Caribbean Vacations & Trips

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NT$5,067 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Caribbean

FlightsFlightsHotelsHotels

Punta Cana

Punta Cana

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
The price is NT$8,424 per night from May 11 to May 12
NT$8,424
per night
May 11 - May 12
9/10 Wonderful! (1,002 reviews)
Complementary coffee was delicious.

Reviewed on 2026/4/15

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 NT$6,959 per night from May 17 to May 18
NT$6,959
per night
May 17 - May 18
8.6/10 Excellent! (2,473 reviews)
Very clean rooms and helpful stuff. The dining room service was a little slow with a few bill errors.

Reviewed on 2026/4/15

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 NT$6,536 per night from May 17 to May 18
NT$6,536
per night
May 17 - May 18
9/10 Wonderful! (1,634 reviews)
Hotel Rumbao was so beautiful and in the perfect location. It was very easy to navigate everywhere in Old San Juan from the hotel. The room was very clean and all of the staff we encountered were helpful and friendly. Our window view was great! The pool was on the top floor and was a little crowded ...

Reviewed on 2026/4/14

Hotel Rumbao, a Tribute Portfolio Hotel
See all 85,362 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.