Cabana Boys 101: What They Do and How to Book One

Somewhere between "we booked the Airbnb with the pool" and "who's making the drinks?" — that's where the cabana boy comes in.

Every pool day has the same quiet problem. Someone ends up playing bartender. Someone mans the grill. Someone takes the photos, which means she's in none of them. Usually it's the same someone, and usually she's the maid of honor.

There's a fix, and yes, he's shirtless.

What is a cabana boy, exactly?

A cabana boy is a professional party host hired for a pool day or poolside event. He serves drinks, runs the grill, leads the games and takes the photos, so the group can enjoy the day instead of running it. He is not a stripper — a cabana boy is hospitality staff with charm, typically shirtless, in swim shorts and a bow tie.

Think of him as the difference between hosting your pool party and attending it.

What a cabana boy does all afternoon

The drinks stay full — cocktails, seltzers, a suspicious amount of mimosas. The grill is handled, because nobody flew to a pool weekend to stand over burgers. The games happen — he brings them, he runs them, he hypes them. And at the end, the trash goes out and the towels get folded, which might be the most attractive thing on this entire list.

Sunscreen on the hard-to-reach spots? Handled. Politely.

No, we weren't the cabana boys on Shark Tank

People search this a lot, so — no. There was a company called Cabana Boys that pitched on Shark Tank, and it isn't us. We're The Cheeky Butlers, we've been doing this since 2022, and we've worked 500+ parties across 30+ US cities. No TV deal, just a lot of pool days.

How to book a cabana boy

You need three things: a city, a date and a rough window. Anywhere with sun works, but Scottsdale, Miami and Las Vegas are where the cabana boy earns legend status. Book 4–6 weeks out for a summer weekend; less notice is usually still fine midweek.

Planning the pool day itself rather than the staffing? We broke that down separately in the cabana boy pool party guide.

The vibe is yours to set

Every Cheeky booking runs on your spice dial. Keep it perfectly classy for the mixed crowd with mum on a lounger, or turn it up for a bride who wants a show. Pool day rolling into a big night? Add a Cheeky Dancer for the evening and make it a double feature.

The photos are real, the reviews are 5.0, and the cabana boy in the pictures is the cabana boy who shows up. No stock, no catfish.

If you're wondering what it costs or whether your date's still open, both answers are here — we're in 30+ US cities, so the pool is probably already covered.

And when you're ready, tell us your city, date, and vibe. We'll bring the bow tie.