Caribbean Holidays 2026

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Top destinations in Caribbean

Top hotels in Caribbean

Hotel El Convento

100 Cristo St San Juan

Fully refundableReserve now, pay when you stay

Rp3.746.849

Rp4.900.915 total

1 Jul - 2 Jul

includes taxes & fees

9.2/10 Wonderful! (1,016 reviews)

"An awesome experience! Thanks for the upgrade! Very charming and service oriented staff."

Reviewed on 14 Jun 2026

British Colonial - Nassau

Number One Bay St Nassau

Fully refundableReserve now, pay when you stay

Rp3.313.030

Rp5.058.488 total

22 Jun - 23 Jun

includes taxes & fees

8.6/10 Excellent! (2,656 reviews)

"Always accommodating friendly staff"

Reviewed on 15 Jun 2026

Hotel Rumbao, a Tribute Portfolio Hotel

100 Brumbaugh Street San Juan Puerto Rico

Fully refundableReserve now, pay when you stay

Rp2.854.028

Rp3.861.011 total

30 Jun - 1 Jul

includes taxes & fees

9/10 Wonderful! (1,715 reviews)

"Desayuno súper rico, y a pesar que sabíamos que SanJuan tenía problemas de agua, allí no faltó nunca , todo súper !! Volveremos pronto"

Reviewed on 14 Jun 2026

See all 87,105 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.