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Thinking of turning your Kent second home into a holiday let?

30 September 2026
Phoebe Shipton

A second home can be both a place you love spending time and somewhere other people enjoy discovering. Holiday letting can help contribute towards running costs, while allowing you to continue using it yourself with family and friends. Making it work successfully starts with understanding what you want from the property and what welcoming paying guests will involve.

At Keepers Cottages, we work with holiday homes across Kent, from coastal cottages to larger countryside houses. Here are the questions we recommend exploring before you start welcoming paying guests.

Decide what you want holiday letting to achieve

Are you hoping to cover some household bills, generate a regular income or make better use of a home that stands empty for much of the year?

Your answer shapes the decisions that follow. If family holidays remain your priority, begin by deciding which dates you want to keep. If income is the main objective, you may want to make more of the most desirable weeks available to guests, such as Easter, Summer and Christmas.

Neither approach needs to be fixed forever. What matters is that your income expectations reflect the dates you genuinely plan to offer. At Keepers Cottages, we take the time to find out what owners are looking to achieve, and tailor our approach to suit this.

Consider who would choose your property

A good holiday home gives guests a clear reason to book. That might be a walkable location into the nearest town or village, easy beach access, a hot tub, a games room, or space for a family gathering.

Look beyond the bedroom count. Is there comfortable seating for everyone around the dining table and in the living areas? Can guests eat outside together? How straightforward are parking, luggage drop off and arrival after dark?

These details help establish who the home suits. A compact cottage with steep stairs might be lovely for a couple, but it’s important that the description is clear so that guests can judge its suitability for young children or limited mobility.

Getting an income proposal before committing to improvements

An honest and realistic income proposal can help you understand the property’s potential and which changes deserve the extra budget.

At Keepers Cottages, we will provide an annual income appraisal that considers seasonality, your own stays and comparable homes. A headline summer weekly rate tells you very little about the income over a full year.

It is also helpful to ask what could limit bookings. For example, an awkward bedroom arrangement with no space for bedside tables and lights, or limited parking options, may warrant attention before you commit to any decorative improvements.

Check permission and safety regulations before taking bookings

Confirm that your mortgage, lease and any relevant restrictions allow holiday letting. Ask your local planning authority whether consent is needed for your proposed use, and arrange insurance suitable for paying guests.

You will also need to address the property’s safety requirements. Our guide to holiday let rules in England explains the main areas to work through, with a separate article on fire safety.

It is essential to plan and consider these checks before deciding a launch date than to discover this later on when you have guests due to stay.

Sarah, the head of property management at Keepers Cottages, at Downs Cottage in Kingsdown

Decide how the property will be managed

Self-management involves everything from the initial enquiries, pricing decisions, payment handling, guest questions and organising each changeover. It also means having suitable out of hours support as well as a back up plan for when things inevitably go wrong.

If you are considering letting with an agency, find out exactly what the service includes. Marketing and booking support is different from a service that also coordinates housekeeping and linen. Establish who will arrange repairs, approve spending and respond outside office hours.

The right arrangement should suit where you live, how involved you want to be and the support your home needs.

Take the first step with local advice

You do not need every answer before having an initial conversation. Knowing your likely availability and plans, your goals and the property’s current condition gives us a useful starting point.

If you are considering holiday letting in Kent, speak to the Keepers Cottages team about your home. We can discuss its potential and the practical steps involved in preparing it for guests.

Download our Guide to Letting

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Frequently Asked Questions

Yes, you can plan owner stays around guest availability. You will have access to an owner portal, meaning you can block dates out as you wish. The dates you reserve may affect your income potential, so it’s worth mentioning them when discussing a rental appraisal.

Not necessarily. Start with safety, condition and guest comfort. We can advise and help you decide whether small improvements would be more useful than a full refurbishment.

Your local planning authority will decide whether you need planning permission. The UK government is introducing a registration scheme for short-term lets across England in 2026. At Keepers Cottages, we can guide you through this.

For holiday letting in the England, you will need dedicated holiday let insurance, public liability cover and building and contents cover suitable for short-term letting. You should also check the specific rules around holiday let insurance in your local area.

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About Phoebe Shipton

Having studied Marketing at University of Manchester, Phoebe joined the family business in 2020 as Head of Marketing and Operations. Phoebe is focused on making Keepers Cottages stand out, as well as ensuring the bookings flood in!

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