When my business partner Bryan approached me a year ago with the idea to start what would become Island Stays Hawaii, he pointed out a gap in the market: many of his clients, after purchasing short-term rental properties, were dissatisfied with the management services available. From our first conversation, we agreed that we could do better—not just by providing better service, but by rethinking what hospitality means in the short-term rental (STR) space.
A year later, as Island Stays has grown into what I genuinely believe is one of the premier property management groups on Oahu, I’ve spent a lot of time dissecting one key question: What do guests really want? It’s the cornerstone of everything we do.
Here’s are my thoughts. I’m sure they’ll evolve as we grow, but for now, I believe that the modern guest’s wish list boils down to three key elements:
1. Invisible convenience
2. Prompt service
3. Accommodations that elicit a feeling
Let’s unpack these concepts.
Invisible Convenience: Doing More by Seeming to Do Less
Convenience isn’t a new idea in hospitality—hotels cracked this code decades ago with room service, concierges, and chocolates on the pillow. But modern travelers, especially those opting for STRs over traditional hotels, want their convenience served with a twist. They want to feel at home. That means all the perks of a high-end stay—but without the constant reminder that someone’s managing things behind the scenes.
Invisible convenience is about creating seamless experiences. Like a great referee in sports, your presence should enhance the game, not distract from it. Here’s how we achieve it:
• Stocking the Unit Thoughtfully: The essentials can’t just be “available on request.” Coffee? Already there. Beach chairs and umbrellas? Staged and ready. Sunscreen? Optional, but at your fingertips when you need it. Guests shouldn’t need to think, “Where can I get…?”—it should already be handled.
• Check-in and Check-out Systems That Don’t Suck: Instructions should be crystal clear and idiot-proof. Think digital guidebooks and how-to videos sent directly to their phones. No need to print maps or decipher blurry QR codes.
• Streamlining Recommendations: Nobody wants to hunt down a concierge or wait on hold. The best local spots—restaurants, hikes, attractions—should be in their hands as soon as they book, curated by people who actually know the area.
The goal? Empower guests to live out their adventure without us hovering nearby. We’re the concierge, housekeeper, and guide—all rolled into an invisible support system. Like Batman with less leather.
Prompt Service: The Amazon Prime of Hospitality
People hate waiting. Always have, always will. The rise of same-day delivery and instant social media dopamine has made that impatience worse, but it’s not just cultural; it’s human nature. When something goes wrong—or even when guests have a question—they want help, and they want it now.
This is tricky in STRs because we’re not hotels. We don’t have a lobby full of staff ready to sprint upstairs with extra towels. But that doesn’t mean we can’t provide lightning-fast, meaningful service. Here’s how:
1. Invest in Real, Local Teams: VAs working out of a different time zone might save money, but they can’t deliver the level of help that comes from people who know the property—and the island. Our team isn’t just trained to answer questions; they’re empowered to fix problems.
2. Don’t Over-Automate: Tech is great. Tech replacing humans? Not so much. Automation has its place (like sending guests their check-in info), but it’s not a substitute for personalized help when something actually goes wrong.
3. Prevention Beats Reaction: Most service requests come from things that should’ve been handled in advance—broken appliances, unclear instructions, missing items. We do regular quality checks to fix those proactively, which reduces the need for reactive service.
Prompt service is about being ready, not just responsive. It’s not enough to answer quickly; you have to solve quickly.
Accommodations That Elicit a Feeling
Let me paint you a picture: You’re sitting on a balcony in Medellín, watching the city lights while the Narcos theme song plays softly in the background. Or maybe you’re rinsing off your surfboard in Costa Rica, the saltwater still clinging to your skin as the sun sets behind you. These are the moments that stuck with me from my personal travels—not because of the thread count on the sheets, but because the place itself set the stage for something magical.
Hospitality isn’t about providing a bed; it’s about creating a backdrop for life’s best memories. Here’s how we aim to do that:
• Infuse Local Culture: Every unit should feel like a postcard come to life. For us, that means touches like Hawaiian art, locally made coffee, and guidebooks that reflect the island’s character—not a generic template.
• Surprise and Delight: A neon sign in the living room. A cocktail shaker by the minibar. A Bluetooth speaker ready to play a “Hawaiian Chill” playlist. These aren’t big things, but they make a big impression.
• Facilitate Connection: The best stays are the ones that bring people together. A curated board game shelf, a cozy breakfast bar for shared meals, or extras like a cocktail-making kit or a Hawaiian-themed playlist. These small touches turn a stay into an experience and create memories guests will cherish.
Eliciting a feeling is the hardest part of hospitality to quantify but the most important to master. It’s the difference between, “That was nice,” and, “I’ll never forget this trip.”
The Island Stays Commitment
At Island Stays Hawaii, our mission is simple: Create the kind of stays that guests will talk about long after they’ve left. We believe that by combining invisible convenience, prompt service, and accommodations that evoke an emotional response, we can elevate the STR experience to a new level.
We’re not just managing properties. We’re setting the stage for adventure, connection, and magic.
And to me, that’s what hospitality is all about.