How Remarketing to Your Guests Creates Lasting Loyalty
The Most Valuable Guests Are the Ones You Already Have
Every property management company invests heavily in acquiring new guests. SEO, paid ads, OTA placement, social media — the spend adds up. What many companies underinvest in is the single most profitable channel available to them: their existing guest database.
A past guest who had a good experience is the easiest booking you’ll ever close. They already know your destination. They already trust your brand. They’ve already validated their interest by spending money with you. The only question is whether you stay top of mind when they start planning their next trip.
That’s what remarketing does.
Why Remarketing Works in Hospitality
Unlike retail, where purchase cycles are short and frequent, hospitality purchases are infrequent but high-value. A family that visits your destination once a year represents thousands of dollars in annual revenue. Lose them to a competitor, and you need to spend significantly more to replace that revenue with a new guest.
Remarketing keeps the relationship alive between stays. It transforms a transactional booking into an ongoing relationship. Done well, it makes guests feel like insiders rather than customers.
The Numbers Behind Repeat Guests
- Repeat guests cost 5-7x less to acquire than new guests
- Returning guests book earlier in the season, improving occupancy forecasting
- Repeat guests tend to book longer stays and spend more on add-ons
- Direct repeat bookings carry zero OTA commissions
These aren’t marginal improvements. For a property management company with 200+ units, shifting even 10% of bookings from new OTA guests to repeat direct guests can represent six figures in additional annual profit.
What Effective Remarketing Looks Like
Remarketing isn’t sending a monthly newsletter and hoping for the best. It’s strategic, segmented, and timed to align with how guests actually make travel decisions.
Anniversary-of-Stay Campaigns
Guests who visited last February are thinking about where to go this February. A well-timed email that says “Your favorite beach house is available for the same week” converts at rates that make every other marketing channel look expensive.
Seasonal Early Access
Give past guests first access to peak season dates before they go public. This creates urgency and makes guests feel valued. It also fills your highest-revenue weeks earlier, improving your revenue forecasting.
Segmented Offers Based on Stay History
A family that booked a 4-bedroom oceanfront home is a different audience than a couple that booked a studio. SendSquared’s segmentation tools let you target offers based on past property type, length of stay, total spend, and travel dates, so every message feels relevant.
Post-Stay Engagement
The remarketing window opens the moment a guest checks out. A thank-you message, a review request, and a “plan your next trip” prompt within the first week keeps your brand fresh. Most property management companies go silent after checkout and then wonder why guests don’t come back.
Loyalty Without a Loyalty Program
You don’t need points, tiers, or plastic cards to build loyalty. In hospitality, loyalty comes from three things: consistent experiences, personal recognition, and making it easy to come back.
Remarketing delivers all three. When a returning guest receives an email that references their last stay, suggests a similar property, and offers a seamless booking link, that’s recognition. When the booking process is frictionless because you already have their details, that’s ease. When they arrive and have the same quality experience, that’s consistency.
SendSquared’s Lifetime Value tracking shows you exactly what each guest has spent over their relationship with your company. That data lets you identify your most valuable guests and treat them accordingly, before a competitor does.
Building the Engine
The property management companies with the strongest repeat booking rates share a common trait: they treat their guest database as their most important business asset. They invest in keeping it clean, segmented, and active. They automate the touchpoints that bring guests back. And they measure the results with revenue attribution that connects campaigns to bookings.
Remarketing isn’t a campaign you run once. It’s a system you build and refine. Every guest who books again validates the investment and makes the engine stronger.