6 steps to creating a vacation rental newsletter

TL;DR: Build a contact list from past guests and inquiries, define newsletter value beyond promotions, create themed content, use email marketing tools with segmentation, set a consistent schedule, and get explicit opt-in consent. Newsletters convert warm leads into repeat bookings without cold advertising spend.

It can take a bit of effort to reach someone who wants to book your vacation rental. You need to get that visitor to your website, attract their attention on a channel or entice them through social media.

Don’t let all your hard work attracting new guests go to waste. Harness the power of email marketing to put yourself in front of your warm leads – anyone who has stayed with you before or inquired about your property in the past.

In six steps, we’ll teach you how to build a short-term property management newsletter that will reward you with repeat visitors and less vacancies.

Step 1: Build your contact database

Data field	Why you need it	Segmentation use
First name	Personalization in subject lines	N/A
Last name	Full guest identification	N/A
Email address	Delivery	N/A
Booking date	Timing for anniversary campaigns	“You stayed with us last March — book again?”
Trip purpose	Targeted content	Family travel tips vs. business traveler perks
Property booked	Location-specific offers	Mountain cabin guests get ski season deals

This step can be time-consuming depending on how well you’ve managed guest data in the past, but it will be Start with the last 12 months of guest data and inquiries. Anyone older than a year is closer to cold than warm — focus your initial effort where conversion probability is highest.

Export data from your property management system. If you’ve been operating without centralized records, manually compile from:

• Confirmation emails
• Inquiry messages on OTA platforms
• Direct booking records
• Payment system transaction logs

Create a spreadsheet or CRM with the fields above. This is tedious work. It’s also the foundation of every dollar you’ll make from repeat bookings. Do it once, maintain it going forward.

Use Guesty’s CRM to automatically collect and store guest data from every channel — Airbnb, Vrbo, Booking.com, direct bookings, and inquiries. Tag guests based on their stay patterns, add notes about preferences, and view complete reservation history in one place. When it’s time to export your contact list for email campaigns, you’ll have clean, organized data ready to segment.

Step 2: Define your newsletter value proposition

Nobody opens promotional emails anymore. Inboxes are full. Attention is scarce. If your newsletter is just “Book now, 15% off,” you’ll get marked as spam.

Create content your audience actually wants:

• Local event calendars for your destination (weekend festivals, concerts, seasonal attractions)
• Travel tips specific to your market (best hiking trails, restaurant recommendations, off-season activities)
• Property updates that improve guest experience (new amenities, renovations, upgraded features)
• Exclusive offers that reward loyalty (early booking access, repeat guest discounts)

The formula: valuable content first, booking opportunity second. Give them a reason to open the email that isn’t a sales pitch. Then position your property as the natural solution.

Example: “5 Winter Festivals in [Your City] This February” with a closing note: “Planning a trip? Our downtown loft puts you walking distance from all these events. Book before January 31 for 10% off.”

The content justifies the open. The offer captures the conversion. Skip the content and your open rates will tank.

Don’t let all your hard work attracting new guests go to waste. Your newsletter keeps you visible to people who already expressed interest.

Step 3: Create themed content that positions your properties

Now that you know what the purpose of your newsletter is, it’s time to create content. It will be helpful to use a theme for your newsletters. Here are some examples of themes that you can feel free to use:

Newsletter theme	Content angle	Property tie-in
Seasonal events	Local festivals, concerts, markets	“Our property is 5 minutes from the venue”
Travel tips	Packing guides, budget hacks, family activities	“Guests who stay with us save on [specific expense]”
Stress management	Vacation benefits, work-life balance	“Book a mid-week escape — our rates drop 30% off-season”
Destination weddings	Venue ideas, accommodation logistics	“We host wedding parties — 3+ rooms, custom group rates”

Tailor your primary content around that theme. A focus on stress management, for example, could feature an article about how vacation time can boost productivity, with a coupon for a stress-busting mid-week getaway. 

Each newsletter should include:

• One primary content piece (400-600 words) that provides genuine value
• 2-3 supporting elements (local tips, property updates, guest testimonials)
• One clear call-to-action (view availability, book direct, claim discount code)
• Contact information (website, email, phone, property address)
• Social proof (recent 5-star reviews, occupancy milestones, guest photos with permission)

Write the content first. Add the promotion last. The content is why they opened the email. The promotion is what converts them after you’ve delivered value.

Your spreadsheet from Step 1 becomes your contact list. Most email marketing platforms import CSV files directly.

Evaluate platforms based on:

• Segmentation capabilities (filter by booking date, property type, guest preferences)
• Automation features (anniversary emails, seasonal reminders, abandoned inquiry follow-ups)
• CAN-SPAM compliance (required by law — must include physical address, unsubscribe option, and ad identification)
• Template quality (mobile-responsive designs that don’t look like spam)
• Analytics tracking (open rates, click rates, conversion tracking)

Integrate Guesty’s CRM with Mailchimp to automatically sync guest data from all platforms into targeted audiences. When someone books, their information — stay dates, property preferences, booking channel — flows directly into your segmentation lists. Export targeted segments for campaigns: winter guests for your spring promotions, family travelers for kid-friendly activity guides, or business travelers for weekday discount offers.

Guesty’s Mailchimp integration handles the technical work. You create audiences based on actual guest behavior: last stay date, average review rating, total bookings, or property location. Schedule campaigns triggered by these segments, and your newsletter runs on autopilot while you manage operations.

Most email marketing platforms force you into CAN-SPAM compliance automatically. This federal law requires you to:

• Identify your message as an advertisement
• Include your physical business address
• Provide a clear unsubscribe mechanism
• Honor opt-out requests within 10 business days

Platforms handle the technical requirements. You focus on content and segmentation.

Step 5: Set your newsletter cadence and optimize subject lines

Frequency options:

Schedule	Best for	Commitment level
Weekly	High-tourism destinations with constant events	Requires dedicated content pipeline
Biweekly	Balanced approach for most markets	Manageable for small operators
Monthly	Low-maintenance baseline	Maintains presence without overwhelming subscribers

Before you hit the “Send” button, there are a few questions you need to figure out for yourself:

• How often will you send your newsletter? If you want to aim for weekly, biweekly or monthly, great! There’s no right answer. Just make sure you’re able to commit. You can adjust your schedule once you start receiving feedback too.
• What should your subject line be? That old adage applies here: Keep it simple! Refer to the three key elements of irresistible email subject lines from the experts at Copyblogger.

Step 6: Get permission

One important step to take before launching your new newsletter is to give all the people on your contact list the opportunity to opt-in to your newsletter.

This helpful chart from AWeber provides a nice overview of when it’s okay to add contacts to an email list. In short: You can only add people to your list when they’ve given you permission.

For your first message, write a brief introduction that describes:

• Who you are, with a brief description of your rental property
• Why you’re contacting them (whether it’s because they stayed with you in the past or requested information)
• Why your newsletter will benefit them (discounts, travel information, etc.)
• What your newsletter is about
• A link to your subscription page (which you will have set up using the email service)

This step may cut the number of people on your email list, but you’ll know that each subscriber is genuinely interested in what you have to offer. Plus, this is an important way to avoid the dreaded “spam” button!

By taking the time to create a newsletter list the right way, you’re likely to be rewarded with less vacancies and more visitors who are keen to stay with you over and over again.

Frequently asked questions