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Vacation Rental Checklist for Homeowners

Elizabeth Weedon | 2/1/2019 (updated 3/1/2024)
Updated March 2024 The rental season will be here before you know it!  Are you ready?  Here are the top 10 things to keep in mind as you make your preparations. 

1. View your Listing Quality Audit

Your Listing Quality Audit is for your eyes only and details the aspects of your listing that are in good shape and the ones that need improvement. The Listing Rating, which is based on the Audit, is tied to the search order results.  The better your Rating, the higher your listing will appear in the search results. So, look at the Listing Quality Audit link in your Homeowner Center. Read more about the Audit in Is Your Listing Up to Snuff? 

2. Take advantage of our Booking Management feature

It truly IS easy! Using this feature in your account allows you to conduct your rental management business with accuracy and professionalism. It helps you take notes about your guests and track their payments. You can even schedule reminders to be sent when a payment is imminent or overdue. And using Booking Management helps prevent double bookings! See more about managing your bookings with ease.

3. Set up your service providers for the season

It’s never too early to confirm your turnover schedule with your housecleaners who are so vital to your success in renting! And don’t forget your trash removal, landscapers, or any other service providers who help you through the rental season. Take a look at our Home Services Directory for providers in your area.

4. Communicate with your guests

Nothing is more important to your success than communicating with your guests every step of the way. Establishing a personal relationship with them during the booking process will set the tone for their experience. And then continue the communication before, during, and after their stay.  Read more about the importance of Reaching out to your guests.

5. Be sure you are in compliance with the MA Lodging Tax rules and your town’s regulations

Is your home registered with the MA Dept. of Revenue? Is it covered for at least $1M in liability insurance? Does your lease include a line item for the tax? The tax rate for rentals in your town is posted on your listing.   For more information about the Lodging Tax, see our Lodging Tax FAQ’s.  Your town may also require a separate registration and fee. See a list of the towns that currently require registration.

6. Keep your calendar up to date at least every 2-3 weeks 

Even if there are no changes to your pricing or availability, it’s important to keep your listing’s date stamp as current as possible, indicating to vacationers that your pricing and availability information is accurate. Vacationers who see an out-of-date calendar date stamp are apt to move on to another listing. Take a look at 5 Crucial Reasons to Update Your Calendars. 

7. Make sure you have current and high-quality pictures with descriptive captions

Large, bright, and attractive pictures will lead to more inquiries. Vacationers spend about 8 seconds on a single listing, and if your pictures don’t grab them . . . off they go to look at the next listing. See our blog post, The Ideal Listing: Visual Appeal. 

8. Review your cancellation policy

Many vacationers are very wary about losing their deposit if they have to cancel the booking. If your policy is relaxed, promote that on your listing so vacationers are incentivized to book with you. You might also encourage your guests to get travel insurance. TravelInsurance.com will provide them with a choice of companies and policies. Read more about our cancellation policy advice. 

9. Ask your past guests for reviews

Did you get at least a few reviews from your guests last summer? If not, it’s not too late to ask them!  Use the Guest Review Request Form (see the tab on your Guest Reviews page in your Homeowner Center) to generate an email to your past guests providing them with a button to easily submit their review. See more about soliciting guest reviews.

10. Indicate your payment method options on your listing

Online payments are becoming increasingly popular with vacationers, so why not distinguish your listing by promoting this attractive option? Add the forms of payment you accept to the Payment Methods section near the bottom of your calendar page. Read more about Online Payment Options that you can offer your guests.  [mks_one_half] [mks_button size="medium" title="Homeowner Login" style="rounded" url="https://www.weneedavacation.com/HC/HCWelcome.aspx" target="_self" bg_color="#045a93" txt_color="#FFFFFF" icon="" icon_type="" nofollow="0"] [/mks_one_half] [mks_one_half] [mks_button size="medium" title="List Your Property" style="rounded" url="https://www.weneedavacation.com/Help/Why-List-Your-Vacation-Rental.aspx" target="_self" bg_color="#045a93" txt_color="#FFFFFF" icon="" icon_type="" nofollow="0"] [/mks_one_half]
About Elizabeth Weedon

About Elizabeth Weedon: I have worked for WeNeedaVacation.com since 2008, and I've been a loyal homeowner listed on the site since early 1998. An enthusiastic member of the Homeowner Support Team, I provide fellow Cape and Islands vacation rental homeowners with advice about online marketing and rental management techniques to ensure them a successful rental experience each season. In addition to phone and email support to our homeowners, I also create and edit much of the content on our website, as well as our Homeowner Blog and monthly newsletters. I am also the Press & PR Coordinator for the company, responsible for drafting our press releases and responding to press inquiries and interviews. I grew up summering on the Vineyard, where I have managed my family's rental home since the mid-1980's, and I'm passionately devoted to the Island. My husband and I live in Wellesley where we have raised our 2 grown kids and our Black Lab, Maisie.

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