Caribbean Trips

  • Plan, book, travel with confidence

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    Better together

    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit

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

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

Top destinations in Caribbean

Dominican Republic showing general coastal views and a sunset
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Santo Domingo

Santo Domingo

Top hotels in Caribbean

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St, San Juan
8.8/10 Excellent! (1,002 reviews)
"The hotel is beautiful and the staff was so kind. The restaurant on site has great food and drinks. The location is perfect, walking distance to shops, restaurants and historical attractions."

Reviewed on Aug 5, 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 P9,084 per night from Aug 31 to Sep 1
P9,084
P14,270 total
Aug 31 - Sep 1
includes taxes & fees
8.6/10 Excellent! (1,860 reviews)
"From check in to check out, the staff was warm, professional, and attentive. They went above and beyond to make me feel welcome. I highly recommend this hotel. Conveniently located to everything!"

Reviewed on Aug 9, 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 P10,086 per night from Sep 9 to Sep 10
P10,086
P13,170 total
Sep 9 - Sep 10
includes taxes & fees
9/10 Wonderful! (1,084 reviews)
"Excellent place to stay."

Reviewed on Aug 11, 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 80,916 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.