A tropical beach with clear turquoise waters, lush green hills, and a small red building on a hill.

Caribbean Casino Vacations

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The Latest Caribbean Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Dec 10 - Dec 15

    El Beso Adults Only At Ocean El Faro - All Inclusive + Flight

    Uvero Alto
    5 nights
    5.0 star property
    8.6/10 - Excellent (1,369 reviews)
    "**A Wonderful Stay – Highly Recommend!** We had a great time at this beautiful resort! There were lots of restaurants to choose from, great drinks and plenty of activities to keep us entertained. A special thank you to our concierge, **José ** who was fantastic! He was always so friendly, helpful and prompt in answering any questions. He took care of our dinner reservations and arranged transportation to and from our room, making everything so easy and our stay that much more enjoyable. We..."
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Punta Cana (PUJ)
    YYZ - PUJ • Nonstop PUJ - YYZ • 1 stop
    ¥280,733
    ¥146,486
    per traveler
    found 12 hours ago
    El Beso Adults Only At Ocean El Faro - All Inclusive
  • Dec 10 - Dec 15

    Hotel Riu Palace Punta Cana - All Inclusive + Flight

    Bávaro
    5 nights
    4.0 star property
    8.4/10 - Very good (2,466 reviews)
    "Estuvo muy bien todo en general, si tengo una ligera sugerencia,había muy pocas opciones para distraerse o pasar el tiempo en las noches , debe ser más alegre"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Punta Cana (PUJ)
    YYZ - PUJ • Nonstop PUJ - YYZ • 1 stop
    ¥609,834
    ¥199,675
    per traveler
    found 12 hours ago
    Hotel Riu Palace Punta Cana - All Inclusive
  • Dec 10 - Dec 15

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

    Bávaro
    5 nights
    5.0 star property
    8.2/10 - Very good (3,021 reviews)
    "Clean room"
    Reviewed November 8, 2026
    Roundtrip • Toronto (YYZ) - Punta Cana (PUJ)
    YYZ - PUJ • Nonstop PUJ - YYZ • 1 stop
    ¥477,084
    ¥237,783
    per traveler
    found 12 hours ago
    Hard Rock Hotel & Casino Punta Cana an All-Inclusive Resort
  • Dec 10 - Dec 15

    Ocean Blue & Sand Beach Resort - All Inclusive + Flight

    Bávaro
    5 nights
    4.5 star property
    8.6/10 - Excellent (6,276 reviews)
    "Perfecto"
    Reviewed November 9, 2026
    Roundtrip • Toronto (YYZ) - Punta Cana (PUJ)
    YYZ - PUJ • Nonstop PUJ - YYZ • 1 stop
    ¥304,435
    ¥155,271
    per traveler
    found 12 hours ago
    Ocean Blue & Sand Beach Resort - All Inclusive
  • Dec 10 - Dec 15

    Ocean El Faro Resort - All Inclusive + Flight

    Uvero Alto
    5 nights
    5.0 star property
    8.4/10 - Very good (4,354 reviews)
    "Me agrado todo en general, me hubiera gustado más actividades diarias"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YYZ) - Punta Cana (PUJ)
    YYZ - PUJ • Nonstop PUJ - YYZ • 1 stop
    ¥291,415
    ¥154,278
    per traveler
    found 12 hours ago
    Ocean El Faro Resort - All Inclusive

Discover the most popular places to visit in Caribbean

Caribbean 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.

FAQs for Carribean cheap vacation packages

When is the best time of year to go to the Caribbean?

One of the best times to visit the Caribbean is from December to May when the sun is out, the air cool, and the water nice and warm. It can get a bit busy during Christmas, Thanksgiving, and the school holidays. If you're planning a cheap Caribbean family vacation it can be worth looking for travel dates outside of these busier periods. June to November is the rainier season, which typically means very few crowds and the opportunity to snag cheap Caribbean vacation deals for an island getaway on a budget.

How to find cheap Caribbean vacation packages on Expedia?

One of the best ways to find cheap family vacations in the Caribbean is to be flexible with your travel dates and destination. Popular islands such as Aruba and the Bahamas can be on the pricey side during the high season. But prices for accommodations and airfare often dramatically drop outside of the busier months, when airlines and hotels are trying to fill up their seats and rooms. With Expedia, effortlessly compare your travel dates and find top cheap Caribbean vacation deals.

Which Caribbean island is most affordable?

When you're looking for cheap Caribbean vacations, Jamaica is usually a safe bet. Enjoy pristine white-sand beaches, delicious local cuisine, and the strong musical heritage of reggae that can be heard all over the island. Another paradise for cheap Caribbean vacations, the Dominican Republic, is all about palm trees, crystal-clear water, and a lively local nightlife scene where you can taste some of the best rums in the world.

How to travel to the Caribbean affordably?

Expedia gives you access to some of the cheapest and best Caribbean vacations on the market by bundling your flights and hotels to save you money. Enjoy exclusive discounts and extras, from free car rental to hotel nights on the house. From all-inclusive, adults-only vacations at Riu Palace Paradise Island to the majestic The Royal at Atlantis, explore a world of cheap Caribbean island vacations with Expedia.

Why should I choose a vacation package?

With a vacation package, you save both time and money. Expedia is your one-stop shop for booking your entire trip from start to finish. Easily find your flights and accommodations, add car rental, book activities and tickets for popular local attractions, and save money along the way. When you book cheap Caribbean all-inclusive vacation packages, all that's left to do for you is to rock up to the airport in time for your flight and let the fun in the sun begin.

How to find cheap last-minute deals on Expedia?

To find last-minute deals for some of the best cheap vacations in the Caribbean, search for your preferred destination and travel dates. In your search results, look out for the small green tags above the price. These tell you how much you are saving with your package. When you book last-minute cheap Caribbean vacations with Expedia, you'll enjoy incredible savings from free flights to thousands of dollars of discount on the total cost of your trip.

Can I cancel my package booking?

Your plans can change. As one of the world's leading travel booking platforms, Expedia understands that you need flexibility. If you've booked a vacation package such as a cheap Caribbean vacation to Puerto Rico and need to cancel, simply log into your account and head to the “Trips” section. There you can cancel, amend, or add extras to your trip. You may be charged a cancellation fee depending on the type of package that you have booked. Please carefully read your cancellation policy before booking.

Why should I book my Caribbean vacation with Expedia?

With Expedia, enjoy privileged access to one of the world's largest selections of vacation packages, including cheap family Caribbean vacations in some of the most picture-postcard islands in the Caribbean Sea. If you've spotted a particularly great package, you can book now and pay later, and make the most of fantastic savings while the deal is still hot off the press.

What are some of the best things to do in the Caribbean for budget travelers?

The Caribbean is much more than a luxury getaway experience. If you want to plan one of the best Caribbean vacations for cheap, make the most of self-guided street food tours and sample local delicacies such as Barbados' cou-cou and flying fish and Antigua's bread pudding. For a very modest entry fee, hike through tropical forests and cloud-capped mountains in Jamaica's Blue and John Crow Mountains National Park. And of course, enjoy a bounty of free beaches and the always stunning spectacle of the sun going down over the horizon.