Managing Your Vacation Rental

Tips to retain repeat guests and attract new ones

Written by Elizabeth Weedon
Tips to retain repeat guests and attract new ones
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This rental season on the Cape and Islands has been unlike any others in our 21-year history. The vacation rental market had already become increasingly more competitive over the past few years, with record numbers of homeowners renting out their properties.

This year vacationers had a huge incentive to sign a lease before Jan. 1, thereby avoiding the tax.  They also had the option to vacation prior to July, and avoid the tax that way. Next year is a whole new ball game as there will be no options to avoid the tax.

In order to remain competitive, the average homeowner needs to pay attention to changes in the industry and make adjustments rather than stick with the status quo.

What you do during this rental season will affect next season’s bookings. Here are some suggestions:

Solicit as many guest reviews from this year’s guests as possible

Having guest reviews on a listing has become vital to the success of marketing your home!  Vacationers often move on to another listing if they don’t see any.  Guest reviews will significantly increase the number of inquiries and bookings you will get.

Make it personal

Although vacation rental management is most certainly a business (and should be conducted as such), creating a strong personal connection with your guests is a key ingredient in the recipe for success. Enabling your guests to get to know you creates a much deeper level of trust and accessibility. They are more likely to “roll with it” if something should go amiss while they’re at your home (the dishwasher breaks, insect issues, etc.). But it also increases the odds of their submitting a glowing guest review after their departure – which is crucial to success for subsequent seasons.

Just prior to your guests’ arrival

Don’t just assume everything is all set for your guests and that they’re on their own in getting to your home. Check in with them 5 to 10 days prior to their arrival to remind them of what to bring (linens and towels, for example, if you don’t provide them) and what not to bring (paper/cleaning products if you do provide them). Make sure they have the address and/or directions to your home and instructions on how to get in. And ask if they have any last-minute questions or requests.

After your guests have arrived

Sorry, but it’s not over, even after they’ve finally arrived. We strongly urge you to check in with them either by text or, preferably, a phone call to make sure they are finding everything to their liking, know where things are, and don’t have any questions or concerns. SO often when a problem arises, it could so easily have been avoided if the homeowner had checked in with their guests in this way and averted a misunderstanding or minor issue that can fester with the vacationer all week. And it’s just another opportunity to show them that you care about their comfort and happiness.

After their departure

Your final responsibility with each guest is to return their security deposit as quickly as possible and then follow up with an email notifying them that you have done so, thanking them for leaving your home in good condition, and, most importantly, requesting that they submit a guest review to your listing! Naturally, you might also see if they have any interest in returning the following season.  You might even provide them with some sort of incentive to book early.

About the author

Elizabeth Weedon

Elizabeth Weedon - Although I’ve worked for WeNeedaVacation.com since 2008, I’ve been a loyal homeowner on the site since early 1998, just a few months after the website was launched by the Talmadges. I grew up summering on the Vineyard and have managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to WeNeedaVacation.com, which I credit with enabling me to hold onto the special property that has been in our family since the 1920’s. An enthusiastic member of the WNAV.com Homeowner Support Team, I am particularly involved with our new listers, providing assistance with the sign-up process and advice about how to create the most effective listing to ensure their booking success with us. I have recently taken over our press and public relations needs. And, with owner Joan Talmadge, I am also responsible for editing and writing much of the content on our website, our monthly newsletters, and the blog posts. My husband and I live in Wellesley where we have raised our 2 grown kids and our Black Lab, Maisie. Email Elizabeth

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