Get in touch about letting your property

Holiday Letting on the Isle of Wight

We are a holiday cottage letting agency on the Isle of Wight who find exceptional homes that make great holidays. Our high standards are reflected not only in our portfolio, but the feedback left by happy guests that holiday with us year on year. They trust us as an agency to bring them the best.

• Your own dedicated Property Manager

Emma will hold your hand the whole way, supported by our team of local experts in our Island office, as well as in-house administration, marketing, financial and IT specialists back at company HQ.

• SEO and PPC campaigns tailored to letting your property

We rank for thousands of high volume terms as well as the long tail high conversion terms, and optimise the website for ease of use to let people find the right property as quickly as possible.

With a combination of paid marketing, social media, re-targeting and tailored email campaigns we can maximise your bookings and increase online visibility.  

• Live control of your account

Log in to your owner account to see live availability, questionnaires, all your finances and amend any details whenever you like. You'll know what you'll be paid and when thanks to our simple and transparent holiday letting agency fees.


The Island is littered with picturesque villages and small bustling towns, spectacular coastline, the famous Needles and over half the island is designated an Area of Outstanding Natural Beauty. There are some amazing places to visit with unique character and heritage, famous historic monuments include St Catherine’s Oratory and Tennyson's Monument.

Emma - Property Manager

Local experts on the Isle of Wight

Our Island Office is manned by a team of local experts who’ve been handpicking properties on the island for the past 12 years. Now part of Classic Cottages, a family company since 1977, we’re going from strength to strength with national visibility and faultless administration.

The UK holiday cottage sector has seen considerable growth over the last 10 years with the advent of ‘staycations’ and the challenges sometimes faced when traveling abroad. The island has been no stranger to this growth with easy access to London, world class sailing events, a laid back approach to life and the appeal of an ‘island escape’ without the need for a passport.


'‘We were really impressed by your efficiency, sincerity and obvious ease in engaging with your customers.  You inspire confidence in your company, so we're very happy to let our property through you.’ 

Owner of Primrose Cottage, St Helens (3645)


Holiday let management

Whether you’re on or off the island, you can rely on us to look after your property to the highest of standards. We’ve a range of Managed Services to suit your situation, from changeovers to maintenance, repairs to regulatory requirements. We are able to organise and administer all you would need to keep your investment running at the top of its game.

We use a professional photographer, included in the registration fee, where the Property Manager assists with the styling to show off the best assets of your property. Full descriptions are written about the property and lots of information added about the local area and amenities.


How much can I earn?

Island house prices run around 8 to 10% below their mainland equivalents which gets you off to a good start and research into the profitability of holiday cottages by county shows that the Isle of Wight has the second highest investment index. 

‘Hot properties’ are those with sea views, renowned for their appeal, however countryside locations also have their place in the market. The key to success, however, is quality. A rise in demand has lead to increased expectations but this in turn unlocks longer rental seasons. 

The style of property can affect the level of income, figures showing that two bedrooms and two bathrooms perform the best across the whole year, with larger properties doing well in the peak summer season as they can cater for more than one family at a time. The holiday season on the island starts at Easter and ends in October, however we are seeing an increase in popularity in short breaks out of these times.  

Purchasing an existing holiday home has the advantage of history of income, and often come with ‘room for improvement'. We can help you identify potential upgrades to increase revenue.

Each property is individual so we won't give you ballpark figures here. Instead it's best to speak to our island team, who all live and have worked on the island for many years so are able to give advice and local knowledge with no obligation. We have worked hard to develop close partnerships with local Estate Agencies to maximise our knowledge and understanding of current market trends. This is an area where the island excels itself, as we all live and work so closely for one common goal. 


What should I buy?

A property that you love! As above there are business-minded considerations but with those in mind, the key questions to ask when looking to buy a holiday home are:


> Does it have a ‘wow’ factor, for example garden or balcony with sea views? 

> Can you walk to local amenities and places to eat?

> Is there a private outdoor space with outdoor furniture for dining?

> Are the external and internals of the property well maintained and in good order?

> Is there enough living and dining space for the number of guests a property can accommodate?

> Can you offer flexible bedroom configuration, for example two doubles and one twin?

> Is there off street parking private to the property?


We can advise on renovations, fittings and furnishings, legislation and all things holiday letting to make sure your property is reaching its full potential but at the end of the day, it is your investment so the most important question you should ask yourself is:

> Would I go there myself on holiday?

