Independent hotels and vacation rentals should run a 10-minute AI audit to see how tools like ChatGPT, Google summaries, and OTAs are publicly describing their property without their input. When AI-generated descriptions don’t match reality, expectation gaps erode reviews, ratings, and direct bookings, making proactive source updates a critical part of modern hospitality marketing.
Latest blog posts

Culture isn’t a marketing theme; it’s a business advantage. This post shows how small hotels and vacation rentals can turn authentic local stories, artisan partnerships, and responsible use of AI into sustainable guest experiences that drive bookings and preserve community value.

Stop marketing alone. Learn how small destinations and hospitality operators can turn local alliances into big impact—with data-backed strategies, simple partnership steps.

Great hospitality isn’t just service — it’s strategy. This post unpacks how every guest interaction can become free marketing for your property. You’ll learn how to design share-worthy moments, encourage guests to tell your story, and use their feedback to raise rates and bookings

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.

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.




