Caribbean Vacations & Trips

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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

Caribbean Hotel Deals

Hotel El Convento

Hotel El Convento

4.5 out of 5
100 Cristo St San Juan
The price is NT$5,870 per night from Sep 21 to Sep 22
NT$5,870
NT$7,678 total
Sep 21 - Sep 22
includes taxes & fees
9.2/10 Wonderful! (1,005 reviews)
"The beautiful building and historic structure"

Reviewed on 2026/9/13

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 NT$5,122 per night from Sep 16 to Sep 17
NT$5,122
NT$8,020 total
Sep 16 - Sep 17
includes taxes & fees
8.6/10 Excellent! (3,036 reviews)
"The hotel is very pretty and clean, The staff is also very helpful. The rooms have no mirrors and the was not shower curtain for the shower. The restaurants are also very expensive. The Wood Rogers Tavern was the only thing the was open during my stay and it was good. The Brunch was $80 with tax ..."

Reviewed on 2026/9/15

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 NT$4,541 per night from Sep 27 to Sep 28
NT$4,541
NT$6,369 total
Sep 27 - Sep 28
includes taxes & fees
9/10 Wonderful! (1,930 reviews)
"Excellent stay for me and my teenage daughter. Every interaction was very pleasant, friendly, and helpful. Property has vast options for relaxing in calm quiet peace, or having fun throughout the day and night. Food options were all amazing. We had dinner at a different restaurant each night and ..."

Reviewed on 2026/9/14

Hotel Rumbao, a Tribute Portfolio Hotel
See all 88,844 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.

Stay near popular Caribbean attractions

A beach scene with a flag, beach chairs, umbrellas, and a vendor cart.

Eagle Beach

9.4/10 (6,014 reviews)
Spot fish swimming in the crystal-clear waters, look for turtle nests on the shore and photograph Aruba’s famous windswept divi-divi trees.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.