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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.

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Caribbean Vacation Package Deals

Caribbean Vacation Package Deals

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  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes up to $250 in instant savings
    Bahia Principe Grand Jamaica - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes up to $250 in instant savings
    Bahia Principe Luxury Runaway Bay - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 20 - Dec 15
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes up to $500 in instant savings
    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
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    6th night free
    Includes up to $500 in instant savings
    Couples Negril - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    6th night free
    Includes up to $500 in instant savings
    Couples Sans Souci - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    6th night free
    Includes up to $500 in instant savings
    Couples Swept Away - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    6th night free
    Includes up to $500 in instant savings
    Couples Tower Isle - All-Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes up to $250 in instant savings
    Includes up to $600 in resort coupons
    Grand Lido Negril Au-Naturel, An Autograph Collection - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes up to $500 in instant savings
    Includes up to $1500 in resort credits
    Grand Palladium Jamaica Resort & Spa - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
  • Nonstop Vacation Deals
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes up to $500 in instant savings
    Includes up to $1500 in resort credits
    Grand Palladium Lady Hamilton Resort & Spa - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2024: Apr 22 - Aug 10
    3 Nights Hotel + Flight
    Get Price
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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
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews

    Punta Cana via Santo Domingo

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

    La Romana via Santo Domingo

    Iberostar Selection Hacienda Dominicus - All Inclusive

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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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.
  • 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?
  • Puerto Rico

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

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

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

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