Managing Your Vacation Rental

2021 Rental Season Checklist

Written by Elizabeth Weedon
2021 Rental Season Checklist
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Are you prepared for the 2021 rental season? As we navigate through the second season of the pandemic, here are the 10 most important issues for you to address:

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. So take a look by using the Listing Quality Audit link in your Homeowner Center. Eventually, we will be implementing a listing rating tied to the search results, and this rating will be based in part on the Audit. Read more about the Audit in Is Your Listing Up to Snuff? 

2. Get organized.

The key to successful rental management is being well-organized. The goal is to save yourself time and effort as well as provide your guests with a professional, trustworthy, and efficient experience with you. Here are some tips:

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! Ask what special precautions or measures they will be taking due to the pandemic. That way, you can alleviate concerns from your guests about contagion. And don’t forget your trash removal, landscapers, or any other service providers who help you throughout the rental season. Looking for assistance? Take a look at our Home Services Directory for providers right in your area.

4. Be sure you are in compliance with the MA Lodging Tax rules.

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? If you are unsure of what your tax rate is, your listing indicates the appropriate percentage of tax that would be applied to your rental.  For more information about the Lodging Tax, see our Lodging Tax FAQ’s.

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

Even if you have had no changes to your pricing or availability, it’s vitally 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  Vacationers who see an out-of-date calendar date stamp are apt to move on to another listing.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 Calendar.

6. Make sure your pictures are the best they can be.

Plenty of high-quality, current, large, pictures – and valuable, descriptive captions – are vital to the success of marketing your home. Period. See our blog post, The Ideal Listing: Visual Appeal.

7. Review your cancellation policy.

Due to the pandemic, many homeowners last year relaxed their cancellation policies significantly. Even if the COVID situation improves by this rental season, many vacationers are still very wary about losing their deposits if they are unable to get to your home. If your policy is relaxed, promote that on your listing so vacationers are incented to book with you. You might also encourage your guests to get travel insurance. will provide them with a choice of companies and policies. Read more about our cancellation policy advice.

8. Ask your past guests for guest reviews.

Did you get at least 1 or 2 guest 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 from your Homeowner Center) to generate an email to your past guests providing them with a button to easily submit their review. For information about how to solicit reviews from your past guests, view our blog post about soliciting guest reviews.

9. Indicate your payment method options on your listing.

Online payments have become very popular with vacationers – and they provide many free and safe advantages to you, too. 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.

10. Be especially communicative with your committed guests

Even though COVID 19 has much less of an impact on travel this summer, your guests are going to be uneasy about logistics and their ability to get to your home due to restrictions and health concerns. We ALWAYS advocate for good communication from homeowners, but now more than ever, it’s so important. Read more about Reaching out to your guests.

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. 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. Email Elizabeth