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.
FlightsFlightsHotelsHotels

Punta Cana

Punta Cana
A pier with kayaks and a sailboat.
FlightsFlightsHotelsHotels

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 Rp3.324.166 per night from 21 Jul to 22 Jul
Rp3.324.166
Rp4.348.045 total
21 Jul - 22 Jul
includes taxes & fees
9.2/10 Wonderful! (1,006 reviews)
"My husband and I were married here so this hotel is special to us. We always have a wonderful stay when we go. It’s our favorite place in Old San Juan. The bed is comfortable and the location is great."

Reviewed on 18 Jul 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 Rp3.198.899 per night from 3 Aug to 4 Aug
Rp3.198.899
Rp4.917.703 total
3 Aug - 4 Aug
includes taxes & fees
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 Rp3.693.518 per night from 22 Jul to 23 Jul
Rp3.693.518
Rp4.778.617 total
22 Jul - 23 Jul
includes taxes & fees
9/10 Wonderful! (1,798 reviews)
"Comfortable and clean room. Staff is very friendly with excellent customer service."

Reviewed on 20 Jul 2026

Hotel Rumbao, a Tribute Portfolio Hotel
See all 87,625 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

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.