For many years, the default choice for an international visitor to Sydney was one of the city’s five-star hotels. Comfortable, concierge, valet and room service – but open to preying eyes of the public. And, ultimately, one hotel room looks like the next.
The post Covid influx of touring artists, as well as high net worth families and business leaders, are looking for something different: a private residence they can temporarily call home.
Penelope Cobbold, founder of Sydney luxury property company Cobbold and Co., specialises in luxury property rentals in Sydney, sourcing and managing exceptional private homes for international visitors, prominent families, musicians and VVIP guests. Much of her work happens quietly; some of the houses she arranges never appear publicly online at all. Discretion and privacy are key drivers of her business.
We spoke to Penelope about why private homes are becoming so sought after, what high profile visitors look for when they come to Sydney, and Penelope reveals that the most expensive house is not necessarily the best one.
Why are more visitors choosing a private home rather than a hotel?
Families are probably the easiest example. It doesn’t matter how luxurious a hotel is – you are still living in hotel rooms.
If you have children, perhaps a nanny, grandparents coming and going, security or other staff, a house makes life enormously easier. You have a kitchen, a sitting room, outdoor space, perhaps a pool. Children can have breakfast in their pyjamas. Everyone has somewhere to go without having to meet in a hotel lobby.
For longer stays particularly, people want to settle into a lifestyle rather than feel as though they’re living out of a suitcase.
Is privacy part of the appeal?
Very much so. For some clients privacy simply means having their own front door and not walking through a hotel lobby several times a day.
For somebody extremely well known, it becomes more complicated. You have to think about how visible the house is from the street, whether cars can enter privately, the position of neighbouring properties, gates, garages and whether photographers could realistically wait outside.
A spectacular house is not automatically a suitable house for a high profile guest.
What sort of requests or riders do VVIP guests have?
Everyone is different. What feels luxurious to one person can be completely unimportant to someone else.
I can think of one client who absolutely had to have a waterfront and a jetty. Another wanted an ice bath and to be able to walk to a beach. Someone travelling with young children might prioritise a lawn, a pool and separate bedrooms over an extraordinary view.
Touring artists often have quite specific requirements because there may be management, security or other members of the touring party to accommodate. It varies from those who want to stay in their home, so a home gym and perhaps private chef are requested. And then there are those who want to get out and mix with the locals, a beautiful home that’s an easy walk to the beach or the cool cafés and bars.
My job is really to understand how somebody wants to live while they are in Sydney before I start showing them houses.
So the most expensive property isn’t necessarily the best?
Absolutely not. A $50 million house can be entirely wrong for someone who desires a much more relaxed family setting. I’d never count it out, but having informed options is the key. No one likes to have their time wasted!
People sometimes assume every international VIP wants enormous marble rooms and extraordinary formality. They often want exactly the opposite. More likely they’ll want something spacious, private and comfortable where they can close the door and feel at ease.
You are known for finding houses that aren’t publicly advertised. How does that work?
I’ve been doing this for a long time and Sydney is quite a small world. Sometimes I know an owner who might consider renting if the right person came along. Sometimes somebody knows somebody else. One conversation leads to another. I suppose, in a sense, it’s a match-making mission. Matching the right client with the perfect residence.
I am frequently asked for something that isn’t sitting on a booking platform waiting to be found. Everyone wants that X Factor. Something special, and different from everything else.
That is where local relationships matter. You can search online for a five-bedroom waterfront house with a pool. You can’t necessarily search for the owner who has never rented their house before but might quietly consider doing so for the right family.
(It has led to Cobbold becoming known among clients for what some describe as her Sydney ‘little black book’.)
Who are the people looking for these houses?
A very broad mix, usually interesting, successful and hardworking people.
We look after international families coming to Sydney for several weeks or several months, senior executives relocating here and looking for executive rentals, people visiting family and, increasingly, people connected with the film and music industries.
I’ve been asked to source houses for internationally known musicians, touring pop artists, actors, billionaires and occasionally people whose public profile probably makes privacy even more desirable.
