Caribbean Luxury Vacations

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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

Grand Hyatt Baha Mar

¥330,136
per person
Oct 25 - Oct 29
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Nassau (NAS)
8.8/10 Excellent! (5,351 reviews)
The Cove at Atlantis

The Cove at Atlantis

¥421,186
per person
Oct 25 - Oct 29
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Nassau (NAS)
8.6/10 Excellent! (1,008 reviews)
The Crane Resort

The Crane Resort

¥368,135
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Bridgetown (BGI)
8.6/10 Excellent! (1,011 reviews)
Friendly, helpful staff and regular communication via email.

Reviewed on Aug 21, 2026

Colony Club, a Luxury Collection Resort, Barbados

Colony Club, a Luxury Collection Resort, Barbados

¥504,392
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Bridgetown (BGI)
8.8/10 Excellent! (448 reviews)
Room is very clean . Great location with beautiful beach . Best hotel in Barbados .

Reviewed on Aug 20, 2026

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5* Luxury vacations in Caribbean

Price found within the past 48 hours. Click for updated prices.
The Cove at Atlantis

The Cove at Atlantis

¥421,186
per person
Oct 25 - Oct 29
found 21 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Nassau (NAS)
8.6/10 Excellent! (1,008 reviews)
Colony Club, a Luxury Collection Resort, Barbados

Colony Club, a Luxury Collection Resort, Barbados

¥504,392
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Bridgetown (BGI)
8.8/10 Excellent! (448 reviews)
Room is very clean . Great location with beautiful beach . Best hotel in Barbados .

Reviewed on Aug 20, 2026

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.
The Crane Resort

The Crane Resort

¥368,135
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Bridgetown (BGI)
8.6/10 Excellent! (1,011 reviews)
Friendly, helpful staff and regular communication via email.

Reviewed on Aug 21, 2026

Colony Club, a Luxury Collection Resort, Barbados

Colony Club, a Luxury Collection Resort, Barbados

¥504,392
per person
Nov 12 - Nov 15
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Bridgetown (BGI)
8.8/10 Excellent! (448 reviews)
Room is very clean . Great location with beautiful beach . Best hotel in Barbados .

Reviewed on Aug 20, 2026

Don't see what you're looking for?
See all available trips from Osaka to Caribbean
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Top Luxury Caribbean Hotels

Condado Vanderbilt Hotel

Condado Vanderbilt Hotel

1055 Ashford Avenue San Juan
¥47,526
¥63,305 total
Aug 30 - Aug 31
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! (1,859 reviews)
"Room was cleaned the first three days and fully stocked on complimentary chocolate bars & chips however the other two days they did not come in the do much and we had to ask front desk for replenishment and extra because we were a family of 3. The views are amazing, staff was super helpful & friendly ..."

Reviewed on Aug 22, 2026

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

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

Salt Coppers Runaway Bay Saint Ann
¥48,178
¥48,178 total
Sep 21 - Sep 22
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 ...
Bahia Principe Escape Runaway Bay - Hyatt Inclusive Collection - Adults Only - All Inclusive
Majestic Elegance Punta Cana - All Inclusive

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! (4,962 reviews)
"The staff at this resort were absolutely AMAZING!!! Peppa is the best entertainment person I’ve ever met, Ramon was a fantastic server, Ismael at the club swim up bar was friendly, his singing & dancing were awesome, Nathan was the best butler you could ask for. Everyone greets you and smiles, the ..."

Reviewed on Aug 22, 2026

Get rates
Majestic Elegance Punta Cana - All Inclusive
See all 86,636 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.