Caribbean Luxury Vacations 2026

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Top Luxury vacation packages in Caribbean

Price found within the past 48 hours. Click for updated prices.

The Crane Resort

￥294,339

per person

Nov 12 - Nov 15

found 4 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Bridgetown (BGI)

8.6/10 Excellent! (1,008 reviews)

Everything and staff were excellent. Unfortunately, the local beach was disappointing.

Reviewed on Sep 16, 2026

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4 Night Luxury vacations in Caribbean

Price found within the past 48 hours. Click for updated prices.

The Crane Resort

￥294,339

per person

Nov 12 - Nov 15

found 4 hours ago

Roundtrip non-stop flight included

Tokyo (TYO) to Bridgetown (BGI)

8.6/10 Excellent! (1,008 reviews)

Everything and staff were excellent. Unfortunately, the local beach was disappointing.

Reviewed on Sep 16, 2026

Don't see what you're looking for?

See all available trips from Tokyo to Caribbean

View all trips

Top Luxury Caribbean Hotels

Condado Vanderbilt Hotel

1055 Ashford Avenue San Juan

￥47,935

￥63,850 total

Sep 20 - Sep 21

includes taxes & fees

Condado Vanderbilt Hotel is a San Juan luxury 5-star beach property where you can treat yourself to 24-hour room service, pillowtop beds, and more. Deluxe amenities ...

9.4/10 Exceptional! (1,843 reviews)

"All in all a beautiful and pleasant stay at Condado Vanderbilt Hotel! Amazing staff and the vibe was definitely lux! Will be returning back to this property someday!"

Reviewed on Sep 16, 2026

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive

Salt Coppers Runaway Bay Saint Ann

￥52,223

￥52,223 total

Sep 18 - Sep 19

includes taxes & fees

Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive is one of the Runaway Bay sumptuous 4.5-star all-inclusive properties ...

Hotel El Convento

100 Cristo St San Juan

￥47,667

￥62,348 total

Sep 28 - Sep 29

includes taxes & fees

Hotel El Convento is a San Juan luxury 4.5-star boutique property where you can pamper yourself with massage services, designer toiletries, and more. The outdoor ...

9.2/10 Wonderful! (1,000 reviews)

"The beautiful building and historic structure"

Reviewed on Sep 13, 2026

See all 88,844 properties in Caribbean

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.