Holiday letting insurance is usually bought property by property and then outgrown. Once there is more than one cottage, a cleaner on the books, a booking platform taking payment and a changeover team with keys, the thing being insured has stopped being a building and started being a business. The cover that fits at that point is a commercial policy with a property schedule, and moving to it usually costs less than running several separate policies.
When one policy per property stops making sense
Separate policies mean separate renewal dates, separate excesses, separate claims histories and a different insurer arguing each time something goes wrong. A portfolio or commercial holiday letting policy puts the properties on one schedule with one renewal, one excess structure and one point of contact. It also allows a single public liability limit across the business, which is what a booking platform or a corporate client will ask to see.
People, and the cover that follows them
A cleaner, a changeover team, a handyman on call or a caretaker are almost always employees or labour only subcontractors for insurance purposes, and employers liability is compulsory once anyone other than the owner works for the business. It is worth checking rather than assuming: paying somebody in cash for changeovers does not put them outside the definition, and the penalty for having no employers liability cover is charged for every day without it.
The platform does not insure you
Booking platforms offer host guarantees and damage protection schemes, and those are useful. They are not insurance contracts in the ordinary sense, they carry conditions and exclusions of their own, and they do not answer for the building, for loss of income after a fire, or for a guest's injury claim against you. Read them as a supplement to a policy, never as a replacement for one.
What a growing letting business should re examine at renewal
The rebuild figures on each property, which drift badly on older stone buildings. The liability limit against what platforms and any corporate lettings require. The loss of income period, which should reflect how long a real rebuild would take rather than the twelve months most policies default to. Whether the contents sums insured still match what has been replaced and upgraded since the last renewal.
Questions people ask about holiday letting insurance
Can I put several holiday lets on one policy?
Yes. Portfolio and commercial holiday letting policies carry a property schedule, and most insurers will write from two or three properties upwards. It is usually cheaper and always simpler than separate policies.
Do I need employers liability for a cleaner?
Almost certainly yes if they work for your business, and it is compulsory cover with a daily penalty for not holding it. The test is the working relationship rather than how they are paid.
Does a host guarantee from a booking site replace insurance?
No. It is a limited damage protection scheme with its own conditions, not a policy covering the building, the loss of income or your liability to a guest.
Should the properties be in a company?
That is a tax and finance question rather than an insurance one, but the insurer needs to know who the insured is. If the properties are held by a limited company, the policy should be in the company's name.