Caribbean Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
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Top Luxury vacation packages in Caribbean
Price found within the past 48 hours. Click for updated prices.
Hotel El Convento
Old San Juan
Price was ￥123,840, price is now ￥115,026 per person
￥115,026
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9.2/10 Wonderful! (1,009 reviews)
An awesome experience! Thanks for the upgrade! Very charming and service oriented staff.
Reviewed on Jun 14, 2026
Condado Vanderbilt Hotel
Condado
Price was ￥145,089, price is now ￥118,508 per person
￥118,508
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9.4/10 Exceptional! (1,713 reviews)
Good hotel with no real complaints. Cigar lounge a brilliant touch, restaurant was excellent! But the hotel rooms need upgraded if they want to drive value for both clients and stake holders. Investment in property is visibly missing!
Reviewed on Jun 14, 2026
Bahia Principe Escape Runaway Bay - All Inclusive
Price was ￥611,130, price is now ￥498,776 per person
￥498,776
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.4/10 Very Good! (2,359 reviews)
Awesome customer service. Friendly staff and clean rooms. I definitely enjoyed myself.
Reviewed on Jun 17, 2026
Round Hill Hotel And Villas
Price was ￥824,565, price is now ￥713,205 per person
￥713,205
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
9.6/10 Exceptional! (292 reviews)
Fantastic resort. Villa 10 always felt like coming home and the people were wonderful. Daniel and the wonderful people who looked after us made the stay all the better. Couldn’t recommend Round Hill enough.
Reviewed on Apr 17, 2026
5* Luxury vacations in Caribbean
Price found within the past 48 hours. Click for updated prices.
Condado Vanderbilt Hotel
Condado
Price was ￥145,089, price is now ￥118,508 per person
￥118,508
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9.4/10 Exceptional! (1,713 reviews)
Good hotel with no real complaints. Cigar lounge a brilliant touch, restaurant was excellent! But the hotel rooms need upgraded if they want to drive value for both clients and stake holders. Investment in property is visibly missing!
Reviewed on Jun 14, 2026
The Ritz-Carlton, Grand Cayman
Price was ￥237,422, price is now ￥237,422 per person
￥237,422
per person
Aug 25 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to George Town (GCM)
9.6/10 Exceptional! (1,001 reviews)
One of the best resorts I have had the pleasure to visit!
Reviewed on Jun 17, 2026
3 Night Luxury vacations in Caribbean
Price found within the past 48 hours. Click for updated prices.
Hotel El Convento
Old San Juan
Price was ￥123,840, price is now ￥115,026 per person
￥115,026
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9.2/10 Wonderful! (1,009 reviews)
An awesome experience! Thanks for the upgrade! Very charming and service oriented staff.
Reviewed on Jun 14, 2026
Condado Vanderbilt Hotel
Condado
Price was ￥145,089, price is now ￥118,508 per person
￥118,508
per person
Aug 10 - Aug 13
found 1 day ago
Roundtrip flight included
New York (JFK) to San Juan (SJU)
9.4/10 Exceptional! (1,713 reviews)
Good hotel with no real complaints. Cigar lounge a brilliant touch, restaurant was excellent! But the hotel rooms need upgraded if they want to drive value for both clients and stake holders. Investment in property is visibly missing!
Reviewed on Jun 14, 2026
4 Night Luxury vacations in Caribbean
Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, Grand Cayman
Price was ￥197,304, price is now ￥197,304 per person
￥197,304
per person
Aug 26 - Aug 29
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to George Town (GCM)
9.6/10 Exceptional! (1,001 reviews)
One of the best resorts I have had the pleasure to visit!
Reviewed on Jun 17, 2026
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Condado Vanderbilt Hotel
1055 Ashford Avenue San Juan
The price is ￥59,191 per night from Jul 1 to Jul 2
￥59,191
￥78,843 total
Jul 1 - Jul 2
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! (1,726 reviews)
"Good hotel with no real complaints. Cigar lounge a brilliant touch, restaurant was excellent! But the hotel rooms need upgraded if they want to drive value for both clients and stake holders. Investment in property is visibly missing!"
Reviewed on Jun 14, 2026
Bahia Principe Escape Runaway Bay - All Inclusive
Salt Coppers Runaway Bay Saint Ann
The price is ￥60,404 per night from Jun 21 to Jun 22
￥60,404
￥60,404 total
Jun 21 - Jun 22
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! (2,384 reviews)
"Awesome customer service. Friendly staff and clean rooms. I definitely enjoyed myself."
Reviewed on Jun 17, 2026
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 ...
9/10 Wonderful! (4,845 reviews)
"The hotel do not have to many activities for the kids."
Reviewed on Jun 17, 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.
