Your browser's security settings have disabled Javascript, which is required to use this web site effectively.
Please alter your security settings. Click here to see how.

5 Tips to Retain Repeat Guests and Attract New Ones

Elizabeth Weedon | Updated 6/17/2025
5 Tips to Retain Repeat Guests and Attract New Ones

Managing a vacation rental isn’t just about one successful stay—it’s about building momentum for future bookings. A great guest experience doesn’t just encourage return visits; it also inspires glowing reviews that attract new vacationers. Here are 5 tips on how to build long-term success with both repeat and first-time guests.

1. Proactively Request Guest Reviews

Reviews can make or break a listing. Most vacationers rely heavily on guest feedback when choosing a rental—and some won’t even consider a listing without them. According to industry data, listings with multiple positive reviews see significantly more inquiries and bookings. Don’t be shy—ask your guests to share their experience, especially while their stay is still fresh in their minds.

2. Build a Personal Connection

While rental management is a business, hospitality is personal. A warm, approachable tone helps foster trust and good will. Introduce yourself in welcome materials or pre-arrival messages. If your guests feel they know and can reach you, they’re more likely to be understanding if minor issues arise—and more likely to write a kind, thoughtful review after their stay.

3. Check In Before Arrival

Reach out 5 to 10 days before your guests arrive to make sure they’re fully prepared. Remind them of important details like:

  • What to bring (e.g., linens, beach gear)
  • What’s provided (e.g., paper goods, cleaning supplies)
  • Check-in time and address
  • Access instructions

Ask if they have any last-minute questions or requests. This small gesture goes a long way in making guests feel welcomed and confident about their upcoming stay.

4. Follow Up After Arrival

Don’t go silent once guests check in. A quick message or call to ask if everything is to their liking shows that you care—and helps prevent small issues from becoming bigger problems. Many negative reviews stem from unresolved concerns that could have been addressed early with a simple check-in.

5. Reach Out After Departure

Once guests leave, return their security deposit promptly and follow up with a thank-you message. Let them know you appreciate how they left your home and remind them how much you’d value a review. While their positive experience is still fresh, ask if they’re interested in returning next season—and consider offering an incentive for booking early. (Read our 10 Tips to Acquire Positive Reviews.)

💡Final Thoughts

A little extra effort in communication and hospitality goes a long way in turning first-time guests into loyal visitors—and those loyal guests into your best marketing tool. Focus on personal touches, clear communication, and timely follow-ups to create a guest experience that’s worth repeating—and sharing.

About Elizabeth Weedon

About Elizabeth Weedon: I worked for WeNeedaVacation from 2008 until I retired in 2023. I was also one of the first vacation rental owners on the site in early 1998, when I managed my family’s Vineyard rental home. An enthusiastic member of the support staff, I provided fellow Cape and Islands vacation rental owners with advice about online marketing and rental management techniques. I created and edited much of the content on the website, as well as blogs posts and monthly newsletters. I now live on Martha’s Vineyard full time with my family.