Financial Matters Guest Communications Managing Your Vacation Rental New to Renting

Don’t let poor business practices result in lost bookings

5/5 - (18 votes)

A Fool Counting MoneyDespite your home being a perfect fit for a prospective vacationer, it’s possible that you can lose the booking due to an ill-advised booking procedure. A recent email correspondence with a vacationer drove home the risks of a homeowner requiring too much of a rental deposit, too soon, and without providing the vacationer with a lease in return.

The vacationer (from the UK) emailed us to ask about a particular homeowner who lists on our site.  She was looking for reassurance from us regarding the legitimacy of this owner.  I told her that the owner had been listing her home with us for the past two years and that we had received no negative comments about her or her home.  She went on to say that the owner had asked for 50% now and 50% as early as January 1 for a July rental, and she wondered if this was normal procedure.  I told her that the payment schedule is up to each owner and asked her if she had received a lease. She said that the owner had said she would send a lease but hadn’t yet.

A day or so after this correspondence, I received another email from the vacationer saying that, despite the good report I gave her about the owner, she had decided to rent another home.  This was her reasoning:  

I don’t want to pay 100% six months in advance, without proper documentation or security, so we are going for another house where the owner seems more businesslike with a proper booking form and lease.

It’s a shame that the homeowner lost a booking because she was asking for payment even before she sent the lease and because of an overly aggressive payment schedule.  See our advice about payment schedules.  The all-important trust between homeowner and vacationer had not been established during their initial communications.

Do you use a lease? Do you send it to your vacationers either before, or at least as soon as, you receive an initial payment from them? What’s been your experience with early bookings?

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About the author

Joan Talmadge

Joan Talmadge - My husband Jeff and I created in 1997, shortly after buying our Cape home. My background includes teaching fifth grade for 8 years and writing and editing educational publications for 15. I get great joy from helping fellow homeowners successfully rent their homes. Jeff and I are proud to have two of our three grown children working for, truly a family-run business. For me, the Cape and Islands are magical all times of the year -- whether it's walking on Nauset Beach, playing golf, or enjoying family and friends. Email Joan


  • Hi All,

    I have a two page lease/agreement that I send out to “serious” clients, I ask them to sign the lease and return it to me with a 50% deposit ASAP to hold the week, I ask them for full payment 14 days or sooner before their start date along with a $ 250 security deposit. When I receive full payment, I send them a signed lease back with a welcome packet that includes the back door code to enter and my WiFi code. This has worked well for me with no balks.
    I have never kept a security deposit other than from a Movie Production Company in 2012 that were slobs .

    My guests have been wonderful, even some college girls.

    Good luck to all.


  • Dear Shannon,

    If you could email us a copy of your lease, it would be very much appreciated. Points in this blog are appreciated also.

    We send out a (somewhat complicated) lease with a welcome/cover letter, and ask for half the rental fee, to reserve the week. We ask them to mail the signed lease with a check for the rental fee within 7 days. If there is no response in 7 days we contact them before placing the week back on the website. We ask for the remaining rental fee plus $125 security deposit 30 days before their week. We have smaller cottages, and $125 has seemed in keeping with our rental fees.

    Thank you.

    • Hi Karen. Certainly! Watch your inbox for the lease attachment. Thank you, also, for sharing your payment schedule and how well it has worked for you thus far!
      Best, Shannon

  • Great points Joan.

    I have had a lot of luck using services like airbnb/homeaway for my vacation home bookings as people seem to view them as reputable companies and trust when they put money down through their perspective websites. Obliviously there is a booking fee but it works pretty well for me overall.

  • I am wondering if you have a typical lease that is used for rentals and if you would share it

    Many thanks


    • Hi Carolyn. Happy to! I’ll send you the file by email. Just be sure to edit it to suit your needs before saving the file as your lease template. Best, Shannon

  • Hi Joan,

    I demand a 50% deposit to hold the booking dates. I immediately request a signed lease/agreemen at this time and then the full amount with $250 security deposit no later than 14 days prior to occupancy.
    This has worked well for me. Some want to send in the deposit right away, but I ask them to wait till after the new year, allowing me to keep all my financial data together for that year.

  • Hi Joan,
    I have been renting my home on your site for over 10 years. Last summer my family needed a ‘bridge’ week before we headed home. A great opportunity to visit another part of the cape we don’t usually frequent we thought!
    The rental was just awful! I could go on and on with details. We had to go to Walmart to buy lots of things just to stay the week (air freshener being one of them because of the terrible smell in the carpets.) The owners were apologetic but I really feel like I should have written a negative review to warn others- but I did not. What should I have done?

    • Hi Vicki. That’s a tough position to be in, so we were hoping to discuss your experience a little more offline, if you don’t mind. Watch for an email from myself or Joan with a few questions. Best, Shannon

  • We’ve been on weneedavacation for quite a few years and have not had any complaints about our payment requests. We ask $200 security upfront to reserve the week. This is returnable within 30 days after occupancy given no damage or problems. We’ve never had to keep a deposit. We send a lease agreement after Jan. 1 and ask for the signed copy returned by March 31 along with 1/2 of the rental fee. The other 1/2 is due 30 days before occupancy. I do usually send a reminder before each payment due date. We have a $75/per pet per week fee which is not returnable and included with the lease and 1/2 weekly fee. We are charged extra for cleaning when there is a pet and find the fee reasonable. We have had no problems or complaints. We have a tenant who returns 2 x each year and after 7 years we don’t ask for a security any more. We had 3 returning tenants already book for next summer plus new guests.
    We’ve had guests come from Canada, the U.K. and as far away as CA and FL. We are usually booked from May into Oct. We thank wnav for its great service and the opportunity to make our house available to so many to view. Plus, the site just keeps improving.
    Lynn McGarvey
    #14996, Dennis, MA

    • Hi Lynn! So glad to hear your payment schedule is working out for you and for your guests. The repeat bookings you’ve spoken of are proof! And thank you for your wonderful comments about our site and the personal service we provide. It is our absolute pleasure! Best, Shannon