Most Expensive Caribbean Island Resort | Passport Kings Countdown | Passport Kings

Most Expensive Caribbean Island Resort | Passport Kings Countdown

Passport Kings is supported by you.
When you buy through links on our site, we may earn an affiliate commission. Learn More
I never recommend anything I haven't tried myself”

The reason why I came up with this countdown called "The most expensive Caribbean Island Resorts" is because I made a countdown video recently about the cheapest Caribbean Resorts

and guess what?

No one cared and the views were abysmal.


People, who travel are usually not broke!

You either got to the bag in just a few hours using your hustling skills - or you saved your money up from work and now you’re ready for an Island Adventure that will put other people’s social media travel pictures to shame.

Well, you’re in the right place!

I’ve been traveling to the Caribbean for over 10 years now.

I’m going to show you the Most Expensive Caribbean Island Resorts to binge a small fortune on.

My number 5 pick will probably be the most surprising if you’ve been following current Caribbean news.

10. Turks and Caicos

If you have $2400 per night to spend on a Caribbean resort, don’t look any further than Ambergris Cay.

This resort is on a private island South of the Turks and Caicos mainland called Big Ambergris Cay. The back and forth private airplane transports are included within the hefty price.

It's 5 stars and has received almost all "Exceptional Class" ratings from its recent customers with the cleanliness of the resort being their most praised response.

When you wake up every morning, the Ocean will be right at your front door and out of every window.

The family-friendly, all-inclusive resort has strong wifi, pools 24-hour room service, and is surrounded by white sands. It has 2 world-renowned restaurants.

The entire island is taking social distancing and sterilization seriously with contactless check-in surface cleanings and temperature checks.

This is not for people on a tight budget. Just because you know the value of your money does not mean you aren't aware of the value your money can bring.

Every dime spent in this highly exclusive resort in Turks and Caicos will be well worth it. 

View deals on Tripadvisor

9. Barbados

Around my Birthday, July 23-30 EVERYTHING in Barbados is sold out.

That is because the CropOver Festival in Bridgetown Barbados takes place the last week of July.

But even when going to Barbados any other time of the year, (We at Passport Kings always recommends July-November) you will get white sand beaches and friendly culture. It’s easy to see why Barbados is one of the most popular tourist destinations in the Caribbean.

At roughly $1323per night, and waiting until September, you can enjoy Sandals Royal Barbados.

This couples-only hotel will give you a sea view, and an All-inclusive room in the entertainment district on the beach. Here you will be within an 8-minute walk to Turtle and Dover Beach.

The scenery is the stuff that vacation Dreams are made of. This is a newer resort, just completed in 2017.

The price tag is hefty but if you want to live like the Rich for at least a week, this is the place to do it.

The Passport King Visits Jamaica

8. Jamaica

Sandals in Jamaica is famous for its all-inclusive vacation packages. Jamaica's Sandals has won multiple awards for its excellent service. Sandals Montego is considered the BEST that Sandals has to offer on an island in the Caribbean.

But Guess what?

When it comes to Jamaica, 1 of the most expensive and well worth the money resorts in Jamaica is the Adults only, All-Inclusive Beach Villas at Excellence Oyster Bay

How Much is it? Right now it is 40% off making it $2566per night. The Normal price is $4,204

But trust me, the adventure you will have and the pictures full of memories that you will take will be some of the most lit when compared to anyone else's pictures of their Jamaican Vacation.

You will be in Foulmoth which is one of the cities just east of Montego Bay. You may recognize the area because many cruise ships dock here when making a stop in Jamaica.

It is also within 3 miles of Blue Waters Beach Club, Burwood Beach, and Luminous Lagoon. Silver Sands Public Beach and Greenwood Great House are also within 12 miles of this resort.

7. St. Lucia

While St. Lucia may be known as the Caribbean island of romance, it’s also known as one of the most expensive destinations on the planet.

Jade Mountain Resort hovers around $2358 per night.

With that price, you will get whirlpool tubs and Oceanfront rooms. The best part of being oceanfront is this is the prime space to see the world-famous St. Lucia Pitons right outside of your window.

Everywhere you turn there will be a walkway bridge to another private infinity pool.

Saint Lucia is no ordinary Caribbean island. The mountains, jungles, beaches, and famous landmarks of the Pitons (two volcanic plugs on the southwestern coast of the island) whisper echoes of the history to all who visit.

The island itself is a biodiversity hotspot, offering four different ecozones that span from tropical rainforest to mangrove swamps.

Plane shot of Caribbean Islands

6. Antigua and Barbuda

The most expensive resort out in Antigua is Jumby Bay Resort.

The Beachside Suites will run you about 3,100 per night.

The breathtakingly beautiful islands have some of the planet’s most ethereal turquoise seas and the finest powdery-sand beaches are 1 of a kind.

The main attraction, which is only a few steps away, is Dickenson Bay which is a long strip of beachfront filled with cafes, bars, and watersports concessions.

It is also home to a 1-mile long coral reef.

You will be on what is called "Long Island" (AKA Jumby Bay) which is the 5th largest of the Barbuda and Antigua Islands.

Spending this much per night, you may not want to stray too far away from your luxurious suite where the staff is eager to cater to your every need and desire.

