A beach with clear turquoise water, white sand, and palm trees.

Caribbean Islands Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top destinations in Caribbean Islands

The Latest Caribbean Islands Holiday Packages

Price found within the past 48 hours. Click for updated prices.
  • 19 Sept - 22 Sept

    Casa de Campo Resort and Villas + Flight

    La Romana
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,042 reviews)
    Return Chicago (ORD) - Punta Cana (PUJ)
    ORD - PUJDirect PUJ - ORD1 stop
    €1,372
    €694
    per traveller
    found 1 day ago
    Casa de Campo Resort and Villas
  • 19 Sept - 23 Sept

    Hotel Riu Palace Macao - Adults Only - All Inclusive + Flight

    Bávaro
    4 nights
    4.5 star property
    8.6/10 - Excellent (1,113 reviews)
    "The rooms were not cleaned properly, and I had to switch rooms three times. The staff was not helpful in resolving the issues. The food was below average and did not meet my expectations. Overall, my stay was disappointing."
    Reviewed July 30, 2026
    Return Chicago (ORD) - Punta Cana (PUJ)
    ORD - PUJDirect PUJ - ORD1 stop
    €1,628
    €947
    per traveller
    found 1 day ago
    Hotel Riu Palace Macao - Adults Only - All Inclusive
  • 19 Sept - 23 Sept

    Hotel Riu Palace Bavaro - All Inclusive + Flight

    Bávaro
    4 nights
    4.5 star property
    8.6/10 - Excellent (2,537 reviews)
    "Amazing would go again"
    Reviewed July 31, 2026
    Return Chicago (ORD) - Punta Cana (PUJ)
    ORD - PUJDirect PUJ - ORD1 stop
    €1,517
    €952
    per traveller
    found 1 day ago
    Hotel Riu Palace Bavaro - All Inclusive
  • 18 Sept - 21 Sept

    Iberostar Selection Bávaro Suites - All Inclusive + Flight

    Bávaro
    3 nights
    5.0 star property
    8.2/10 - Very good (1,001 reviews)
    "Multiple stays at this hotel love it for the beach and food has the best beach by far out of any of the other hotels located on the strip rooms could use a little updating but not a huge factor in our stay"
    Reviewed July 30, 2026
    Return Chicago (ORD) - Punta Cana (PUJ)
    ORD - PUJDirect PUJ - ORD1 stop
    €1,111
    €702
    per traveller
    found 1 day ago
    Iberostar Selection Bávaro Suites - All Inclusive
  • 18 Sept - 21 Sept

    Moon Palace The Grand - Punta Cana - All Inclusive + Flight

    Punta Cana
    3 nights
    4.5 star property
    6.6/10 - (14 reviews)
    Return Chicago (ORD) - Punta Cana (PUJ)
    ORD - PUJDirect PUJ - ORD1 stop
    €1,714
    €1,132
    per traveller
    found 20 hours ago
    Moon Palace The Grand - Punta Cana - All Inclusive

Discover the most popular places to visit in Caribbean Islands

What to do in Caribbean Islands

Caribbean Islands Hotel Deals

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

How much does a Caribbean Islands holiday package cost?

Perhaps much less than you think — from only €694, as a matter of fact! By combining hotels, flights and car rentals into your own custom-built holiday package, your getaway to Caribbean Islands is only clicks away.

How do I get a cheap travel package to Caribbean Islands?

One of the easiest ways to save cash (and time) is to bundle your bookings with Expedia. Flights, hotels, rental cars and activities — we've got it all. Select a combination that best suits you and see your savings grow. We know a travel package is never a one-size-fits-all. That's why we offer over 550 air carriers and 1,000,000 hotel options throughout the world, which lets you customize your Caribbean Islands adventure.

What are the top hotels in Caribbean Islands?

Check out Christopher Hotel and Le Sereno. They're top picks for lots of travellers to St. Barthelemy. If San Juan is on your itinerary, Costa Bahia Hotel Paseo Caribe and La Concha Renaissance San Juan Resort are two top-notch options.

How far in advance should I book my Caribbean Islands holiday?

Reserving your flight early with Expedia means one less thing to have to worry about. Most carriers advertise prices up to 12 months prior to departure dates. This is often the cheapest time to book. If circumstances have left you booking late, discount prices to Caribbean Islands sometimes become available in the weeks leading up to departure.

What does an Expedia Caribbean Islands travel package include?

Rental cars, hotels and flights, or any combination of the three — it's your pick! Whether you're exploring Caribbean Islands with the entire family or travelling by yourself, there's a bundle to suit your budget and style. Once you've made your booking, why not add on a couple of tours as well?

What should I know before booking a Caribbean Islands travel package?

So many places to venture to, so many things to see and do. With a package, you'll be able to tick more of them off your list. Combine your flights, rental cars and hotels and score big savings.

Can I choose my airline with a Caribbean Islands Expedia holiday package?

With a holiday package, you're always in charge. Whether you're looking to fly to Caribbean Islands in coach or business class, simply choose from the available airline options. Expedia has access to over 550 partner airlines worldwide.

If I'm not able to travel, can I cancel my Caribbean Islands holiday package?

Whether it's your hotel or flight, yes, you can amend or cancel it. Locked in your Caribbean Islands holiday package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a charge from your hotel, airline or car rental company. For more information, take a look at our Customer Service Portal. We're here to help you every step of the way.

Book with confidence

Things to do in Caribbean Islands

The Caribbean Islands offer a delightful mix of beach relaxation and cultural exploration, perfect for outdoor enthusiasts. Engage in unforgettable adventures with activities like snorkelling, scuba courses, and thrilling adventure sports. Explore recreational areas and indulge in fun activities that showcase the vibrant spirit of the islands, ensuring a memorable vacation experience.

Best time to go to Caribbean Islands

The best time to visit Caribbean Islands depends on your weather preferences. The hottest average temperature around Caribbean Islands is in September, when weather is mostly sunny and rainfall is light rain. The coolest average temperature around Caribbean Islands is in November when weather is mostly sunny and rainfall is light rain.

Tips to save on your trip to Caribbean Islands

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.