
Caribbean Islands Luxury Vacations
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Top Luxury vacation packages in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.

JOIA Rose Hall by Iberostar - Adults Only - All Inclusive
Northern Estates
Price was ¥483,727, price is now ¥483,727 per person
¥483,727
per person
Mar 16 - Mar 21
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,004 reviews)
VIP treatment! Food was excellent!
Reviewed on Jan 1, 2026

Moon Palace Jamaica – All Inclusive
Price was ¥806,017, price is now ¥528,069 per person
¥528,069
per person
Mar 16 - Mar 21
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.2/10 Very Good! (1,845 reviews)
The hotel was mid level, the staff was acceptable & the constant pressure to sell to everyone more stays felt timeshare light. I did private excursions & hotel facilitated ones, all were fine. Food was1 star. It was limited and truly lacking. Reservations were accommodated and severe delays most nights with limited options. Poor quality- and the hotel didn’t care. Last time doing all inclusive.
Reviewed on Jan 3, 2026

Jamaica Inn
Price was ¥652,952, price is now ¥533,341 per person
¥533,341
per person
Mar 2 - Mar 7
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Montego Bay (MBJ)
9.6/10 Exceptional! (447 reviews)
It was amazing, the room service, the view, the staff, the beach. We will definitely be regulars. This was a birthday trip to remember!
Reviewed on Nov 1, 2025

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View all trips5* Luxury vacations in Caribbean Islands
Price found within the past 48 hours. Click for updated prices.

JOIA Rose Hall by Iberostar - Adults Only - All Inclusive
Northern Estates
Price was ¥483,727, price is now ¥483,727 per person
¥483,727
per person
Mar 16 - Mar 21
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
9.2/10 Wonderful! (1,004 reviews)
VIP treatment! Food was excellent!
Reviewed on Jan 1, 2026

Moon Palace Jamaica – All Inclusive
Price was ¥806,017, price is now ¥528,069 per person
¥528,069
per person
Mar 16 - Mar 21
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.2/10 Very Good! (1,845 reviews)
The hotel was mid level, the staff was acceptable & the constant pressure to sell to everyone more stays felt timeshare light. I did private excursions & hotel facilitated ones, all were fine. Food was1 star. It was limited and truly lacking. Reservations were accommodated and severe delays most nights with limited options. Poor quality- and the hotel didn’t care. Last time doing all inclusive.
Reviewed on Jan 3, 2026
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See all available trips from Tokyo to Caribbean Islands
View all tripsTop Luxury Caribbean Islands Hotels

Condado Vanderbilt Hotel
1055 Ashford Avenue San Juan
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 ...
9.2/10 Wonderful! (1,665 reviews)
Beautiful hotel, great staff, lives up to its reputation.
Reviewed on Dec 29, 2025

Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive
Salt Coppers Runaway Bay Saint Ann
Bahia Principe Luxury Runaway Bay - Adults Only - All Inclusive is one of the Runaway Bay sumptuous 4.5-star all-inclusive properties where you can pamper yourself ...
8.2/10 Very Good! (2,482 reviews)
Great place
Reviewed on Dec 10, 2025

Majestic Elegance Punta Cana - All Inclusive
Playa Bavaro - Punta Cana Punta Cana La Altagracia
Majestic Elegance Punta Cana - All Inclusive is one of the Punta Cana lavish 4.5-star all-inclusive properties where you can treat yourself to jetted bathtubs ...
8.8/10 Excellent! (4,611 reviews)
Friendly, helpful staff, great food and drinks, impeccably clean rooms, pool and beachfront.
Reviewed on Jan 2, 2026
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
