Managing Your Vacation Rental

A Quick Guide to Vacation Rental Management

Written by Elizabeth Weedon
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Managing a vacation rental property can – and should – be a very rewarding process. But it shouldn’t be done on a whim without careful planning and preparation. It’s vitally important to do it right!

We have compiled an eBook entitled “Your Online Listing Is Active – Now What?! as a guide for seasoned rental management veterans and newbies alike. Here is a brief outline of the eBook’s contents.

What could go wrong?

One of the best ways to assure your success is to be aware of the potential pitfalls to avoid. Naturally, these include the risk of damage to your home (actually an incredibly rare occurrence). But it’s also extremely important that you assure the comfort and happiness of your guests. This starts by screening them properly to assure your home is a good fit for them. We provide a number of other simple but effective strategies to avoid a negative guest review and increase the likelihood that they will return the following season.

Screening your prospective tenants

This very first interaction with your prospective guests is crucial. Not only are you trying to fill an open week and make sure that the party inquiring isn’t a group of young adults looking for a “party” house. But you are also conveying to the vacationer a very honest and accurate description of your home and its location. In so doing, trust in you is built and their expectations are managed to prevent disappointment on their arrival. In the eBook, we provide some strategies to help you with this process. Read more about Screening prospective tenants and Screening tenants II: It’s OK to say No.

Payments schedules

The most common, accepted practice is to request half of the rental amount at the signing of the lease and the balance within 45-90 days prior to your guests’ arrivals.  The Lodging Tax and any fees you charge are usually collected with the balance of the rent. If, however, the booking takes place beyond May 1, it’s not unusual to require full payment at the signing of the lease, including the tax and any fees. The Security Deposit is not due until one month prior to your guests’ arrivals. Read more about Payment Schedules.

Accepted means of payment still includes the old-fashioned personal check, requiring no fees from either party.  But there are also advantages to both you and your guests of accepting online payments such as credit cards through PayPal, online bank transfers (ACH/EFT), or other funds transfer options such as Venmo, Zelle, GooglePay, etc.  Keep in mind that some of these online options require a fee, usually of the “vendor” (you). Read our post about Online Payment Options for Your Guests.

The lease

We believe that using a lease contract is extremely important. Not only does it provide legal protection for both parties, but it is crucial to avoid misunderstandings and controversies, which, in turn, can lead to negative guest reviews or even law suits. If you don’t have a good one, we will be happy to provide you with a copy of our sample lease. Read more about The Lease.

Creating a booking management system

Using a good booking management system enables you to avoid pitfalls (such as double bookings) and helps you establish an efficient and seamless booking and record-keeping process. Your subscription includes a free Booking Management feature allowing you to record as much information as possible, track communications/leases/funds, and even provide you with weekly reminders of upcoming or overdue items. Read more about Booking Management Made Easy.

Setting up your rental management team

Some of you may prefer to “go it alone” in your management of the property before and in between your guests’ arrivals. But many of you do not live near your rental homes and require professional assistance from such service providers as housecleaners, landscapers, trash removal, etc. If so, don’t delay! Set up your management team as soon as you can, choosing the most reliable services you can.

Homeowners listed with us have access to our Home Services Directory, which provides contact information to services in your vicinity. Read more about setting up your service provider team.

Make it personal

Although vacation rental management is most certainly a business (and should be conducted as such), creating a strong personal connection with your guests is a key ingredient in the recipe for success. And it’s more fun for you, too!

Enabling your guests to get to know you creates a much deeper level of trust and accessibility. They are more likely to “roll with it” if something should go amiss while they’re at your home (the dishwasher breaks, the roof leaks, etc.). But it also increases your odds of their submitting a glowing guest review after their departure – which is crucial to your marketing success for subsequent seasons.

Just prior to your guests’ arrival

Don’t just assume everything is all set for your guests and that they’re on their own in getting to your home. Check in with them 5 to 10 days prior to their arrival to remind them of what to bring (towels, for example, if you don’t provide them) and what not to bring (paper/cleaning products if you do provide them). Make sure they have the address and/or directions to your home and instructions on how to get in (or a key or entry code, etc.). And ask if they have any last-minute questions or requests.

After your guests have arrived

Sorry, but it’s not over, even after they’ve finally arrived. We strongly urge you to check in with them either by text or, preferably, a phone call to make sure they are finding everything to their liking, know where things are, and don’t have any questions or concerns.

SO often when a problem arises, it could so easily have been avoided if the homeowner had checked in with their guests in this way and averted a misunderstanding or minor issue that can fester with the vacationer all week. And it’s another opportunity to show them that you care about their comfort and happiness. Read more about Welcoming Your Guests.

After their departure

Your final responsibilities with each guest is, first, to return their security deposit as quickly as possible.  Then, follow up with an email notifying them that you have done so, thanking them for leaving your home in good condition, and, most importantly, requesting that they submit a guest review to your listing! Naturally, you might also see if they have any interest in returning the following season. Read more about Soliciting Guest Reviews.


None of what we have outlined here requires a ton of time, effort, or expense. But following these guidelines will assure a successful and rewarding experience for you for years to come. If you manage your vacation rental well, you will be able to market it well for future rental seasons. For more in depth information, read the eBook or any of our many blog posts related to managing and marketing your vacation rental home.

Read Our E-Book

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.