Managing Your Vacation Rental

Managing Your Bookings

Written by Elizabeth Weedon
4.9/5 - (18 votes)

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 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.


  • I feel like we never leave our ‘little piece of heaven’ in Brewster. I love being on Sheep’s Pond, but sometimes I would like to experience another part of CC for a few nights. Would anyone be interested in trading a few nights in late June? My rental is #4136

  • I am fairly new to this renting life. We bought our 2nd home on MV last May, and all but 2 of last summer’s rentals were in place at the time of the sale. We don’t rent our other home. I think that I’m organized for this year, with just 2 weeks unrented, and 2 “tentative weeks. I have a new cleaning crew this year, who I was able to contact after the home owner forum on the Vineyard last fall. I’m still nervous that I’m forgetting things, or will forget. I love the booking management section of your website. It seems complete, as long as I update it. I’m hoping that by next summer, I will feel more comfortable with it all. We are in the process of updating our home, so that adds another whole issue, to be sure that I am offering all that I can without doing too much. Thanks for the blog and all the help.

    • Gosh, Kathy, it sounds like you’re doing a great job! Did you hear of the housekeeper at our Homeowner Forum in Vineyard Haven last fall? I’m planning to write a couple of blog posts about housekeeping soon: issues such as how to procure a good one, what to avoid, setting clear expectations, etc. Stay tuned! I’m glad you’re using the Booking Management feature – I LOVE it! Especially the way it allows me to retain anecdotal info about my tenants such as the ages of their kids, special requirements, etc. Plus, how it helps me keep track of what documents or monies are due when. I don’t think many of our homeowners are using it yet, and I often wonder why. You sound like such a responsible, hardworking and diligent homeowner! I’m sure your tenants are very appreciative of all your efforts. Keep up the good work!

      • At the fall forum, which I found to be extremely helpful, I asked if anyone had any suggestions of cleaners, since I had to let my first one go, and I used another for the rest of the summer, but being on MV, I’m not sure that she is there legally. I don’t want to be part of that problem, and couldn’t decide how to go about finding an American or at least legal house cleaner. A home owner gave me the name of his cleaner, I contacted her, met with her, and she’s my new one. After the incident with my first person, I was beginning to wonder if the renting idea was a bad one. I’m hoping for a less stressful summer, and your website is so helpful in that respect.

        • I’m so glad to hear that the new house cleaner situation worked out well, Kathy, and that you found the Homeowner Forum and our site helpful!! That’s what we’re here for! Good luck this summer!