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Caribbean vacation packages.

Southwest Vacations® offers spectacular vacation deals to the Caribbean. With a variety of exciting destinations and amazing accommodations, you can create an ideal tropical all-inclusive vacation package.

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Featured deals to the Caribbean

Featured deals to the Caribbean

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  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 40%
    25% discount on spa services + free in-room breakfast + $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
    Sep 7, 2024
    5 nights hotel + flight from
    $2,058 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Savings up to $300
    Riu Palace Tropical Bay - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    Sep 8, 2024
    5 nights hotel + flight from
    $1,411 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Savings up to $300
    Royalton Blue Waters Montego Bay, An Autograph Collection - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    Sep 15, 2024
    5 nights hotel + flight from
    $1,660 per person
  • Save up to 40%
    $200 in resort coupons + free in-room breakfast + 25% spa discount
    Dreams Flora Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Dominican Republic, Punta Cana

    Best priced departure dates
    Sep 9, 2024
    5 nights hotel + flight from
    $1,158 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 25%
    Resort credits up to $800 + free private roundtrip transfers
    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
    Sep 9, 2024
    5 nights hotel + flight from
    $1,594 per person
  • Hard Rock Hotel and Casino Punta Cana - All-Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Dominican Republic, Punta Cana

    Best priced departure dates
    Sep 9, 2024
    5 nights hotel + flight from
    $1,487 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 40%
    25% discount on spa services + free in-room breakfast + $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
    Sep 8, 2024
    5 nights hotel + flight from
    $1,565 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    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
    Sep 13, 2024
    5 nights hotel + flight from
    $1,600 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Grand Palladium Jamaica Resort and Spa - All Inclusive
    4 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    2024: Sep 6, Sep 7
    5 nights hotel + flight from
    $1,449 per person
  • Royalton Negril, An Autograph Collection - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    Sep 8, 2024
    5 nights hotel + flight from
    $1,434 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Save up to 40%
    25% discount on spa services + free in-room breakfast + $200 in resort coupons
    Secrets Wild Orchid Montego Bay - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    Sep 8, 2024
    5 nights hotel + flight from
    $1,641 per person
  • TripAdvisor traveler rating
    based on TripAdvisor reviews
    Riu Palace Jamaica - All Inclusive
    5 star hotel
    TripAdvisor traveler rating
    based on TripAdvisor reviews
    All-inclusive

    Jamaica, Montego Bay

    Best priced departure dates
    Sep 8, 2024
    5 nights hotel + flight from
    $1,488 per person
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†First and second checked bags. Weight and size limits apply. A golf bag can be substituted for one checked bag.

Seats are limited and may not be available on some flights that operate during peak travel times and holiday periods. Flight and hotel rates may vary by day of week. Hotel surcharges may apply to weekends, holidays, and convention periods. Flights available on published, scheduled service only. Rates may be subject to change until purchased. Discounts are valid per reservation before taxes are applied. Offer not valid on existing reservations and may not be combined with any other offer. Subject to availability. Restrictions apply. ALG Vacations Corp. is the tour operator for Southwest Vacations®.