Caribbean Holidays

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to NZ$545 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Top destinations in Caribbean

Find the Best Caribbean Holiday Packages

Have a warm island holiday at any time of year on your choice of lush tropical islands.

The Caribbean islands offer an amazing choice of beaches for tropical holidays, high-end shopping and fascinating cultures. Stop in major ports on a luxury cruise or charter a sailboat to hop from one to another of thousands of islands. Sunbathe on vast sandy shores. Scuba and snorkel in clear waters filled with colourful fish.

Beautiful beaches are common across the region, while art, architecture, cuisine and customs vary from island to island. Appreciate the pleasing mix of cultures of the indigenous island people and descendants of European settlers.

Aruba, Bonaire and Curaçao off the coast of Venezuela display Dutch influence. Have rijstaffel, a Dutch colonial meal of rice accompanied by 20 to 30 side dishes. Aruba has an unusually dry terrain, with miles of sandy beaches on the northwestern shores. Look for divi divi trees blown to the side in the region’s strong winds. Bonaire’s marine park and donkey sanctuary feature a range of wildlife. On Curacao, swim with dolphins and participate in extreme sports.

See the colourful buildings in old San Juan and the castles across the U.S. territory of Puerto Rico. St. Thomas of the U.S. Virgin Islands is a popular tour boat stop for buying diamonds and lazing on beaches. Nearby St. John is dominated by the Virgin Islands National Park, on land and in the underwater reefs. Learn about the 2,000 years of human occupants, including native Caribs, in the Salt River Bay National Historical Park on St. Croix.

For many people, Cuba has for decades been a land of mystery under Communist rule. While U.S. residents are not allowed to visit strictly for tourism, licensed visits can be arranged for various purposes. While here, see the cathedrals, squares and museums of Old Havana and visit exceptional beaches.

View the tropical plants in Hunte’s Gardens on Barbados. Dive and sample rum at a distillery on the Cayman Islands. Observe waterfalls and wildlife in the Dominican Republic. On the western side of the island, explore the Citadelle of Haiti. Golf, ride a bobsled and listen to steel drum music on Jamaica. Learn about Christopher Columbus and the native Arawaks while visiting the more than 700 islands of the Bahamas.

Most important of all, enjoy beach after beach after beach during the best Caribbean holidays.

Our pick of the best Caribbean Hotel Deals

Hotel Rumbao, a Tribute Portfolio Hotel
Hotel Rumbao, a Tribute Portfolio Hotel
4 out of 5
100 Brumbaugh Street, San Juan
Fully refundableReserve now, pay when you stay
The price is NZ$380 per night from 31 Mar to 1 Apr
NZ$380
per night
31 Mar - 1 Apr
7.6/10 Good! (1,011 reviews)
"Always Eccelent and outstanding location"

Reviewed on 22 Mar. 2024

Hotel Rumbao, a Tribute Portfolio Hotel
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$554 per night from 16 Apr to 17 Apr
NZ$554
per night
16 Apr - 17 Apr
8.6/10 Excellent! (1,009 reviews)
"The front desk staff were very helpful, professional and kind."

Reviewed on 28 Mar. 2024

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$594 per night from 9 Apr to 10 Apr
NZ$594
per night
9 Apr - 10 Apr
8.6/10 Excellent! (181 reviews)
"It was an upscale hotel. It was a great bargain. Dining options were a little pricey."

Reviewed on 28 Mar. 2024

British Colonial - Nassau
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.