Caribbean Holidays from NZ$2,037

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Top destinations in Caribbean

Dominican Republic featuring general coastal views and a sunset
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Santo Domingo

Santo Domingo

The Latest Caribbean Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Ciqala Suites Hotel

Ciqala Suites Hotel

4 out of 5
Santurce
per person
6 Sept - 10 Sept
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
7.4/10 Good! (1,004 reviews)
I just spend on night here but everything from check in to the complimentary breakfast has bean excellent. I would stay here again and gladly recommend for anyone to stay here.

Reviewed on 4 Jul. 2025

Dorado Beach 5 Bedroom Villa

Dorado Beach 5 Bedroom Villa

3.5 out of 5
Higuillar
per person
6 Sept - 10 Sept
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
No reviews
Serena Boutique Hotel

Serena Boutique Hotel

3.5 out of 5
per person
6 Sept - 13 Sept
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
9.6/10 Exceptional! (201 reviews)
The family that owns this beautiful place were the sweetest most accommodating, helpful people ever! We didn’t rent a car so they ran to the store and bought us whatever we needed, took us on a 4 hour tour, cooked amazing breakfast’s each morning. I could not have picked a better place to stay on our honeymoon! And I will be coming back every year!

Reviewed on 18 Jul. 2025

OLV Fifty Five - Adults Only

OLV Fifty Five - Adults Only

4 out of 5
Condado
per person
6 Sept - 10 Sept
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
8.8/10 Excellent! (500 reviews)
Very pretty the property

Reviewed on 20 Jul. 2025

Aire de O:live

Aire de O:live

4 out of 5
Isla Verde
per person
6 Sept - 10 Sept
found 5 hours ago
Return direct flight included
Los Angeles (LAX) to San Juan (SJU)
9.2/10 Wonderful! (193 reviews)
We had to check in super late due to massive delays. Front desk didn’t provide a warm welcome which was likely due to it being so late. But nonetheless we were awaken by construction at 10am for 3 days straight with no warning from the hotel and they are still under construction. Aside from that, hotel is clean but it is small with paper thin walls.

Reviewed on 19 Jul. 2025

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
8.8/10 Excellent! (1,002 reviews)
"Best place ever"

Reviewed on 17 Jul. 2025

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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$581 per night from 21 July to 22 July
NZ$581
21 July - 22 July
includes taxes & fees
8.6/10 Excellent! (1,780 reviews)
"Beautiful hotel. Room was very small and quite loud being on 2nd floor in front by parking lot. Room was decorated nicely. Bathroom was very small and zero counter space or space to put any of your belongings. No shower curtain which looks great but makes wet mess of bathroom no matter how careful ..."

Reviewed on 19 Jul. 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$345 per night from 27 July to 28 July
NZ$345
27 July - 28 July
includes taxes & fees
9/10 Wonderful! (1,028 reviews)
"Hotel staff very friendly , market \ bistro restaurant staff very unpleasant."

Reviewed on 16 Jul. 2025

Hotel Rumbao, a Tribute Portfolio Hotel
See all 81,371 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.