Managing Your Vacation Rental

Successful vacation rental booking techniques

Written by Elizabeth Weedon
5/5 - (8 votes)

BookingProceduresSo, you’ve received a promising inquiry for your rental home – now what?! Presumably, you have read our tips about screening prospective tenants to assure a good fit for your home. But what do you do once they commit to renting your property?

The following is a quick overview of our recommended standard procedures for booking your home:

  1. Rental dates and contact info: Confirm the arrival and departure dates with the vacationer, and be sure to get their contact information, including at least one cell phone number.
  2. The lease: If you mail your leases, tell them that you will be sending them two copies of the lease signed by you with instructions for them to sign one and return it to you with the deposit.  If you email your leases, you would ask that they print it, sign it, scan it, and email it back to you as soon as possible. (Read more about leases or contact us to receive a sample lease.)
  3. Rental deposits, fees, and the lodging tax:  If it’s early in the booking season (before May 1), the rental deposit is usually an initial deposit of 50% of the rent and collected with the signed lease. The remainder, including the Lodging Tax and any cleaning or other fees, if applicable, would then be due 45-90 days prior to their arrival (this is up to you). But if the booking occurs just prior to or during the rental season (after May 1), you should collect the full rent, the lodging tax, and any fees at the time of booking.
  4. The security deposit (very different from the rental deposit) is due just one month prior to arrival. If it is at a late point in the season, though, it’s reasonable to ask for both the rent/tax and the security deposit payments up front with the signed lease.  (Read more about Payment Schedules) and
  5. Create a cover letter for the lease confirming their dates, your payment instructions, any unusual issues involved with your property, etc. You should have a template of this lease cover letter/email.
  6. Send the lease and cover letter to the prospective tenant. If the rental week is imminent, email the documents to them rather than mail it so that they can print, sign, scan, and return them to you sooner.
  7. Use our Booking Management system (see the link in the Guest Tracker section of your Homeowner Center), which enables you to retain and track:
  • the dates of each rental
  • your tenants’ names
  • random notes about your guests with kids’ names, special requests, etc.
  • the date the lease was mailed/emailed
  • the date your receive the check and lease
  • the date you receive the remainder of the funds (security deposit, tax or rent)
  • the date you sent the directions/keys
  • the date you returned the security deposit after their stay

You can also enable the Booking Management system to send you weekly email reminders about when there’s something for you to do or if you need to remind your guests for the next payment, etc.  Read more about the Booking Management system.

8. Return their security deposit as soon as possible after their departure.

9. Send a Guest Review Request Form immediately after you return the security deposit.

Other helpful links:

Screening tenants for a good fit

Screening tenants II: It’s OK to say No

Payment Schedules

Managing Your Tenants’ Expectations

10 Tips to Acquire Positive Guest Reviews

The Lease

Those Special Touches

Personalizing your rental business

Linens: Should you provide them?

Cleaning fee pros & cons

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.