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

Caribbean Islands Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Your Caribbean Islands Vacation

Leave the planning up to us with a Caribbean Islands vacation package. With everything arranged before you jet off, the only thing you'll need to do is sit back, relax and enjoy this destination's countless delights. Begin your trip to Caribbean Islands by spending a few nights in Punta Cana, one of the best cities here. When you're ready to stop dreaming and start travelling, Expedia will help turn your Caribbean Islands vacation into a reality.

The Latest Caribbean Islands Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Jan 6 - Jan 12

    Ocean Coral Spring - All Inclusive + Flight

    Falmouth
    6 nights
    5.0 star property
    8.4/10 - Very good (4,335 reviews)
    Roundtrip • Hamilton (YHM) - Montego Bay (MBJ)
    YHM - MBJ • 1 stop MBJ - YHM • Nonstop
    CA $4,231
    CA $1,724
    per traveller
    found 1 day ago
    Ocean Coral Spring - All Inclusive
  • Jan 31 - Feb 5

    Ocean Allure Eden Bay - Adults Only - All inclusive + Flight

    Falmouth
    5 nights
    5.0 star property
    8.4/10 - Very good (4,040 reviews)
    "Blah"
    Reviewed November 11, 2026
    Roundtrip • Toronto (YTO) - Montego Bay (MBJ)
    YYZ - MBJ • Nonstop MBJ - YYZ • Nonstop
    CA $6,166
    CA $2,314
    per traveller
    found 1 day ago
    Ocean Allure Eden Bay - Adults Only - All inclusive
  • Jan 19 - Jan 26

    Sunset at the Palms Resort - Adults Only - All Inclusive + Flight

    Negril
    6 nights
    4.5 star property
    9.2/10 - Wonderful (1,003 reviews)
    "We fell in love and will be back! Beautiful! Thanks for everything."
    Reviewed November 11, 2026
    Roundtrip • Hamilton (YHM) - Montego Bay (MBJ)
    YHM - KIN • 1 stop KIN - YHM • 1 stop
    CA $8,627
    CA $3,348
    per traveller
    found 1 day ago
    Sunset at the Palms Resort - Adults Only - All Inclusive
  • Jan 24 - Jan 30

    Live Aqua Punta Cana - All Inclusive - Adults Only + Flight

    Uvero Alto
    5 nights
    5.0 star property
    9.2/10 - Wonderful (2,461 reviews)
    "Everything was excellent and good quality, is a very lucky hotel"
    Reviewed November 11, 2026
    Roundtrip • Hamilton (YHM) - Punta Cana (PUJ)
    YHM - PUJ • 1 stop PUJ - YHM • 1 stop
    CA $5,708
    CA $2,424
    per traveller
    found 1 day ago
    Live Aqua Punta Cana - All Inclusive - Adults Only
  • Jan 24 - Jan 30

    Ocean Blue & Sand Beach Resort - All Inclusive + Flight

    Bávaro
    5 nights
    4.5 star property
    8.6/10 - Excellent (6,285 reviews)
    "An Amazing Experience – Highly Recommended! We had an absolutely wonderful stay at this resort! From the moment we arrived, we were welcomed with warmth, kindness, and genuine hospitality. The staff were exceptional, always friendly, welcoming, attentive, and ready to help with a smile. Their professionalism and dedication made our vacation even more special. A special thank you to the housekeeping team for keeping our room spotless and beautifully maintained every single day. The cleanliness..."
    Reviewed November 11, 2026
    Roundtrip • Hamilton (YHM) - Punta Cana (PUJ)
    YHM - PUJ • 1 stop PUJ - YHM • 1 stop
    CA $4,960
    CA $2,116
    per traveller
    found 1 day ago
    Ocean Blue & Sand Beach Resort - All Inclusive

Discover the most popular places to visit 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.

Find out more about Caribbean Islands

Things to do in Caribbean Islands

The Caribbean Islands are perfect for beach and culture-themed vacations, offering a variety of outdoor activities. Tourists can enjoy beach vacations, golf experiences, and beachfront relaxation, along with thrilling underwater sports like snorkeling. For those seeking adventure, the islands provide exciting island excursions. With a stunning natural backdrop, the Caribbean promises unforgettable experiences for every traveller.

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.

Frequently Asked Questions

How much does a Caribbean Islands vacation package cost?

Perhaps much less than you think — from only CA $1,724, as a matter of fact! By combining hotels, flights and car rentals into your own custom-built vacation 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 travelers 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 vacation?

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 traveling 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 vacation package?

With a vacation 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 vacation package?

Whether it's your hotel or flight, yes, you can amend or cancel it. Locked in your Caribbean Islands vacation 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.