Over the last three years, I’ve stayed with my family at The Landings in St. Lucia, Calabash in Grenada, and Carlisle Bay in Antigua.

They often get lumped into the same general “luxury Caribbean resort” category, but having actually stayed at all three, I think they offer very different experiences. I thought it might be helpful to compare them from a family perspective.

For transparency, I’m a travel advisor, but these were personal family trips and I paid for all three stays. Some were booked at discounted industry rates, but none were hosted.

My boys were also at different ages on each trip: roughly 2½ and 8 at The Landings, 3½ and 9 at Calabash, and 4 and 10 at Carlisle Bay. So I’ve experienced these properties with both a very young child and an older one.

If a friend asked me which one to book, I actually wouldn’t start with “Which is the best hotel?”

I’d ask: How important is the beach? How much space do you need? Do you want a small boutique hotel or a larger resort? How much do you care about design and updated rooms? And what does “luxury” mean to you?

Here’s how I’d break them down.

The Landings, St. Lucia

Of the three, this is the one I’d look at first for a family that wants space, a great beach and good value for the amount of room you’re getting.

We had a true two-bedroom residence with a living room, kitchen and dining area. It really felt like having an apartment in the Caribbean rather than trying to fit a family into a traditional hotel room.

And of these three resorts, The Landings gets my vote for the best beach.

The property itself is quite large. Depending on where your unit is located, you may find yourself using golf carts to get around. Personally, I’d opt for one of the beachfront units if the budget allows.

One important thing to know is that the residences aren’t all identical. There are timeshare units within the property, and décor and condition can vary. That makes the exact unit you book more important here than it might be at a traditional hotel.

I wouldn’t put The Landings in quite the same luxury category as Calabash. To me, it feels more like an upscale Caribbean resort than a true luxury boutique hotel.

But that’s not necessarily a negative.

If I were traveling with young children and wanted two bedrooms, a kitchen, a living room, a fantastic beach and plenty of space, The Landings could easily make more sense than spending significantly more for a higher-end boutique property.

I’d choose The Landings for: families with younger kids, anyone who needs a lot of space, and people who put a beautiful beach high on their priority list.

Calabash, Grenada

This is the one I would personally go back to in a heartbeat.

It’s the smallest of the three, and to me it felt the most genuinely luxurious. Not because it was flashy, but because everything felt personal.

The resort is only about 15 minutes from the airport, which is wonderful after a flight with kids.

The staff got to know our boys. One evening we had cocktails with the owners of the hotel. There was this feeling that you were being welcomed into someone’s home rather than simply staying at a resort.

And the food was outstanding. Not just “good for a Caribbean resort.” It was some of the most memorable food I’ve had anywhere.

The beach experience was also completely different from staying at a large resort. At any given point, there might have been seven people on the beach.

There were times when it honestly felt like we had our own little private island.

The trade-off is space and price. Our accommodations at Calabash were smaller than what we had at The Landings, and Calabash is the more expensive experience.

But if all three properties cost exactly the same tomorrow, this is the one I’d choose for my own family.

I’d choose Calabash for: travelers who value exceptional food, personal service, intimacy and a true boutique luxury experience more than having the largest room or the biggest resort.

Carlisle Bay, Antigua

Carlisle Bay is probably the most nuanced of the three for me.

The setting is beautiful and we had some genuinely memorable experiences there. We also had the resident cats who became extremely interested in our food, which my children found much more entertaining than I did. 😂

But this is an older property, and I think that’s important to know when comparing it with other Caribbean resorts at this price point.

Some of the common areas felt quite dated to me and were in need of renovation when we stayed.

However, there’s a big exception: the new adults-only beachfront suites are gorgeous.

Those feel like a completely different experience.

If I were planning a romantic Caribbean trip as a couple and could book one of those new beachfront suites, Carlisle Bay would absolutely be on my list.

That’s also why I’d pay close attention to room category here. Your impression of Carlisle Bay could be quite different depending on exactly where you’re staying.

I’d choose Carlisle Bay for: a couple looking for a romantic Antigua stay, particularly if they can book one of the beautiful new beachfront suites.

So which would I choose?

Best for a young family wanting space/value: The Landings
Best beach: The Landings
Best overall luxury experience: Calabash
Best food: Calabash
Best intimate/boutique feeling: Calabash
Best for a romantic stay in a brand-new beachfront suite: Carlisle Bay
The one I’d personally return to tomorrow: Calabash

For me, this is why questions like “What’s the best luxury family resort in the Caribbean?” are so difficult to answer without knowing the family.

The Landings gave us substantially more space and my favorite beach of the three.

Calabash gave us the most personal service, best food and strongest overall luxury experience.

Carlisle Bay has a gorgeous setting and those beautiful new beachfront suites, but some of the older parts of the property felt dated when we visited.

Three good hotels, but I’d recommend them to three very different travelers.

Happy to answer questions about any of them, especially if you’re trying to decide between these or similar Caribbean properties. I’ve stayed at all three with my own kids, so I’m happy to get specific about rooms, beaches, food or the family experience.