From Royal Marine to 96 holiday lets: Jamie Miles on running Anglesey Holiday Lettings
- Apr 18
- 8 min read
Jamie Miles spent 26 years in the Royal Marines and five years as a military advisor on Game of Thrones before "accidentally" becoming one of the Isle of Anglesey's most prominent holiday letting operators.
Today, his company, Anglesey Holiday Lettings, manages 96 properties under a fully in-house, turnkey model. In this Host Planet Playbook feature – powered by property management software, Hospitable – Jamie shares what he's learned about scaling in a rural market, why dynamic pricing cost him money, how he navigates Welsh regulation, and the three pieces of tech he couldn't run the business without.
Meet Jamie Miles
Jamie Miles is the director of Anglesey Holiday Lettings, an in-house, full-management short-term rental company operating exclusively on the Isle of Anglesey – the island off the north-west coast of Wales. The business currently manages 96 properties "and growing," and is built on a deliberate, local, non-call-centre model.
His route into the industry wasn't conventional. A Cornishman by birth, Jamie spent 26 years in the Royal Marines, serving multiple tours in Iraq, Afghanistan, and elsewhere. He discovered Anglesey through a Royal Navy friend during a long weekend visit – and began using it as a pre- and post-deployment stop-off because, in his words, "it's an absolutely beautiful part of the world." When retirement from the Marines came into view, he moved to the island permanently.
Jamie also spent five years as a military advisor on HBO's Game of Thrones, running discipline, scene coordination, and extras training on productions including The Battle of the Bastards. As Game of Thrones wound down, what he'd assumed would be a part-time income from a single holiday cottage grew – almost by accident – into a 96-property operation.
"I moved to Anglesey in 2014, having spent seven years very slowly building a property with an attached holiday let. A good friend said, 'Do you want to look after mine?' And here we are. We're managing what we are purely by accident."
What makes Anglesey Holiday Lettings different
In a market increasingly dominated by large, centralised operators, Jamie's core positioning is deliberate and un-flashy: not a call centre.
"All of my staff are in-house. They're all on hand because they're local. My team and I know the properties inside and out, we know the owners – I've been to weddings, funerals, and everything in between with owners. We're a friendly, purposely small outfit."
Every function sits under one roof: housekeeping, compliance, maintenance, a professional in-house laundry unit, and arrival essentials like welcome packs. For owners, this delivers what Jamie calls a "turnkey event" – nothing is subcontracted, everything is accountable to one team.
The limit is built into the model. Jamie has capped the portfolio size intentionally:
"There's a limit of how many you can handle before you start diluting yourself."
The skills that transferred from the Royal Marines
Asked what carries over from 26 years in uniform to running a rural holiday lettings business, Jamie is direct: "Attention to detail – and walking a very tight rope in a very strong wind while spinning 18 plates. That's the military world. That's also the holiday lettings industry."
The second through-line is communication, "being able to communicate at the highest level and the lowest level." In a business that juggles guests, owners, cleaners, tradespeople, OTAs, and regulators on any given day, the ability to switch register between a distressed guest on a Saturday night and a corporate OTA account manager on Monday morning is a genuine, underrated edge.
How to keep owners happy (and why you can't)
One of the most quoted lines from the interview is Jamie's reframe of owner relations: "You can never keep all owners happy. I've learned to manage their expectations very well. I build up trust with them, and then they leave me to it. I don't aim to make my owners 100% happy. I aim to deliver an honest product to the guests, keep the guests happy, make sure the product delivers – and expect that you can't keep everyone happy."
The philosophy is quietly radical for a service business: prioritise guest experience and product honesty, and use trust – not reassurance – as the mechanism for keeping owners onside.
Operating in Wales: "a 17-point pincer movement"
No UK property manager conversation in 2026 is complete without talking about Welsh short-term rental regulation, and Jamie is blunt about the operating environment: "It is twice as hard to make money in this business than it was 12 months ago – or in fact two years ago."
He lists the pressures: EPC and net-zero requirements, business rates, Article 4 directions, licensing proposals, and a broader policy environment he characterises as a "17-point pincer movement" on the industry. The issue, in his view, isn't any single regulation but the cumulative, compounding weight of them – and a policy apparatus that doesn't appear to be modelling the combined effect.
His message to Welsh lawmakers: "Get your data right. The numbers they quote – visitor numbers, spend, GDP contribution, tourism impact – if they got that right, they'd probably leave us well alone. On Anglesey we have two industries: tourism and agriculture. Both are under massive attack from all directions."
The most expensive lesson: dynamic pricing in rural markets
The most striking operational insight in the conversation is Jamie's direct challenge to received wisdom on dynamic pricing: "Don't shoot the messenger. Based on data, dynamic pricing does not work in rural environments like ours. There isn't enough data. We stepped away from it. That was the most expensive lesson learned – leaving an algorithm to do things. We left an awful lot of money on the table."
