Caribbean Holidays

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Top destinations in Caribbean

Dominican Republic featuring general coastal views and a sunset
FlightsFlightsHotelsHotels

Santo Domingo

Santo Domingo

Our pick of the best Caribbean Hotel Deals

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 NZ$644 per night from 22 Oct to 23 Oct
NZ$644
22 Oct - 23 Oct
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"It was perfect. Easy to walk everywhere and cheaper to use an uber. Very safe."

Reviewed on 5 Oct 2025

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 NZ$623 per night from 12 Oct to 13 Oct
NZ$623
12 Oct - 13 Oct
includes taxes & fees
8.6/10 Excellent! (1,977 reviews)
"Very clean. Beautiful view of beach. Staff were very polite, friendly, and helpful. Unfortunately, they were understaffed, and there were unusually long waits for meals and drinks to be served. Also, it rained all day on our second full day there, but hotel provided no umbrellas at all."

Reviewed on 5 Oct 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 NZ$372 per night from 26 Oct to 27 Oct
NZ$372
26 Oct - 27 Oct
includes taxes & fees
9/10 Wonderful! (1,191 reviews)
"Clean and very nice hotel, beds were super comfortable, staff was friendly and helpful, and accommodating of our needs and requests. The location was great for us, as we were cruising from the port adjacent to the hotel. The only negative for us was the lack of a lower priced option for breakfast ..."

Reviewed on 6 Oct 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 83,331 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.