Case study of holiday letting on the Isle of Wight

One of our latest additions to the portfolio is Mariners located on the Seaview Duver with a living room on the first floor to maximise the spectacular sea views from the balcony. We met with the owners over the Christmas period and they were keen to start marketing their property as soon as possible. From our initial visit it took two weeks to have Mariners live on our websites. Within days we were receiving bookings and within two months have achieved over 20 weeks booked. Needless to say the owners have been very pleased with the results. 

Why choose the Isle of Wight for holiday letting

A little landmass floating just off the south of England, the Isle of Wight is less than two hours’ drive from London but feels like a million miles away. A ferry ride across The Solent marks the start of your island adventure and for a truly unique travel experience, try the last remaining Hovercraft service in the world. Step back in time in the most positive of ways, for a distinctly slower pace of life where you still have WiFi.

We have our own foody scene; being surrounded by the sea has the obvious advantage of the freshest seafood and with many homegrown products, the varied and excellent eateries specialise in making the best of local delicacies. Most places to eat are made all the more special by their spectacular sea or countryside views and internationally renowned events such as Cowes Week add to the atmosphere.

Tourism generates over £550 million a year into our economy with a third of all employment being within this sector. The island has something for all ages, year-round making it a thriving holiday destination and lucrative investment for holiday home letting.

Specific villages and areas that have proved, over time, to be popular include Yarmouth, Seaview, Bembridge, Ryde, Cowes and Ventnor, all of which are located along the coast with many properties boasting sea views. However with the varied landscape of the island, the West offers a wealth of rural charm in villages such as Godshill, Brighstone, Newtown and Calbourne.

Friendly faces in the Island Office

Customer Support Administrators
Rachel C always has a smile on her face and with ten years in the office, knows every island property inside out to help guests find the best property for them.

Teressa P travelled the world before helping EFL students make the most of a visit to the island. And now she welcomes our guests.

Managed Services Administrator
Rachael F speaks fluent French and once ran her own holiday cottage business in St Barts so we snapped her up as soon as she stepped foot back on the island.

Office Manager
Chris T coordinates our sales and marketing in his wide array of colourful polo shirts.

Property Administrator
Jade H has a Geography Degree and qualifications in Tourism and Business as well as useful experience from the Hotel and Hospitality sector here on the Island. 

Property Manager
Emma C brings a wealth of experience in retail, travel and property sales and residential letting. She has great enthusiasm, a love of excellent property and an eye for detail which has been greatly appreciated by all our property owners.

Mark C loves the industry so much he is currently a board Director and Chairman of and sits on the Island's Tourism Marketing Panel.

Hints and tips for letting your holiday cottage

Carefree Breaks and the Classic Foundation

Carefree Breaks and the Classic Foundation

Providing respite for unpaid carers with time away to themselves in a holiday cottage.

Letting with classic 2 months ago Katie Chown
Tax notes for Furnished Holiday Lettings

Tax notes for Furnished Holiday Lettings

A brief outline of how tax works with your Furnished Holiday Let.

How to holiday let 10 months ago Kayleigh Hardy
Style Seminar: holiday cottage renovations

Style Seminar: holiday cottage renovations

Practical advice and inspiration for property owners and those thinking about a renovation project.

Interior design 1 year ago Caudwell & Co
Take action on climate change with the Winter Alliance

Take action on climate change with the Winter Alliance

Join the Winter Alliance in their campaign to tackle climate change with simple changes you can make to your holiday cottage now.

In the news 1 year ago Kayleigh Hardy

Hints and tips for holidays in the area

Free things to do on the Isle of Wight

Free things to do on the Isle of Wight

From dinosaur bone hunting to watching the red arrows, we've a great bunch of things to do for free on the Isle of Wight.

Things to do 3 days ago Liz Arnell
Top five Isle of Wight Christmas Markets

Top five Isle of Wight Christmas Markets

Find your festive feelings in November and December. With a Christmas market filling most weekends in the lead up to Christmas, you’ll be fully prepared for the big day by the time you head home from your Isle of Wight holiday.

Things to do 1 month ago Kayleigh Hardy
Child friendly Isle of Wight

Child friendly Isle of Wight

Hop on the steam railway, step back in time or get out on the water with our top child friendly things to do on the Isle of Wight.

Things to do 1 month ago Anmarie Bowler
The best pubs for a Sunday roast on the Isle of Wight

The best pubs for a Sunday roast on the Isle of Wight

Our island team are clued up on many things to do with the Isle of Wight but we like to think that food is their speciality. We put together this all important list of the best pubs to eat a Sunday lunch for the next time you fancy a cosy winter warmer.

Classic Fodder 2 months ago Kayleigh Hardy