation when we could have a place of our own?” The obvious first thought was a caravan. But after a bit of deliberation (and some wisdom from my son, who was studying Economics at uni at the time), we realised caravans weren’t for us. For one, they’re a depreciating asset – which is posh-talk for “a bit of a money pit.” But more importantly, caravan parks shut from November to March. And that’s our favourite time to visit. Fewer crowds, quieter streets, and a slower pace – that’s when Swanage feels like its true self.

So, we turned our attention to bricks and mortar. Enter Rightmove – the internet rabbit hole of house hunting. One day, while scrolling after looking at caravans, we stumbled upon a flat for sale in a gorgeous Georgian building off Seymer Road.

Of course, we had to go for a nosey. But here’s where things got very un-British. While gawping at the building from the outside, a man stepped out of the front door. Now, I’d have awkwardly shuffled away, staring at my shoes, but Jackie is made of bolder stuff. Without missing a beat, she asked the poor bloke if he was the owner of the flat for sale.

Turns out he was. And before I could die of embarrassment, Jackie had charmed us an impromptu viewing.

The flat itself was a bit tired, years of holiday letting had left it looking worn around the edges. But the location was perfect: views of Old Harry Rocks, courtyards front and back, and just a few steps to the downs overlooking Swanage. Plus, you could see the very spot where I proposed to Jackie and where my dad’s ashes rest. It felt like fate. We made an offer, it was accepted, and just like that, 1 Belvedere Lodge became our little haven in Swanage.


A Holiday Let, Not a Second Home

From the start, we were clear: this wasn’t just for us. It would be a luxury holiday let, shared with other people who love Swanage as much as we do. Now, I need to hop on my soapbox for a second: holiday lets and second homes are not the same thing.

Second homes sit empty for most of the year, don’t contribute much to the local economy, and until recently, dodged council tax. Holiday lets, on the other hand, are part of the hospitality industry. They bring tourists (and their spending) to the area, create jobs, and pay business rates. So, if you ever hear holiday let owners being lumped in with second-home owners – feel free to have a little righteous indignation on our behalf.

Right, rant over. Back to the story.


And Then There Were Two

Belvedere Lodge in Swanage, Dorset and Porth Sands in Porth, Newquay, Cornwall
Belvedere Lodge in Swanage, Dorset and Porth Sands in Porth, Newquay, Cornwall

After setting up Belvedere Lodge, a friend of ours – who happens to be our mortgage advisor – asked if we’d considered branching out. He lived in Porth, Newquay, and reckoned it would be the perfect place for another holiday let.

We were intrigued. So, we took the five-hour drive down to Cornwall to have a look. Our top prospect was a beachside property, but the estate agent made a right mess of things – there were guests staying, and we could only view it from the outside.

Disappointed but undeterred, we decided to grab lunch at Gwenna Teahouse  (we highly recommend, by the way). While we were chatting to the owner, she mentioned a penthouse flat in the purpose built holiday let next door that had just fallen through on its sale. Her husband had the keys, and before we knew it, we were standing in the living room, looking out at the waves rolling along the cliffs of Porth Island.

It was love at first sight – again, Porth Sands became ours. Serendipity had struck twice, and now we’re the proud owners of two beautiful holiday lets.


Sharing the Joy

Running these holiday lets has been an unexpected joy. There’s something deeply satisfying about sharing these special places with other people – knowing they’re making memories and falling in love with these locations just like we did.

So, that’s how we got here. Not a grand plan, but a series of serendipitous moments, a bit of boldness from Jackie, and a lot of love for two magical places.


30years after the proposal, we still sit in the same spot with very grateful hearts!
30years after the proposal, we still sit in the same spot with very grateful hearts!

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