Managing Your Vacation Rental Miscellaneous

Successful vacation rental booking techniques

Written by Elizabeth Weedon
Successful vacation rental booking techniques
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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. Confirm the arrival and departure dates with the vacationer and their contact information.
  2. Tell them that you will be mailing them two copies of the lease signed by you with instructions for them to sign one and return it to you with the deposit – this can be either an initial rental deposit of 50% of the rental or, especially as the season nears, the full rent.  The remainder, including the Lodging Tax, if applicable, would then be due 30-90 days prior to their arrival (this is up to you).  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 checks up front with the signed lease.  (Read more about Payment Schedules.)
  3. Edit your lease to include the tenants’ names and addresses, arrival/departure dates, etc., and print, sign, and date two separate copies of the new lease. (Read more about leases or contact us to receive a sample lease.)
  4. Create a cover letter for the lease confirming their dates, whom to make the checks payable, any unusual issues involved with your property, etc.
  5. Mail the lease and cover letter to the prospective tenant. If the rental week is imminent, email the documents to them as well so that they can print, sign and return them to you sooner.
  6. Use our Booking Management system (see the link in your Homeowner Center), which enables you to retain and track:
  • the dates of each rental
  • your tenants’ names
  • 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 or rent)
  • the date you sent the directions/keys
  • the date you returned the security deposit after their stay
  • random notes about your guests with kids’ names, special requests, etc.

(Read more about booking management advice.)

  1. Return their security deposit as soon as possible after their departure.
  2. 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

Security Deposits

Withholding Security Deposits

Guest Reviews: Post ‘em or Weep

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 have managed my family's rental home there since the mid-1980’s. I’m passionately devoted to the Vineyard – and to, 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 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