Hospitality Grows Here

Rethink Hospitality + Tourism Marketing with Strategy + Soul

We help vacation rentals, boutique hotels, property managers, and destinations grow with clarity, creativity, and practical AI strategies.

So your brand stands apart—drawing the right guests in with loyalty-led marketing that works.

Trusted by Clients. Aligned with Industry Leaders.

From Promise to Practice

Good hospitality is never off the shelf. Neither is the way we work with you.

Like Good Hospitality, It Lasts

You’re building more than bookings—you’re building trust. Let’s make it last.

Smart Pineapple
Booked Once. Remembered Always
Real results

You create the moment. We make sure it echoes.

Expert strategies
More Than a Playbook—It’s a Partnership

You deserve a partner who understands how you work—not just what you do.

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What We Do
No Templates
Just Strategy That Fits You

From mountain lodges to coastal towns, we tailor strategy to how you actually operate.

Guest Experience
& Positioning

Bring back past guests. Attract new ones. We help you speak to both—clearly and creatively.

Digital Marketing
Stratgies

From voice to visibility, we build strategy that works—for your brand, your bookings, and your team.

Modern Tools
Human Hospitality

We apply AI where it works—so you can focus on what matters most: connection.

Why Smart Pineapple

Rooted in Experience. Focused on What Matters.

Smart Pineapple was founded by Kay Walten—a hospitality and tourism marketing expert who's been in your shoes since 1996.

We’re hospitality people—not tech bros. We know what it’s like to juggle bookings, exceed expectations, and still breathe. We help you grow with clarity, warmth, and strategy that works.

Clarity Builds Trust.

Straight talk. No sugarcoating. Happy clients, happy guests.

Grow What Lasts.

Smart Innovation. Long-Term Partnerships. No Hype.

Reach the Right People

Real Strategies.
Real Results.

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Backed by us.
Built Around You.

Work with real people, not pre-set plans. Strategy, tools, and support shaped by how your business actually runs.

Smart Pineapple Destination Marketing
Consulting & Projects
Smart Pineapple Vacation Rental Marketing

That's right, hospitality and tourism never sit still. We help you realign your strategy, focus on what matters now, and move forward with clarity.

Smart Pineapple AI for Hospitality
Ways To Work Together
Support That Fits

Not everyone needs the same level of support. Done-with-you or done-for-you, we tailor the experience to fit your goals—no runaround, no one-size-fits-all.

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Strategy

For the Hosts Who Give a Damn.

We do too. Let’s skip the fluff—just a focused chat to get you unstuck and moving.

Don’t believe us? People talk

Our reputation speaks for itself - just listen to what people are saying about us!
“Patient. Passionate. Humble. Direct. That’s Kay. She’s not trying to impress you. She’s trying to help. And it shows."
5 of 5 Stars
“Smart Pineapple bring ease to your day.  Insightful especially in today’s ‘new marketing’ world of Social Media, algorithms, booking platforms, blogs, and the list goes on."
5 of 5 Stars
Lousensia Parr
Director of Marketing, Lanzerac Hotel, Cape Town
"If you’re in the STR space and want to stay ahead of the curve, follow what Kay is building. She’s the real deal."
5 of 5 Stars
Sai Chandrasekharan
Dream Vacay Escapes, Myrtle Beach, NC
"In today's world of content, an endless need of content, it is very hard to individuals and keep up. If you are doing marketing alone, I think Smart Pineapple is a great solution!"
5 of 5 Stars
Marianne V.
Vacation Marketing Consultant, Boulder Colorado
"Smart Pineapple - Top 10 Smart Hospitality Solution Companies 2024"
5 of 5 Stars
Travel & Hospitality Tech Outlook
April 2024
FAQ

If hospitality and tourism are your core, we’re your people.

These are some of the questions we get asked by our clients, partners, and community.

What types of businesses do you work with?

Vacation rentals, boutique hotels, property managers, destinations, and tourism brands. We work best with businesses that live and breathe hospitality and tourism.

Do I need to know anything about AI before working with you?

Not at all. We meet you where you are. Whether you’re just curious or already experimenting, we’ll make it practical and understandable.

Can you help with social media, email, or my website?

Yes. From content and campaigns to email flows, booking funnels, and website optimization—we help you create a guest experience that connects.

Do you offer one-time services or ongoing support?

Both. Some clients bring us in for a reset or a special project. Others work with us long-term for consistent support.

How many clients do you take on?

Only a few each year—so we can stay hands-on, collaborative, and clear.

Thoughtful strategy for brands that want meaning—not just marketing.

What You Can Expect From Us

Built on Experience

Not just studied. Lived. With 35+ years in hospitality, tourism, and marketing.

Strategy Meets Soul

We blend content, guest experience, and real marketing that works.

Built on Relationships

You’re not just a client. You’re part of the story—with your guests, not just above them.

Let's See If We're A Fit

We work with a handful of clients each year—because thoughtful work takes focus.

We’d Love to Hear from You.

Don’t be shy—whether you're just exploring or ready to dive in, we're all ears.

Say Hello

We’re a small, friendly team—drop us a line and say hello.

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Updates

Best solution in a place where you can get your all problem solution to.

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More
Prompts for Hospitality + Tourism

In 2025, short-term rental laws are tightening and fast. This blog shows you how to use AI tools like ChatGPT, Gemini, or Perplexity to instantly check STR regulations for your location.

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Updates

Still hoping the right guests just find you? Hotels don’t leave it to chance—and neither should you. This guide shows how guest personas help you attract, host, and price with actual intention (and fewer headaches).

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Updates

What do Smart Pineapple and Taylor Swift have in common? A focus on ownership, loyalty, and standing out—without big budgets or big egos.

Real People.
Real Hospitality.
Lourensia Parr
Lanzerac Hotel, Cape Town - Client
Brian Montgomery
The Killington Group, Vermont - Client
Laura Bush
Hotel Akumal Caribe, MX - Hospitality Pro
Marcy Essy
House of the Sun Akumal, MX - Client
Marianne Volkmer
Vacation Rental Pro - Community
Steve Wyman
New England Outdoors - Client
Ready to Create Something Guests Will Remember?

Let's shape a story worth staying for.