Caribbean Vacations & Trips from ￥358,869

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Top destinations in Caribbean

Bayahibe Beach featuring general coastal views
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Punta Cana

Punta Cana

The Latest Caribbean Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Ocean Coral Spring - All Inclusive

Ocean Coral Spring - All Inclusive

5 out of 5
Price was ￥453,820, price is now ￥358,869 per person
￥358,869
per person
Mar 14 - Mar 17
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.4/10 Very Good! (3,949 reviews)
Great staff everyone was lovely, food was good too the oxtail tacos were amazing. There is a lot to do there and shows every night. Would return to visit again

Reviewed on Jan 7, 2026

Hotel Riu Palace Aquarelle - All Inclusive

Hotel Riu Palace Aquarelle - All Inclusive

4 out of 5
Price was ￥532,058, price is now ￥373,086 per person
￥373,086
per person
Mar 14 - Mar 17
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.8/10 Excellent! (2,062 reviews)
Beautiful room, friendly and accommodating staff, excellent entertainment and team and great food.

Reviewed on Jan 7, 2026

Hotel Riu Reggae - Adults Only - All Inclusive

Hotel Riu Reggae - Adults Only - All Inclusive

4 out of 5
Price was ￥515,278, price is now ￥388,435 per person
￥388,435
per person
Mar 14 - Mar 17
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.6/10 Excellent! (2,018 reviews)
Rooms were great, very clean. The food and entertainment were good.

Reviewed on Jan 10, 2026

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

5 out of 5
Price was ￥516,378, price is now ￥406,016 per person
￥406,016
per person
Mar 14 - Mar 17
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.6/10 Excellent! (119 reviews)
We stayed post Melissa and they were working very hard to on repairs. The Signature side was being worked on as it was hit the hardest so we were placed in a third floor ocean view room. All the restaurants were open and events were taking place at various times. We happened to be there for their champagne tree lighting ceremony and it was beautiful. We have stayed at this resort a few times now and always love it. The staff are always super friendly and accommodating. We will likely return in the future.

Reviewed on Dec 24, 2025

Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
Price was ￥454,333, price is now ￥359,122 per person
￥359,122
per person
Mar 14 - Mar 17
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.4/10 Very Good! (3,680 reviews)
Amazing room, excellent service, friendly people. This is a must-repeat trip and stay for me.

Reviewed on Jan 10, 2026

Caribbean Hotel Deals

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St San Juan
Fully refundableReserve now, pay when you stay
9/10 Wonderful! (1,004 reviews)
the place is beautiful. the pool is nice. but like many other restaurant in puerto rico. its breakfast slow

Reviewed on Jan 8, 2026

Get rates
Hotel El Convento
British Colonial - Nassau

British Colonial - Nassau

4 out of 5
Number One Bay St Nassau
Fully refundableReserve now, pay when you stay
The price is ￥41,953 per night from Jan 11 to Jan 12
￥41,953
￥60,677 total
Jan 11 - Jan 12
includes taxes & fees
8.6/10 Excellent! (2,146 reviews)
The room was spotless and the staff was so nice

Reviewed on Jan 6, 2026

British Colonial - Nassau
Hotel Rumbao, a Tribute Portfolio Hotel

Hotel Rumbao, a Tribute Portfolio Hotel

4 out of 5
100 Brumbaugh Street San Juan Puerto Rico
The price is ￥33,417 per night from Jan 26 to Jan 27
￥33,417
￥43,055 total
Jan 26 - Jan 27
includes taxes & fees
9/10 Wonderful! (1,455 reviews)
This was a great place to stay the only negative is the pool area the outdoor furniture needs updating, and some days the housekeepers didn’t show up but other than that it was a great room and excellent location

Reviewed on Jan 9, 2026

Hotel Rumbao, a Tribute Portfolio Hotel
See all 84,461 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.

Frequently asked questions

Can I travel to Caribbean right now?
For all the up-to-date facts about visiting Caribbean, take a look at our Covid-19 Travel Advisor. From quarantine policies to travel restrictions and more, Expedia will help make your trip planning as stress-free as possible.
If I'm not able to travel, can I cancel my Caribbean vacation package?
Your situation can change suddenly, so yes, you can. You may be able to change or cancel your Caribbean vacation package for free if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel and rebook, but your car rental company, hotel or airline may charge a fee. Looking for more information? Look up our Customer Service Portal. We'll help make sure your trip goes off without a hitch.
When is the best time of year to visit Caribbean?
There's a real advantage to taking your Caribbean vacation in . You can usually pick up the best deals at this time. , on the other hand, is the most expensive time to visit. If you like the buzz of peak season, head to Caribbean in . The calmer months of will help you avoid the crowds.
How far in advance should I book my Caribbean vacation?
It all depends on the air carrier, but you can usually look up international airfares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky travelers will occasionally find a cheaper ticket only weeks before the date of departure.
What should I know before booking a Caribbean travel package?
So many places to go, so many things to see and do. With a travel package, you'll be able to afford more of them. Bundle your hotels, rental cars and flights and make big savings.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.