This isn't a rejection of data-driven pricing. It's a rejection of off-the-shelf algorithmic pricing in markets where the comparable data the algorithms depend on simply isn't dense enough to produce reliable signals. Anglesey Holiday Lettings replaced the algorithm with a specialist: "I have a very intelligent man with eight screens on his desk. He uploads 58,400 prices daily, in his own tool. We've gone back to the trusted man – boots on the ground, sat there, looking at the data and doing these things to great success. I won't tell you his name because I'm not going to share him."
The lesson for other rural and semi-rural operators: treat dynamic pricing tools as inputs, not decision-makers. In thin-data markets, human judgement layered over the data still beats the algorithm.
Why single-arm businesses are fragile: the Covid lesson
The second strategic lesson is one many STR operators learned the hard way in 2020, but Jamie states it plainly: "Being solely reliant on holiday lets – Covid was a massive lesson. We've diversified slightly, and we're looking to diversify our supply further. If one arm of the business struggles because of something like that, we need to be better prepared."
For operators who've grown comfortably since 2022, it's a timely reminder. Concentration risk doesn't announce itself.
The tech stack running 96 properties
Jamie's quick-fire answers on tools are illuminating:
PMS: SuperControl
Essential tech: Touch Stay
Dynamic pricing: None – Jamie uses a human specialist
Communication preference: Telephone over AI response
Pets: Absolutely yes
Hot tubs: Reluctant yes
Self check-in or personal welcome: Self check-in (backed by data)
Jamie said: "I surveyed 25 properties' guests. 67% found a personal welcome intrusive. So we're 100% self-check-in, with us on hand. Trying to get round 96 properties in an evening – it's a lot of staff. Have they arrived yet, have they arrived yet."
The self check-in finding is the kind of uncomfortable operator data that rarely makes it into public debate – most hosts assume a personal welcome is a premium touch. Jamie's actual guest research suggests the opposite for the majority of visitors.
Most memorable guest moment
Jamie has hosted "some really famous people and some really awful people." The moment he volunteered: "We hosted I'm a Celebrity, Get Me Out of Here guests when they were filming on the North Wales coast during massive storms. One of them drank the entire honesty bar – about ten bottles of champagne – and didn't replace them."
The ultimate goal
Asked about his endgame, Jamie's answer reads like a manifesto for the next wave of intentionally-sized property management companies: "We've set a limit on the amount of properties we want to take on, because part of our business is delivering on a promise. When you're operating a full in-house turnkey event for a property owner and being on hand for those guests, there's a limit before you start diluting yourself. My ultimate goal is 75% of the portfolio crossed the line, all my owners smiling, five stars on Google reviews, a happy team. Happy guests, happy owners, good revenue, happy team. We're aiming to continually improve."
It's a counter-model to the venture-backed scale story that's dominated the STR management narrative for half a decade: deliberately capped, locally owned, quality-controlled, and built to outlast a regulatory cycle.
Frequently asked questions
Who is Jamie Miles? Jamie Miles is the director of Anglesey Holiday Lettings, a short-term rental management company operating exclusively on the Isle of Anglesey in Wales. He is a 26-year Royal Marines veteran and was a military advisor on HBO's Game of Thrones for five years.
How many properties does Anglesey Holiday Lettings manage? The company currently manages 96 properties under a fully in-house, full-management model, with a deliberate cap on portfolio size to protect service quality.
What does Jamie Miles think about dynamic pricing? Based on his own operational data, Jamie believes off-the-shelf dynamic pricing tools do not work effectively in rural short-term rental markets because there isn't enough comparable-set data for the algorithms to price accurately. His company replaced algorithmic pricing with a specialist human revenue manager.
What is the biggest challenge of running short-term rentals in Wales? Jamie describes the current Welsh regulatory environment as a "17-point pincer movement" combining EPC and net-zero requirements, business rates, Article 4 directions and licensing – and says it is "twice as hard to make money" today compared with two years ago.
What tech stack does Anglesey Holiday Lettings use? The core stack is SuperControl as the property management system and TouchStay as the digital guidebook tool. For pricing, the business uses a dedicated in-house human specialist rather than an algorithmic tool. Jamie prefers phone calls over AI-generated responses for guest communication.
Does Anglesey Holiday Lettings accept pets? Yes. According to Jamie, pets help to generate a large percentage of the company's revenue because Anglesey is a dog-walking destination.
Does the company offer self check-in or personal welcomes? 100% self check-in with the team on hand. Jamie's own guest survey across 25 properties found that 67% of guests found personal welcomes intrusive.
The bottom line
Jamie Miles's story is a useful corrective to two prevailing narratives in the STR world. First, that scale is the only story worth telling – his capped, in-house model is built on the opposite premise. Second, that algorithmic tooling has settled the operational questions – his experience shows that in rural markets, human judgement still outperforms the algorithm.
For operators in rural or regulation-heavy markets, the Anglesey playbook is worth reading twice: stay local, diversify supply, cap the portfolio, invest in digital guidebooks, and be honest with owners about what you can and can't deliver.
This interview is part of the Host Planet Playbook series, sponsored by property management software, Hospitable. The series features 30 leading property managers from across the globe. Click here to download your free copy of the Host Planet Playbook. Interested in running your rentals on autopilot? Give Hospitable a try and get 25% off for the first three months.
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