5. St. Barts

In 2008, Forbes ranked St. Barts number 11 on its list of The World’s Richest Places by GDP Per Capita.

This French island off of Guadeloupe is known for its posh real estate and high-end restaurants.

When you are ready to break the bank, you need to stay in the Quartier Lorient. Once you're there Get the Villa in the resort called La Sereno.

This deal will run you around $5600 per night. so for 7 nights, you will be paying $40 Thousand Dollars

The service is unmatchable. The staff will know how much you are spending and they will treat you that way while staying on this private beach.

You will be near Grand Cul de Sac and Marigot Beach.

The entire place was just renovated in 2019. They had convenience, contemporary, and the desires of people who live baller status in mind while rebuilding.

Oceans of Bermuda

4. Bermuda

The Residences at The St. Regis Bermuda will cost you $4500 per night for the Penthouse which features 3 bedrooms that are all Balcony and Ocean Front.

The Residences at St. Regis is ranked as Bermuda’s finest hotel by every traveler whose ever been here.

With a luxury spa and private beach, as well as a luxurious setting with traditional Bermudian architecture, you can expect high-quality service from its guests.

Attractions in the immediate area include Somers Garden, Bermuda Aquarium Museum and Zoo (BAMZ) for short, and Bermuda Underwater Exploration Institute and Front Street.

Long gone are the days of worrying about the Bermuda Triangle.

While in this St. George resort, you will not have a worry in the world.

Expenses Considered
Flight Back and Forth Cost of Resorts Cost of Activities
Caribbean flights are usually low Some Resorts have deals Excursions found everywhere
The USA has lots of flights leaving Some resorts stick to their prices Waterhorse riding, Jet Skying.

3. The Cayman Islands

Grand Cayman is an expensive but worthwhile destination for travelers seeking first-class service, a thriving cruise port, and a broad selection of upscale amenities.

When budget is not your main concern, you will get the chance to experience Grand Cayman the way it was meant to be experienced, from the Caribbean Club Luxury Condo Hotel.

Right in the middle of the 7 Mile Beach, you will experience high-end rooms in a boutique hotel.

You will always have an area to yourself while on the beach because this hotel's secluded area of the beach is never overcrowded.

The price tag is not even that bad when compared to the others on this list coming in at $1680 per night. While in Grand Cayman it is highly suggested that you rent a private charter to see stingrays and go snorkeling.

2. The British Virgin Islands

While in The British Virgin Islands, the things to do are visit White Bay, The Baths or charter, and Dream Yacht

Rates start at $2,995 a night, so it’s no surprise that Necker Island was going to be 1 of the most expensive Caribbean resorts.

Necker Island, a 74-acre private island is owned by Virgin founder Richard Branson and frequented by celebrities such as Bill Gates and David Bowie.

Guests can either stay in luxury villas or on one of three floating villas offshore.

Yes, there’s WiFi...if you can get a signal over those crystal clear waters!

Highway in Puerto Rico

1. Puerto Rico

Rich history and culture, exceptional food, pristine beaches, majestic mountains, relaxation, adventure – all packed into one sun-kissed Caribbean paradise. La Isla del Encanto is full of people who are Buena Gente (which is boricua slang for the kind and friendly) and welcoming. 

Dorado Beach is the upper-class Resort here, which is a Ritz Carlton Reserve.

If you want to stay in the 1 Bedroom Rooftop Balcony Suite, where you will get a breathtaking view of the West Beach, you will have to fork over $4,899 per night.

The Suite sleeps 4 and you will get 1700 sp feet.

I do not see you leaving your room that much but if you do, around every corner of this sun-washed medley of Spanish and American influences, you’ll find a celebration of life, a vibrant cultural experience, mouthwatering food for the soul, and a captivating rhythm.

If you are from NYC, for some reason, you will feel like you're home.

Tourists from around the world are flocking to Puerto Rico for its charming colonial towns, white-sand beaches, and year-round tropical climate.

Because Puerto Rico is an American territory, most travelers can easily take advantage of US customs and immigration regulations (the same as if they were vacationing stateside).

Not needing a Passport can come in handy if you're traveling with a group that does not travel as much as you do.

Puerto Rico is a great way for them to enjoy authentic Caribbean vacation travel. Of course, you can find much cheaper hotels than Dorado in Puerto Rico just like you can find much cheaper rooms in every Caribbean Island that I've mentioned.

But hey, you only live once.

Beach Umbrella in Caribbean Sea


Any of these resorts will cost a small fortune but after spending it, you will be fully aware of the full magnitude of the Caribbean.

For those who want the best of the best when it comes to luxurious, pampered vacations, these Caribbean offers will get you into some of the best experiences in the world for your money.

Budget travel certainly has its place! Especially if you haven't been anywhere for a while and you need to unwind really quick.

But sometimes it's only right to withdraw a big chunk of savings or investment loot and treat yourself like a king...



Leave a comment

My name is Roklan. I'm a travel advisor. I make Passport Kings Travel Videos to inform, preview and excite you about Vacation Destinations and other travel-related information. Discover, Preview and Book Travel with Passport Kings

Get my Make money online to Travel More Cheat Sheet