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Tips to convert last-minute inquiries to bookings

Elizabeth Weedon | Updated 3/19/2025
Tips to convert last-minute inquiries to bookings
Anyone who still has availability late in the booking season is usually anxious to do what they can to fill the remaining vacancies. 

Time is of the essence!

Respond to inquiries as quickly as possible. Keep in mind that vacationers are anxious to complete their plans. They may be corresponding with different owners and on more than one property. They may be trying to coordinate with family or friends. Or they simply need immediate gratification. Regardless, they expect their questions to be answered ASAP.  You receive your inquiries via email. So, if it arrives at a busy time for you, you might email the vacationer right away anyway to let them know that you will be getting back to them very soon with a detailed response. Also, by enabling the Text Message Alert feature on your listing you will receive a text from us whenever you receive an email inquiry.    Don’t underestimate the power of a phone call. Speaking with someone directly is a much more personal connection. In fact, a phone conversation may make the difference between a vacationer booking your home over someone else’s with whom they have only communicated by email. Most vacationers include their phone number with their email inquiry. Speaking with the vacationer will help build a personal connection and establish trust. It will also help both you and the prospective guests determine if your home is a good fit for them. (Read our previous blog post about the Value of personalizing your rental business.) 

Don’t be afraid to be pro-active.

If you still haven’t heard back from a vacationer after responding to an inquiry – go ahead and follow up with them. What have you got to lose? Even if they’ve made other plans, at least you’ll know and can then focus on the next vacationer. 

Provide incentive.

Naturally, if you can offer a little something to sweeten the pot, that helps. If your listing is getting a lot of visibility (hits/views) and inquiries, but no one is committing, that’s usually an indication that they have found something comparable for less. Perhaps your home is a little nicer or the location a little better, but the vacationers might care more about saving some money. 

Promote a special offer.

An added benefit of offering a price reduction or last-minute deal is that it enables you to leverage it to attract more attention to your listing. Post a free “Owner Special” highlighting your offer. Or purchase a Last-minute Availability Alert to be included in our Last-minute Availability and Deals directory. Additional exposure has proven to boost inquiries by 60%! (See our post about using special offers to draw attention to your listing.)

Consider reducing your minimum stay requirement.

In recent years, we’ve noticed a growing demand from vacationers for shorter term rentals. If you can provide flexibility and shorter stays, you may end up filling your remaining vacancies. Naturally, this requires additional turnovers and the added time and effort of processing more bookings. On the positive side, vacationers are prepared to pay more per night for shorter stays of two or three nights.

Is your listing up to snuff?

Make sure your listing is as effective as possible to help bring you inquiries and bookings any time of year. Are your pictures large, horizontal, and good quality? Do you have plenty of recent guest reviews? Is your calendar’s date stamp current, assuring vacationers that the availability of your home is accurate? Is your listing’s Title and Property Description detailed, informative, and inviting? Is the pin on your listing’s Google Map where it should be?  Read more about marketing advice in our blog series, The Ideal Listing.
About Elizabeth Weedon

About Elizabeth Weedon: I worked for WeNeedaVacation from 2008 until I retired in 2023. I was also one of the first vacation rental owners on the site in early 1998, when I managed my family’s Vineyard rental home. An enthusiastic member of the support staff, I provided fellow Cape and Islands vacation rental owners with advice about online marketing and rental management techniques. I created and edited much of the content on the website, as well as blogs posts and monthly newsletters. I now live on Martha’s Vineyard full time with my family.

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