Jamaica has plenty of "all-inclusive" spots where you're just a number with a wristband. Round Hill isn't one of them. Honestly, if you’re looking for a giant buffet and neon-colored slushy machines, you’re in the wrong place. Round Hill Hotel and Villas is basically a 110-acre piece of old-school Hollywood history tucked away on a peninsula near Montego Bay. It’s quiet. It’s private. And it’s a bit of a chameleon when it comes to booking.
Most people get confused about the pricing here. They search for round hill all-inclusive resorts luxury beach vacation deals expecting a standard package price, but Round Hill actually operates on a "luxury your way" model. You can book just the room, or you can add a meal plan that effectively makes it all-inclusive. It’s a subtle distinction, but it matters for your wallet.
What "All-Inclusive" Actually Looks Like Here
Let’s talk numbers. You aren't just paying for a room; you're paying for a vibe that Ralph Lauren literally designed. (Yes, he has a villa here and he styled the 36 oceanfront rooms in the Pineapple House.)
If you want the full "all-inclusive" experience, you have to opt for the Round Hill Inclusive Plan. As of 2026, this usually runs about $350 per person, per day. That’s on top of your room rate. What do you get?
🔗 Read more: City Map of Christchurch New Zealand: What Most People Get Wrong
- Breakfast, Lunch, and Dinner: Three-course meals that aren't watered down for the masses.
- Beverages by the Glass: We’re talking spirits, cocktails, wine, and beer.
- The Little Things: Daily afternoon tea in the Ralph Lauren Cocktail Lounge (very British, very chic) and a daily glass-bottom boat tour.
If that feels too heavy, they have the Modified American Plan (MAP) for around $165, which just covers breakfast and dinner. This is actually a smart move for people who want to explore Montego Bay or just grab a light snack by the pool for lunch.
The Villa Secret
If you’re traveling with a group, the villas are the way to go. They range from two to six bedrooms. Each one is privately owned, meaning the decor is unique—some are more "grandma’s Caribbean estate" and others are "modern minimalist."
But here is the real kicker: most villas come with a dedicated staff. A cook, a gardener, and a housekeeper. They will make you breakfast in your own kitchen every morning. It’s included. You wake up to the smell of Blue Mountain coffee and fresh ackee and saltfish without ever seeing another guest.
💡 You might also like: Ilum Experience Home: What Most People Get Wrong About Staying in Palermo Hollywood
Scoring Round Hill All-Inclusive Resorts Luxury Beach Vacation Deals
Timing is everything. Jamaica is expensive in the winter. No surprise there. If you want to find actual deals, you have to look at the "shoulder" seasons or specific 2026 booking windows.
- The "4th Night Free" Rule: In early 2026 (specifically stays between January 13 and April 30), Round Hill has been running a "Winter Sun" promotion. If you book four nights, the fourth is free. That’s essentially a 25% discount.
- The Summer/Fall Slump: From May 1st to mid-December, prices drop significantly. You can often find "Flash Sales" offering 35% off the best available rate. I’ve seen rates drop from $1,200 a night to around $700 during these windows.
- Kids Eat Free: For families, look for the packages that include the "Kids Stay and Eat Free" perk. Usually, this applies to kids under 12. Considering a burger at a luxury resort can run you $30, this adds up fast.
Is It Worth It?
It depends on what you value. If you want a party atmosphere, go to Sandals. If you want to feel like you’re in a 1950s Slim Aarons photograph where the staff knows your name and the beach is never crowded, this is it.
There are downsides. The beach is on the smaller side. It's a cove, not a sprawling seven-mile stretch. Also, if you don't get the meal plan, the "à la carte" prices for food will make your eyes water. A single dinner for two with drinks can easily hit $250 without trying. That’s why the round hill all-inclusive resorts luxury beach vacation deals are so vital—they cap your spending so you aren't doing math while you're trying to relax.
📖 Related: Anderson California Explained: Why This Shasta County Hub is More Than a Pit Stop
Navigating the 2026 Travel Windows
If you're planning a trip for later this year, keep an eye on the booking deadlines. Many of the best offers for the May–December 2026 window require you to book by late spring.
Pro Tip: Ask for a room in the Pineapple House if you want to be close to the pool and bar. If you want total isolation, book a Classic Villa. Just be aware that some of the higher-up villas require a bit of a hike or a golf cart ride.
Actionable Next Steps
- Audit Your Group Size: If you have more than 4 people, price out a villa versus two hotel rooms. The villa almost always wins on value because of the private staff and included breakfast.
- Check the Blackout Dates: Avoid the weeks of February 15–19 and the Easter window in late March/April. Prices peak, and deals vanish.
- Contact the Concierge Early: If you book a villa, email them your grocery list. Having a stocked fridge the moment you land is the ultimate luxury move.
- Compare the "Inclusive" Add-on: Calculate your typical daily spend. If you don't drink much alcohol, the $225 Full American Plan (no booze) is a much better deal than the $350 "Inclusive" plan.