They don’t all want the same thing. The common denominator is usually that they want discretion and they don’t want a conventional hotel experience.
Do owners ever worry about renting their houses to famous rock stars? Do they imagine wild parties?
Sometimes they do, but the reality is usually much less dramatic.
Most famous rock stars are wild on stage and then want to go home, put their feet up and watch television like everyone else. One of the first things we’re often asked is whether American sports can be properly connected to a smart TV.
We once had a very famous guest who was so tidy he actually made the beds before he left! It happened to be Halloween and, as a joke, he had hidden little plastic spiders all around the house.
The owner and I kept discovering them and screaming before we realised what he’d done. It was very funny and rather charming, and he apparently was a wild one in his day.
The truth is that most high profile guests are incredibly respectful of the houses they stay in. They are looking for privacy and normality, not somewhere to behave badly.
Is Sydney particularly good for that?
I think it is. Sydney has extraordinary houses, particularly around the harbour and beaches, but it also has a wonderfully relaxed attitude towards famous people.
Most Sydneysiders really aren’t that interested. Half the time they probably don’t even know who they are.
I live in Tamarama and we’ve had extremely famous people wandering around the beach and cafés with remarkably little reaction. A very famous redheaded actress was around here for several days and most people simply had no idea.
That anonymity is quite relaxing when your normal life involves being recognised everywhere you go.
Are there parts of Sydney that international clients particularly want?
The eastern suburbs and harbour are always in demand, so Point Piper, Vaucluse, Bellevue Hill, Darling Point and the beaches around Bondi and Tamarama.
Palm Beach offers something completely different and can be wonderful for somebody who wants to disappear. On the north side, Mosman and Balmoral are particularly good for families because you can have beautiful houses, harbour access, fantastic hiking and a slightly quieter way of living. But, again, I try not to start with the suburb. I start with the person.
Your background is rather different from the traditional property world
I’m British and very horsey. I actually started life in Australia as a backpacking polo groom, and once taught a rather famous businessman how to get out of the saddle properly to whack the ball. Horses and polo were a big part of my life and probably still influence the way I deal with people.
You meet people from every imaginable background around horses, including some extremely successful and prominent people, but nobody particularly cares who you are when there is a horse to deal with.
Perhaps that gave me an ease around people and a lack of interest in celebrity that is useful in this business.
What does discretion actually mean in practice?
Not talking. Owners need to trust us with their houses and guests need to trust us with their lives.
We may know who is arriving, who is staying with them, what security arrangements are being made and where somebody will be for several weeks. That information is nobody else’s business.
Has the definition of luxury changed?
I think it has. The traditional idea was service: somebody carrying your bag, room service at midnight, marble bathrooms.
Those things are still lovely. But sometimes room service at midnight is being able to raid your own well stocked fridge in the nude without having to speak to anybody.
For many sophisticated travellers now, luxury is freedom. It is waking up and making coffee in your own kitchen. Swimming in your own pool. Having friends over for lunch. Lolling around and letting the children run outside. Walking down to the harbour without make up and having to pass through reception. And, occasionally, being able to spend three weeks in Sydney without anybody knowing where you are.
A considered choice in Sydney
For Penelope Cobbold, that is ultimately what the private house experience offers: not simply more space, but the ability to live in Sydney on your own terms.
Through Cobbold and Co., she sources and manages luxury private homes and VVIP accommodation across Sydney, including Point Piper, Vaucluse, Bellevue Hill, Darling Point, Tamarama, Bondi, Palm Beach, Mosman and Balmoral, for short term and medium term rentals, extended family visits, executive rentals and relocations, and international music and film clients.
Cobbold & Co. also provides luxury property management for owners of high end homes across Sydney’s eastern suburbs, harbour and beaches.
Sometimes the right house is publicly available. Quite often, finding it still comes down to knowing who to call.
All imagery credit: Cobbold and Co.
