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Vacation Rental Checklist for Hosts

Samantha Williams | Updated 1/9/2026
Vacation Rental Checklist for Hosts: Get Ready for the Rental Season

The rental season will be here before you know it! Are you ready? This vacation rental checklist for hosts outlines the 10 most important steps to prepare your short-term rental for success. From optimizing your listing and managing bookings to staying compliant and delivering a great guest experience, these tips will help you attract more bookings and start the season strong.

1. Review Your Listing Quality Audit to Improve Search Visibility

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 improving your vacation rental listing quality in Is your listing up to snuff? Check your Listing Quality Audit!

2. Use Booking Management Tools to Stay Organized and Prevent Double Bookings

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. Using Booking Management helps prevent double bookings!

Learn more about managing vacation rental bookings with ease.

3. Confirm Housecleaning and Other Service Providers Before the Season Starts

It's never too early to confirm your turnover schedule with your housecleaners who are so vital to your success in renting! Don’t forget your trash removal, landscapers, or any other service providers who help you through the rental season.

Find trusted vacation rental service providers in our Home Services Directory.

4. Communicate Clearly With Guests Before, During, and After Their Stay

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. Continue the communication before, during, and after their stay.

Read more about the importance of Reaching Out to Your Guests.

5. Ensure Compliance With Massachusetts Lodging Tax and Local 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.

Get answers in our Massachusetts vacation rental lodging tax FAQs.

See a list of Massachusetts towns requiring vacation rental registration.

6. Keep Your Vacation Rental Calendar Updated 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. Use High-Quality, Up-to-Date Photos With Descriptive Captions

Pictures are one of the first things vacationers notice when browsing listings. High-quality, up-to-date photos with descriptive captions help your property stand out and set expectations for your guests. Update your images to reflect any improvements or changes you’ve made to your home.

Find tips in our Photography Guide for hosts.

8. Write a Detailed and Accurate Vacation Rental Description

Review your listing description to ensure it highlights the best features of your property and includes any updates or amenities you’ve added. A clear and inviting description can significantly impact a vacationer’s decision to book your home.

See more about crafting the perfect description in our Listing Description Guide.

9. Promote Special Offers and Discounts to Increase Bookings

Offering promotions or discounts during the off-season or for longer stays can attract more bookings. Highlight these offers in your listing and update them as needed.

Learn more about pricing strategies in our Pricing Tips and Tricks.

10. Stay Informed About Vacation Rental Industry Trends

The vacation rental market is always evolving. Keep up-to-date with trends, guest preferences, and industry news to remain competitive.

Visit our Vacation Rental Host Blog for insights and updates.

About Samantha Williams

About Samantha Williams: I've lived on Cape Cod since 2002, when my husband's service with the Coast Guard brought our family here, and it has felt like home ever since. As Director of Client Services, I oversee our support staff, guide projects, and collaborate on website development to keep our services growing for homeowners and vacationers. Outside of work, I enjoy life in Barnstable Village with my husband and our two grown daughters.