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Caribbean Vacation Packages

They vary in landscape, size, and vibe, but each Caribbean island has a reason (or ten) for being on your bucket list. Discover your all-inclusive Caribbean vacation paradise.

They vary in landscape, size, and vibe, but each Caribbean island has a reason (or ten) for being on your bucket list. Discover your all-inclusive Caribbean vacation paradise.

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Caribbean Vacation Package Deals

Caribbean Vacation Package Deals

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  • Includes savings up to 58%
    Includes up to $762 in resort credits
    Hotel Riu Negril - AIl Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,017 per person Includes Taxes + Fees
  • Includes savings up to 50%
    Includes up to $600 in resort credits
    Iberostar Selection Rose Hall Suites - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,098 per person Includes Taxes + Fees
    • Accessible Resort
    Includes savings up to 45%
    Includes up to $600 in resort credits
    JOIA Rose Hall by Iberostar (Formerly Iberostar Grand Rose Hall) - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,387 per person Includes Taxes + Fees
  • Includes savings up to 65%
    Ocean Coral Spring - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,013 per person Includes Taxes + Fees
  • Includes savings up to 58%
    Includes up to $762 in resort credits
    Riu Palace Aquarelle - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,061 per person Includes Taxes + Fees
  • Includes savings up to 40%
    Includes up to $600 in resort credits
    JOIA Bavaro by Iberostar (Formerly Iberostar Grand Bavaro) - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,533 per person Includes Taxes + Fees
  • Exclusive Savings
    Ocean Blue & Sand - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $841 per person Includes Taxes + Fees
  • Includes savings up to 40%
    Includes up to $200 in resort coupons
    Breathless Montego Bay Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,491 per person Includes Taxes + Fees
  • Includes savings up to 45%
    Includes up to $600 in resort credits
    Iberostar Waves Rose Hall Beach - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 20, 2025
    3 Nights Hotel + Flight From
    $1,040 per person Includes Taxes + Fees
  • Includes savings up to 40%
    Includes up to $200 in resort coupons
    Secrets St. James Montego Bay - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    Jan 12, 2025
    3 Nights Hotel + Flight From
    $1,507 per person Includes Taxes + Fees
Not seeing deals? Modify your travel preferences, change your destination or select new dates.

There’s a reason the Caribbean islands are famous.

There are songs, movies, meals, and lifestyles that inspired the Caribbean islands. But do these pieces of paradise live up to the hype? You bet. And each Caribbean destination has its own unique qualities to lust after. So how do you choose the right one for your vacation? Well, we recommend visiting them all, eventually. But for now, these highlights of Caribbean vacations should help you narrow it down.

Featured Caribbean Vacations

  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews

    Kingston

    Secrets St. James Montego Bay - All Inclusive
    Book Now
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews

    Punta Cana via Santo Domingo

    Riu Palace Punta Cana - All Inclusive
    Book Now
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews

    La Romana via Santo Domingo

    Iberostar Selection Hacienda Dominicus - All Inclusive
    Book Now

The Islands of the Caribbean

  • Antigua

    The perfect blend of beaches, restaurants, adventure, and old world charm. Rendezvous Bay offers one of the best beaches in Antigua.
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  • Aruba

    This little desert island packs a lot of personality for you and your family. We dare you to run out of things to do.
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  • Bahamas

    In this lively area of the Caribbean, every day is a trip to the beach with plenty of attractions and nights on the town.
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  • Barbados

    Barbados hosts both British and Caribbean traditions, ranging from afternoon tea and cricket, to scuba and snorkeling on Dottins Reef, and a round of golf on designer oceanside courses. Soak up sun and history.
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  • Bermuda

    With 181 islands to explore and a wide variety of attractions and activities, your options are almost limitless. Bermuda is famous for pink-sand beaches like Elbow Beach and Horseshoe Bay.
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  • Grand Cayman

    If you love the ocean, the beach, good restaurants, and local attractions, then you’ll adore this island paradise. Stingray City is perfect for family friendly fun.
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  • Jamaica

    Reggae music, steel drums, amazing restaurants, beautiful beaches, and local festivals. Who wouldn’t want to vacation in the birthplace of the “no worries” mentality?
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  • Puerto Rico

    European charm, Latin flare, stunning attractions, and tropical landscapes - Puerto Rico combines the best of everything.
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  • Punta Cana

    Leave your wallet in your room. The luxury of Punta Cana in the Dominican Republic is all-inclusive.
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  • St. Kitts

    With so many things to do such as hiking, rock climbing, diving, relaxing on the beach, and enjoying local restaurants, you are sure to discover a unique perspective on culture, nature, and your vacation.
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  • St. Lucia

    Highlighted by the Piton Mountains and home to volcanic beaches, St. Lucia is paradise. Mother Nature made this twenty-seven-mile Caribbean island along the Atlantic ocean her masterpiece.
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  • St. Maarten (St. Martin)

    This tropical hotspot is bursting with French and Dutch culture, attractions, amazing local restaurants, and pristine beaches along the ocean.
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  • Turks & Caicos

    This laid-back string of islands is just a hop, skip, and a jump from the U.S. mainland.
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  • U.S. Virgin Islands

    In St. Croix, St. John, and St. Thomas, you will find all the shopping, beaching, snorkeling, dining, and relaxing your family is craving – with all the ease of domestic travel.
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