Surprise, Delight, and Fur Babies: The Bold Hospitality of Staypineapple with Dina Belon

How bold branding, empowered teams, and a love for dogs helped Staypineapple redefine boutique hospitality.

In this episode of The Inn Crowd, Jamie Mattingly sits down with Dina Belon, President of Staypineapple—a boutique hotel brand known for its cheeky personality, unforgettable design, and pet-obsessed culture. From their “Naked Experience” to handwritten guest notes, Staypineapple has carved out a loyal following through humor, heart, and hyper-personalization.

Dina shares how they empower team members to go off-script, why surprise and delight isn't just a marketing slogan—it’s a mindset—and how being unapologetically bold has helped the brand attract the right guests (and happily repel the wrong ones).

Whether you’re a hotelier, marketer, or just love a great guest experience, this episode is packed with ideas and insights.

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🎧 What You’ll Take Away from This Episode:

• Why being dog-obsessed isn’t just cute—it’s a growth strategy

• How Staypineapple empowers team members to create legendary surprise-and-delight moments

• Why personality-driven branding increases guest loyalty

• The power of saying, “We’re not for everyone”—and meaning it

• How Dina thinks about guest personalization beyond preferences

• Why a teabag and a box of Kleenex might be more meaningful than a comped cocktail

• What happens when your social media strategy is built by your guests

• Dina’s vision of Staypineapple as a mix of Steve Martin and Audrey Hepburn

• Ideas you can steal to make your hotel—or any brand—more memorable and magnetic

Come for the dogs, stay for the pineapple robes, and leave with a masterclass in modern hospitality.

Dina Belon Linkedin 
www.Staypineapple.com