Managing Your Vacation Rental

Successfully managing a vacation rental

Written by Elizabeth Weedon
5/5 - (3 votes)

There’s no question that today’s vacationer is more discerning and has greater expectations of both the homes they’re renting and the booking process itself than ever before. In order to meet those demands, it’s important for homeowners to provide as “frictionless” an experience as possible for their guests, before, during, and after their stays.

How can you up your management game?

  • Use templates for quick, professional, good quality responses to your guests. Your WNAV account provides the following templates to generate emails directly from your listing to:
    • reach out to past guests  for the following season
    • ask past guests for guest reviews
    • request permission from a guest to convert a homeowner-entered guest review to a vacationer-entered one
  • Take advantage of our Booking Management system to capture and track all of your bookings, when items are due or overdue, any special requirements of a guest, etc. We will be adding a line item for the lodging tax, too. It enables you to manage your rental more easily and professionally.
  • Respond to inquiries as quickly as possible. Vacationers expect immediate results, and waiting for 24 hours to respond is no longer adequate. (Read more about converting inquiries to bookings.)
  • Provide online payments options to your guests.

Keep your calendar up to date year round

In light of the growing trend towards an increase in early bookings over the past few years, we urge homeowners with active listings to make sure their 2020 pricing and availability have been entered. Don’t be overly generous to your repeat guests by holding off on opening your calendar and thus possibly miss out on inquiries from new guests.  And, naturally, any listings that are not even active year round are missing out on this wave of early inquiries and bookings.

Pricing tip

We strongly recommend you consider the benefits of “tiering” your weekly pricing in order to reflect the relative popularity of certain weeks.  The sweet spot of the summer on the Cape and Islands is the first 2 weeks of August, followed by the week on either side of those 2 weeks, with the first and last weeks of the season being  the most difficult for homeowners to fill.

Consider shorter stays

We’ve noted a growing demand from vacationers for shorter stays, particularly in the off- or shoulder-seasons. Vacationers are taking more vacations but of shorter durations.

For many homeowners, it’s not possible to turn over a home midweek or more often than they already do. But if you live locally or have a dependable turnover team, we recommend that you consider offering less-than-weekly stays, even in the summer. Naturally, you probably won’t fill every night of the summer, but at a higher nightly rate, your summer income may end up being the same as, or even higher, than if you rented by the week.

Successful marketing strategies

Given the amount of competition out there, providing great pictures and plenty of current guest reviews, although still critical, is no longer enough.

Our top 5 additional marketing tips:

  • Take advantage of the Listing Quality Audit in your Homeowner Center. It lets you know what might be missing or not optimal on your listing.  (Read more about Keeping Your Listing Up to Snuff.)
  • Reach out to former guests. This “low-lying fruit” has stayed in your home and proven to be a good fit. Perhaps entice them to return with a discount if they commit by a certain date. And feel free to contact past inquirers, too. Even if they didn’t end up booking your home, it must have met their search criteria at some point.
  • Use all the resources you can:
    • Owner Specials: They’re free and can be posted at any time of the year to highlight a special offer or price reduction and draw attention to your listing.
    • Last-minute Availability Alerts: A fee-based feature, they provide greater exposure to your listing and any last-minute offers you wish to promote (only available during from May-September).
    • About the Owner: An opportunity for vacationers to make a personal connection with you and for you to provide them with a more personal perspective on your property.
    • Social Media: an easy, free way to provide greater exposure to your listing.
  • Share our content with your guests and on social media.  Your guests will appreciate the helpful tips. And the more people hear about us through social media, the more vacationers will use us to find their vacation rentals. So promoting us helps you. Here are some examples of the great content we offer:  EsCape TV episodes, Vacationer Blog, The Vacation Planner.



About the author

Elizabeth Weedon

Elizabeth Weedon - Although I’ve worked for 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 managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to WeNeedaVacation, which I credit with enabling me to hold onto the special property that has been in our family for nearly a century. An enthusiastic member of the WNAV Homeowner Support Team, I endeavor to keep my finger on the pulse of the Cape and Islands vacation rental industry so that I can provide homeowners advice about how to ensure their booking success with us. With owner Joan Talmadge, I am also responsible for editing and writing much of the text on our website, our monthly newsletters, and Homeowner Blog posts.