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Managing Your Bookings

Elizabeth Weedon | 2/14/2012 (updated 5/27/2021)
One of the most challenging aspects of renting a vacation home for us homeowners is the business side of managing your rental – what used to be referred to as the “paperwork.” Thankfully now, due to online tax preparation programs and online listing features like our  Booking Management system, the task can be accomplished much more easily and efficiently.

Keeping accurate records is critical!

Whether using an efficient, computerized program or doing things the old-fashioned way on paper, keeping thorough, accurate and up-to-date records is essential. Otherwise, you will risk the nightmare of double booking two parties, losing key tenant information, forgetting to send out documents, or losing track of what funds are due to you and when.

Key items to track

Among the most important items to retain and track for each booking throughout the booking and rental season are: •    The full name and contact information of each tenant, including any helpful anecdotal information. Be sure to obtain both an email address and cell phone number(s) if possible. •    The rate agreed upon for the rental period. •    The arrival and departure dates and, if possible, times (really helps in scheduling turnover cleaning/tasks). •    When you sent the lease out to your tenant. •    When the lease and initial deposit are due back from your tenant. •    When the final rental deposit is due. •    When the security deposit is due. •    When you need to send your tenant the keys, directions, instructions, etc. •    When you need to return the security deposit to your tenants after their departure. •    All of your expenses, including marketing/travel/repairs, for tax deduction purposes.

Online management is efficient and easily accessible

We urge you to use our free Booking Management feature. It’s not only tied directly to your listing’s pricing and availability calendar, it also helps you keep track of all the documents and funds, clearly showing when an item is overdue either to or from you. With it, you can retain information about the make-up of a party, names and ages of the kids, pets, special needs or arrangements, how they left the house, etc. And it can be accessed online from anywhere, unlike manila files of paperwork that never seem to be around when you need them. (The information you enter is private, though, and only visible to you or to anyone able to log in to your account with your username and password.) Do you have any “special tricks” for keeping track of your vacation rental tenants and bookings? Any “Oops!” stories to share?
About Elizabeth Weedon

About Elizabeth Weedon: I have worked for WeNeedaVacation.com since 2008, and I've been a loyal homeowner listed on the site since early 1998. An enthusiastic member of the Homeowner Support Team, I provide fellow Cape and Islands vacation rental homeowners with advice about online marketing and rental management techniques to ensure them a successful rental experience each season. In addition to phone and email support to our homeowners, I also create and edit much of the content on our website, as well as our Homeowner Blog and monthly newsletters. I am also the Press & PR Coordinator for the company, responsible for drafting our press releases and responding to press inquiries and interviews. I grew up summering on the Vineyard, where I have managed my family's rental home since the mid-1980's, and I'm passionately devoted to the Island. My husband and I live in Wellesley where we have raised our 2 grown kids and our Black Lab, Maisie.