Travelers don’t choose OTAs because they love them. They choose them because, under pressure, predictability feels safer—and trust is formed earlier than most hospitality brands realize.
Latest blog posts
Travelers don’t book bedrooms — they book belonging. Learn how storytelling beats amenities, boosts bookings, and turns your property into a memory guests can’t stop sharing. It includes a ready-to-use AI prompt to uncover your property’s hidden stories, a 10-minute story audit challenge
Expanding your property without proven demand is a costly gamble. This playbook flips the script: analyze guest reviews, build one irresistible upsell, track KPIs, and only expand when the numbers force your hand. With real case studies, you’ll see how operators generate thousands in revenue by monetizing what guests already love. Includes a free Smart Pineapple KPI & Offer Tracker to test the system in under two minutes.
Big brands chase scale. Small operators win with heart. This guide shows how to turn your size into an advantage with personal touches, smart tests, and local partners.
Travelers scroll through more than 141 pages of content before they ever click “book.” If your property isn’t showing up with consistent emails, guest stories, and social proof, you’ll stay invisible while your competitors cash in.
Discounts fill rooms, not hearts. Slash rates and you’ll get deal-chasers who vanish tomorrow. Add value, recognition, and story—and guests will rebook before they check out.
Vrbo has rolled out a strict new host cancellation policy that could cost vacation rental owners thousands. This post breaks down the rules, penalties, and communication requirements, then offers the Vrbo Survival Stack—a ladder of strategies from Basic to Bulletproof—to help hosts protect revenue, avoid fines, and thrive in 2025.
Marketing shouldn’t feel like juggling flaming torches. Copy this one AI prompt, get a week’s plan in minutes, and save your late nights for margaritas instead of Canva.
Airbnb’s Reserve Now, Pay Later drives bookings for them but creates cancellations and lost cash flow for you. Smart hosts use stricter rules, upfront payments, and AI tools to turn RNPL chaos into profit.
Big hotels automate guests into chaos. Smaller properties earn loyalty with people who answer, tech that works, and stays worth bragging about.
Taxes in Canada just got personal for Airbnb hosts. From licensing rules to surprise GST, this guide breaks it down before the CRA breaks you.
Trying to find the Smart Pineapple platform? You’re not wrong—we just outgrew it. Turns out, AI alone doesn’t cut it when what you really need is strategy, support, and someone who speaks fluent hospitality and tourism.
