Caribbean Luxury Vacations

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    Save up to ¥109,000 when you book a flight and hotel together*
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Top Luxury vacation packages in Caribbean

Price found within the past 48 hours. Click for updated prices.
Grand Hyatt Baha Mar
Condado Vanderbilt Hotel
Four Seasons Resort and Residences Puerto Rico
Hotel El Convento
The Cove at Atlantis
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See all available trips from Osaka to Caribbean
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5* Luxury vacations in Caribbean

Price found within the past 48 hours. Click for updated prices.
Condado Vanderbilt Hotel
Four Seasons Resort and Residences Puerto Rico
The Cove at Atlantis
Don't see what you're looking for?
See all available trips from Tokyo to Caribbean
View all trips

4 Night Luxury vacations in Caribbean

Price found within the past 48 hours. Click for updated prices.
Grand Hyatt Baha Mar
The Cove at Atlantis
Don't see what you're looking for?
See all available trips from Osaka to Caribbean
View all trips

Top Luxury Caribbean Hotels

Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

5 out of 5
1055 Ashford Avenue San Juan
The price is ¥58,223 per night from Jul 29 to Jul 30
¥58,223
¥77,554 total
Jul 29 - Jul 30
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! (1,747 reviews)
"Housekeeping was excellent. Staff at beach was very helpful. The wind off the Atlantic kept the beach comfortable and the waves a challenge. Food was great."

Reviewed on Jul 8, 2026

Condado Vanderbilt Hotel
Bahia Principe Escape Runaway Bay - All Inclusive

Bahia Principe Escape Runaway Bay - All Inclusive

4.5 out of 5
Salt Coppers Runaway Bay Saint Ann
The price is ¥65,051 per night from Aug 2 to Aug 3
¥65,051
¥65,051 total
Aug 2 - Aug 3
includes taxes & fees
Bahia Principe Escape Runaway Bay - All Inclusive is one of the Runaway Bay sumptuous 4.5-star all-inclusive properties where you can pamper yourself with jetted ...
8.4/10 Very Good! (2,416 reviews)
"The staff was extremely helpful and curtious, they try their utmost best to ensure that we are happy and comfortable, we like that."

Reviewed on Jul 7, 2026

Bahia Principe Escape Runaway Bay - All Inclusive
Majestic Elegance Punta Cana - All Inclusive

Majestic Elegance Punta Cana - All Inclusive

4.5 out of 5
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 ...
9/10 Wonderful! (4,873 reviews)
"The resort was clean and beautiful. We truly enjoyed our stay at this resort.. Sabroso was very kind and nice. He always checked in us and ensured that we had a good time."

Reviewed on Jul 7, 2026

Majestic Elegance Punta Cana - All Inclusive
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.