Caribbean Vacations & Trips from ￥235,513

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Top destinations in Caribbean

Dominican Republic which includes a sunset and general coastal views
FlightsFlightsHotelsHotels

Santo Domingo

Santo Domingo

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
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.2/10 Very Good! (3,566 reviews)
The staff was kind and the food was good

Reviewed on Jul 8, 2025

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

The Signature Level At Grand Palladium Lady Hamilton Resort & Spa

4.5 out of 5
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.6/10 Excellent! (75 reviews)
We loved the property and staff were eager to help fix our reservation.

Reviewed on Jun 29, 2025

El Colonial - Adults Only

El Colonial - Adults Only

3.5 out of 5
Old San Juan
per person
Aug 16 - Aug 26
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to San Juan (SJU)
9.4/10 Exceptional! (1,215 reviews)
This hotel was amazing

Reviewed on Jul 8, 2025

Ocean Eden Bay - Adults Only - All inclusive

Ocean Eden Bay - Adults Only - All inclusive

5 out of 5
per person
Sep 30 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Montego Bay (MBJ)
8.2/10 Very Good! (3,323 reviews)
AMAZING! Beautiful property, super friendly staff. Will be back!!

Reviewed on Jul 8, 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4 out of 5
Condado
per person
Aug 16 - Aug 26
found 18 hours ago
Roundtrip flight included
Tokyo (TYO) to San Juan (SJU)
8.8/10 Excellent! (495 reviews)
Excellent service. Staff very kind. Room was great!

Reviewed on Jul 7, 2025

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
8.8/10 Excellent! (1,001 reviews)
"Excellent location."

Reviewed on Jun 28, 2025

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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 ￥30,710 per night from Jul 9 to Jul 10
￥30,710
￥45,845 total
Jul 9 - Jul 10
includes taxes & fees
8.6/10 Excellent! (1,731 reviews)
"Great location, shopping and dining just a few blocks away from the hotel. Be careful with taxi drivers, they abuse their fares when you are tourist. Ask how much before get in the car."

Reviewed on Jul 7, 2025

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
Fully refundableReserve now, pay when you stay
The price is ￥27,384 per night from Aug 4 to Aug 5
￥27,384
￥35,361 total
Aug 4 - Aug 5
includes taxes & fees
9/10 Wonderful! (1,012 reviews)
"Great location! Staff was super friendly, room was clean with a great view, the restaurants were also a great perk!"

Reviewed on Jul 6, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 80,862 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.