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

Caribbean Islands Vacations

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

Top Scuba Diving vacation packages in Caribbean Islands

Price found within the past 48 hours. Click for updated prices.
  • Aug 28 - Sept 2

    Casa de Campo Resort and Villas + Flight

    La Romana
    5 nights
    5.0 star property
    9.6/10 - Exceptional (1,039 reviews)
    Roundtrip Hamilton (YHM) - Punta Cana (PUJ)
    YHM - PUJ2 stops PUJ - YHM2 stops
    CA $2,819
    CA $1,622
    per traveller
    found 11 hours ago
    Casa de Campo Resort and Villas
  • Sept 13 - Sept 18

    Hard Rock Hotel & Casino Punta Cana an All-Inclusive Resort + Flight

    Bávaro
    5 nights
    5.0 star property
    8.2/10 - Very good (2,756 reviews)
    Roundtrip Toronto (YTO) - Punta Cana (PUJ)
    YYZ - SDQ1 stop SDQ - YYZ1 stop
    CA $4,009
    CA $2,130
    per traveller
    found 1 day ago
    Hard Rock Hotel & Casino Punta Cana an All-Inclusive Resort
  • Oct 8 - Oct 13

    Excellence El Carmen - Adults Only All Inclusive + Flight

    Uvero Alto
    5 nights
    5.0 star property
    9.0/10 - Wonderful (3,233 reviews)
    "Super"
    Reviewed July 29, 2026
    Roundtrip Hamilton (YHM) - Punta Cana (PUJ)
    YHM - PUJ2 stops PUJ - YHM2 stops
    CA $3,421
    CA $1,992
    per traveller
    found 1 day ago
    Excellence El Carmen - Adults Only All Inclusive
  • Sept 3 - Sept 9

    Moon Palace Jamaica – All Inclusive + Flight

    Ocho Rios
    6 nights
    5.0 star property
    8.4/10 - Very good (2,090 reviews)
    "Beautiful beach! 4/5 for food"
    Reviewed July 29, 2026
    Roundtrip Hamilton (YHM) - Montego Bay (MBJ)
    YHM - MBJ1 stop MBJ - YHM1 stop
    CA $6,227
    CA $3,692
    per traveller
    found 13 hours ago
    Moon Palace Jamaica – All Inclusive
  • Oct 8 - Oct 13

    Excellence Punta Cana - Adults Only All Inclusive + Flight

    Uvero Alto
    5 nights
    5.0 star property
    9.2/10 - Wonderful (2,818 reviews)
    Roundtrip Hamilton (YHM) - Punta Cana (PUJ)
    YHM - PUJ2 stops PUJ - YHM2 stops
    CA $3,218
    CA $1,924
    per traveller
    found 1 day ago
    Excellence Punta Cana - Adults Only All Inclusive

Discover the most popular places to visit in Caribbean Islands

Top Scuba Diving Caribbean Islands Hotels

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 amazing mountains vacations in Caribbean Islands

How to plan for a mountain vacation in Caribbean Islands?

The first step to planning your mountain vacation to Caribbean Islands is to decide what dates you want to go. In the winter months, fresh snowfall means you could hit the slopes at ski resorts near Caribbean Islands, while summer invites you to enjoy scenic hikes. It's a good idea to choose the type of accommodation you'd prefer, too. On Expedia, you'll encounter a vast array of options in Caribbean Islands, from famous chain hotels to charming cabins. The vacation planning page has more tips for organizing your Caribbean Islands mountain vacation.

What amenities should I look for when booking a mountain resort in Caribbean Islands?

When booking accommodation for your mountain vacation to Caribbean Islands, check to see if where you're staying has heating. Caribbean Islands's mountain air means it can feel fresh at night. If you're craving a special stay, look to see if the hotel offers mountain view rooms, or has a pool or hot tub to unwind in the evenings. Expedia's handy search filters include all these amenities and more, making it a breeze to book the right place to stay on your Caribbean Islands vacation package.

Why should I choose a package for my mountain vacation in Caribbean Islands?

Choosing a package for your Caribbean Islands vacation often works out cheaper thanks to the savings you get for bundling up your flights and hotel. You'll typically find it costs more when booking these separately. On Expedia, the green label even shows you how much you're saving. Packages also tend to be more flexible, meaning it's more likely you can cancel for free in case your 2026 plans change. You can usually secure your package by paying a small upfront deposit, whereas booking flights separately requires full payment.

What does a Caribbean Islands package typically include?

Return flight tickets, your accommodation, and applicable taxes are typically included when you book a mountain vacation package to Caribbean Islands . Hotels may include breakfast and Wi-Fi, while the airfare may include checked luggage. Certain resorts may even include ski passes. As each Caribbean Islands vacation package is different, be sure to double-check what's included before you confirm. If you want a hassle-free trip, consider booking Caribbean Islands all-inclusive vacation packages as these include all meals.

How can I book my Caribbean Islands on Expedia?

Comparing some of the best deals using the search wizard is one of the first steps to booking your Caribbean Islands mountain vacation on Expedia. Take advantage of the search filters to narrow down hundreds of options at the click of a button. If you've got a strict budget, use the maximum price filter to set your limit. When you've pinned down your Caribbean Islands package vacation, book it in just a few clicks. You'll also have the option to spread the cost with Expedia's payment plans.

Why book your Caribbean Islands mountain vacation with Expedia?

With meaty exclusive deals you won't find anywhere else, you'll keep more cash in your pocket when booking your Caribbean Islands vacation package on Expedia. No matter your preferences or tastes, you'll find the right place to stay thanks to the wide selection of accommodation. There are even last-minute deals, too. And if that's not enough, join One Key for free. Expedia's reward program lets you earn points on eligible trips and also gives you access to juicy member-only discounts.

Can I cancel my mountain vacation package booking?

Yes, as most of Expedia's mountain vacation packages to Caribbean Islands are flexible, you can often cancel for free. Doing so is easy, too—log in to the “Trips” section and follow the steps. Don't forget to double-check the cancellation policy before booking, as not all Caribbean Islands vacation packages are flexible. The good news is Expedia will display this to you before payment. Take advantage of the free cancellation search filter so you'll be able to narrow down your search to view only flexible Caribbean Islands vacation packages.

What types of mountain accommodations are available in Caribbean Islands?

5-star hotels, cozy mountain lodges, and quaint bed and breakfasts are some of the most popular types of mountain accommodations for your vacation to Caribbean Islands. Don't forget to use the filters to home in the amenities you'd like to have, too. Maybe it's a spacious suite with a mountain view or a traditional lobby with a fireplace—you'll find it all with Expedia's easy-to-use search wizard and wide choice of accommodation.