Caribbean Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to Rp16.000.000 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

A marina with a white boat named 'Achina' docked, surrounded by palm trees and a building with a green roof.
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Punta Cana

Punta Cana
A pier with kayaks and a sailboat.
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Montego Bay

Montego Bay

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
The price is Rp3.324.352 per night from 13 Jul to 14 Jul
Rp3.324.352
Rp4.348.288 total
13 Jul - 14 Jul
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
"It's a beautiful, historical hotel. It was a pleasure to stay in it. Highly recommend."

Reviewed on 23 Jun 2026

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 Rp3.324.531 per night from 21 Jul to 22 Jul
Rp3.324.531
Rp5.076.048 total
21 Jul - 22 Jul
includes taxes & fees
8.6/10 Excellent! (2,706 reviews)
"Decent location, but I probably wouldn't walk around after dark. I was traveling for work and stayed 3 nights. Had the airline change my flight half way through my stay and let the hotel know right away. I ended up having to leave a day early. The hotel charged me full price for the night, added ..."

Reviewed on 27 Jun 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
Fully refundableReserve now, pay when you stay
The price is Rp2.790.814 per night from 15 Jul to 16 Jul
Rp2.790.814
Rp3.794.711 total
15 Jul - 16 Jul
includes taxes & fees
9/10 Wonderful! (1,743 reviews)
"Clean, comfortable, will stay again. Great location. Pool was never crowded."

Reviewed on 27 Jun 2026

Hotel Rumbao, a Tribute Portfolio Hotel
See all 87,437 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.

Stay near popular Caribbean attractions

An old church with a tiled roof, stone walls, and two bell towers.

Altos de Chavon Village

A replica 16th-century Mediterranean village perched on a rocky outcrop above the River Chavón.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.