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You ask, we do. It’s as simple as that. Here at Wild Oyster, we pride ourselves on a ‘can do’ attitude, whether you’re a holiday guest or a holiday home owner. 

Originating from Weymouth in Dorset, home of the Sailing Olympics 2012 and the famous Jurassic Coastline, we are a new and independent agency offering the best holiday lettings services.

We have around 30 successful years experience in the letting industry, and combined with our local knowledge, we can be part of making your holiday one you will remember. The way we do that is offering the best services that you choose. 

Away for a special occasion? A birthday maybe? Imagine arriving at your holiday home to a birthday cake that you’ve pre-arranged with us, or even to some bottles of wine in the fridge, along with some shopping. We can have it all waiting for you. And, we can even arrange trips for you if you want us to. We offer this additional concierge service that suits you and your preferences. You can relax and settle knowing that everything else is taken care of. 

“On booking, our concierge service allows guests to request items to be delivered to their chosen holiday home for their arrival. We can also book trips, theatre seats and restaurants, in fact –  if they want a birthday cake, we can even arrange that! We will do our utmost to get what our guests want.”

All of our homes have been personally visited to ensure that they are suitable for your holiday. From the beds to the kitchen cutlery, we have checked it all so that it is up to the highest standard. Everything is taken care of so that you can indulge and make your holiday extra special.

We are passionate about providing the best services to suit your holiday expectations. Whether that’s a large group, or pet friendly homes, we have something to suit you. Our aim is to ensure that you go home relaxed, happy, and relieved that you booked with Wild Oyster. We want to be your holiday friend that’s made your holiday harmonious. 


If you’re thinking of letting out your property to holiday guests, then let us help you. We can assist in making the process as simple as possible by doing all organisation, planning, and taking care of all the work associated with managing the property. 

Here at Wild Oyster, the team has an aim to provide reduced transparent fees for owners, whilst maintaining a high level service, which will reduce the level of input by the owner. It’s important to us that we dedicate a fantastic service which still is affordable. 

We recognise that, as an owner, the commission fees are extremely important and they have an impact on your property investment. Being owners of holiday lets ourselves, we understand you do not want to be crippled by fees. So, we have calculated an extremely competitive package, starting from 13% in the first year.

Alongside competitive commission rates, we also offer an eco-friendly cleaning service.  The Green Earth Cleaning Company is a subsidiary company alongside Wild Oyster, which can be organised by us in line with the check in dates of holiday guests. 

We are seeking further holiday cottages to keep up with demands. We use a multitude of reputable advertising sites to provide maximum online exposure, and we will manage all your bookings and contact with guests. If you want to know more, or discuss our competitive commission rates, then please contact us.


Founded by Victoria Bailey and Jason Hall, Wild Oyster has a team of well experienced directors, who both have a wealth of knowledge in holiday lettings. Being local to the area, both Victoria and Jason also know about the tourism in Dorset and the leisure industry, so are happy to help with any questions about the area of your stay. It’s the perfect combination of expertise for organising the perfect holiday!

Meet the Directors

Victoria Bailey

Travelling the world and experiencing accommodation that’s one extreme to the next, Victoria has seen what makes the best holiday stay. She’s spent many years either backpacking around hostels, or relaxing in luxury villas. Every experience has taught her what’s good for a holiday stay, and what can be improved in each circumstance. Having first hand experience of the best of accommodation has meant that she knows how to create the perfect holiday stay.

“The longest I travelled was 18 months, and during this time I could honestly say a small number of hostels offered substantially better accommodation than a hotel room.” 

From her adventurous experiences and love to travel, Victoria realised what counts in the best accommodation. That being: having everything that you, personally, want for your holiday.  The key is being catered for what you want the most; having everything you need, the accommodation being clean, and having a good comfortable bed (of course!).

Not only does Victoria have extensive travel experience, but she has a vast amount of professional experience, too. She has worked in many different industries that has shaped her into being a trustworthy, organised and brilliant Director of Wild Oyster. Victoria worked in a Commercial Estate Agents for  2 years,  and then moved into the banking industry for 16 years. Following this, she was a serving Police Officer in Dorset Police, before retiring after 16 years service at the rank of Sergeant. And, she also has her own properties that she successfully lets out currently.

“I believe in offering a first class service which is affordable. Homeowners may feel tied to their holiday let, and we want to relieve their stress. Having a financial background really helps with managing figures, and I am confident that we can provide a profitable income for the owners, as well as keeping the home in great order.” 

Jason Hall

From restaurants to managing accommodations, Jason is a proven successful business man. He currently has two established eateries in Weymouth, rating in the top 5 of Tripadvisor. And, he also runs his own profitable holiday let, which provoked him to consider his experience in France Ski Resorts; here, he managed luxury accommodation that provided catered facilities and concierge benefits.

Having experience in Jason is passionate about providing the best accommodation for guests and to ensure they have everything they need for their holiday. 

“I get a great sense of satisfaction knowing that guests have had the best time in our holiday homes. I think having a ‘can do’ attitude is very important; we can go above and beyond if it means that a family – who has waited a year to go on their holiday – can go home and feel that they’ve really had the best time. That’s what it’s all about.”


Just like we have a passion for helping people with holiday homes, we also have a passion for helping charitable causes. It’s something that it is at the core of our wild Oyster values. 

We want to give back to those who need it, and have offered our services to people affected by different circumstances, in order to give them opportunities to make memories on holiday.

Lexi May Trust

We have offered 4 weeks of free stays to families with terminally ill children, giving two weeks in two different holiday homes. It breaks our heart that there are families and situations such as the Lexi May Trust supports, and we want to do everything that we can to help. We provide free stays in the hope that children and families can make memories to remember. 

The Lexi May Trust supports children with terminal illnesses or life limiting conditions in Dorset.

Team Endeavour

Their mission is to make a difference, and we want to help them do that. Team Endeavour is a charity that raises money and awareness for children and families of the Armed Forces who are suffering through illness, hardship and poverty.