Why Subscribe to Smart Pineapple?
Simple: We help vacation rentals, small hotels, and boutique destinations use AI to market smarter, boost direct bookings, and deliver guest experiences guests rave about while putting smaller destinations on the map. Think of us as your secret weapon for staying booked solid and still sleeping at night.
What You’ll Get
✅ Clear strategies. No jargon. Just straight talk on what works right now.
✅ Real solutions. Answers to your biggest questions:
– How do I compete with OTAs?
– How do I attract the right guests?
– How do I actually use AI in my business?
✅ Pro-level tools. Every issue delivers marketing tips, guest engagement ideas, and AI prompts built for hospitality pros who want results, not theory. Everything points toward one goal: more control, better bookings, and a stronger business.
Who’s Behind Smart Pineapple?
I’m Kay Walten, founder of Smart Pineapple and lifelong hospitality insider. Over the last 35+ years, I have been a founder, fixer, storyteller, and strategist with one goal: making travel and hospitality better for guests and the people who serve them.
I launched one of Mexico’s first online reservation services in 1996, built and sold a travel brand that thrived for nearly 30 years, and have hosted thousands of happy guests. I have taught at Temple University, trained hospitality teams worldwide, and consulted for brands from Pillsbury to Coke.
Outside the business side, I am an explorer at heart. I have stomped the jungle and explored underwater caves, climbed Kilimanjaro, sailed the Arctic, and been a member of The Explorers Club. I have volunteered in the Tanzanian bush, led hurricane relief efforts in Mexico, and even chased hot air balloons for fun.
Today, I help vacation rentals, small hotels, and destinations use AI to simplify marketing, boost direct bookings, and deliver guest experiences that stick. I have been where you are — juggling operations, guests, and growth — and I know how to turn AI from a buzzword into a business advantage.
You’re Not Alone
Most property owners feel stuck doing it all themselves. I have been there. This community is for people who want to run their business smarter, not harder.
Hospitality and tourism are evolving. You can stay reactive or you can stay ahead.
→ Join Us.
Affiliations
Proudly connected with people who get it: Vacation Rental Management Association, Vacation Rentals Professionals of Maine, Vermont Short Term Rental Alliance, and the World Travel Network.
