Kay Walten

Kay Walten

🍍 Facing Booking Rejections? You're Not Alone—Here's Why

This article helps vacation rental owners secure holiday bookings by addressing common challenges and offering practical solutions.

Smart Pineapple's avatar
Smart Pineapple
Jan 23, 2025
∙ Paid

Holiday Booking Struggles?

You're Not Alone.

❌ 1st holiday inquiry: Didn’t book.
❌ 2nd holiday inquiry: Didn’t book.
❌ 3rd holiday inquiry: Didn’t book.
❌ 4rd holiday inquiry: Didn’t book.
❌ 5th holiday inquiry: Didn’t book.
...
❌100th holiday inquiry: Didn’t book.

🙌 But then, the 120th holiday inquiry, finally booked!

If you’re facing daily rejections, potential guests who ghost you, or the worst—potential guests booking your place through an OTA—you're not alone.

I’ve been there. Over the years in reservations, I've experienced it all. New Year’s often books up faster than Christmas week, and some properties still sit empty over the holidays.

If your availability calendar is looking bleak, here are a few tips to secure your holiday bookings below.

📆 Countdown to the Holiday Season

You still have time for these strategies

Flexible Booking

For the holiday season, keeping booking policies flexible can help attract more guests and ease the booking process. Here are some ideas:

  1. Deposit & Balance Paymen


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