Caribbean Holidays

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    Save up to Rp173.195 when you book a flight and hotel together*

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

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Top destinations in Caribbean

Dominican Republic featuring a sunset and general coastal views
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Santo Domingo

Santo Domingo
Bayahibe Beach which includes general coastal views
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Punta Cana

Punta Cana

Top hotels in Caribbean

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! (1,000 reviews)
This hotel stay would have received 5 stars if I had been informed of the main floor construction when I made the reservation. A timeless, beautiful hotel in a superb area of Old San Juan. I would stay here again when weddings aren't in full swing. A little tricky trying to get to one's room without ...

Reviewed on 18 Dec 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 Rp4.449.314 per night from 5 Jan to 6 Jan
Rp4.449.314
Rp6.435.104 total
5 Jan - 6 Jan 2026
includes taxes & fees
8.6/10 Excellent! (2,096 reviews)
Great historical hotel with modern amenities. Nice grounds and the pools, private beach right there too.

Reviewed on 23 Dec 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 Rp3.544.079 per night from 12 Jan to 13 Jan
Rp3.544.079
Rp4.566.336 total
12 Jan - 13 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,415 reviews)
The hotel had a nice breakfast option and bar option

Reviewed on 28 Dec 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 84,749 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 holiday package?
Your situation can change suddenly, so yes, you can. You may be able to change or cancel your Caribbean holiday 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 holiday 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 holiday?
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 travellers 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.