Accessbility Statement Skip to Main Content

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.

Rooms - Travelers

Caribbean Vacation Package Deals

Caribbean Vacation Package Deals

Traveling Between
and
Traveling Between
Prev
June 2025
SuMoTuWeThFrSa
1234567
891011121314
15161718192021
22232425262728
2930     
Next
July 2025
SuMoTuWeThFrSa
  12345
6789101112
13141516171819
20212223242526
2728293031  
Filter Your Search
Filter Your Search
Filter Your Search
All-Inclusive Only
Traveling Between
and
Traveling Between
Prev
June 2025
SuMoTuWeThFrSa
1234567
891011121314
15161718192021
22232425262728
2930     
Next
July 2025
SuMoTuWeThFrSa
  12345
6789101112
13141516171819
20212223242526
2728293031  
Hotel Class
Number of Nights
-
$
Enter atleast $112
Sort by
All-Inclusive Only
-
$
Enter atleast $112
Hotel Class
Number of Nights
  • Dreams Playa Esmeralda Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    2025: Sep 2 - Sep 9, Sep 11 - Sep 16, Sep 18 - Sep 21, Sep 25 - Sep 29
    3 Nights Hotel From
    $523 per person Includes Taxes + Fees
  • Secrets Playa Esmeralda Resort & Spa - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    2025: Aug 1, Aug 2, Aug 9, Aug 11, Aug 13, Aug 15
    3 Nights Hotel From
    $583 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes savings up to 58%
    Riu Republica Adults Only - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Dominican Republic, Punta Cana

    Best Priced Departure Dates
    2025: Sep 15, Sep 29
    3 Nights Hotel From
    $279 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Limited time Steal of a Deal
    The Verandah Antigua - All Inclusive
    4 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Antigua

    Best Priced Departure Dates
    2025: Aug 17, Aug 23, Aug 24, Aug 26, Aug 30, Sep 1 - Sep 4, Sep 8, Sep 10
    3 Nights Hotel From
    $706 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Limited time Steal of a Deal
    Wyndham Grand Barbados Sam Lords Castle All Inclusive Resort
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews

    Barbados

    Best Priced Departure Dates
    2025: Jul 15, Jul 17, Jul 22 - Jul 30 (Tue, Wed Departures); Jul 25, Aug 3, Aug 6, Aug 7, Aug 11, Aug 14, Aug 16, Aug 19 - Aug 24, Aug 26, Aug 28, Sep 1, Sep 3, Sep 6, Sep 7, Sep 9, Sep 13
    3 Nights Hotel From
    $776 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Limited time Steal of a Deal
    Dreams Curacao Resort, Spa & Casino - All Inclusive
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Curacao

    Best Priced Departure Dates
    Sep 1, 2025
    3 Nights Hotel From
    $392 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Limited time Steal of a Deal
    Bahia Principe Luxury Runaway Bay Adults Only - All Inclusive
    4.5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2025: Aug 24, Aug 26, Aug 28, Aug 31, Sep 2, Sep 3, Sep 7, Sep 9 - Sep 13, Sep 16, Sep 18, Sep 20, Sep 21, Sep 24 - Sep 29
    4 Nights Hotel From
    $702 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Includes savings up to 40%
    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
    Aug 24, 2025
    4 Nights Hotel From
    $1,098 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Limited time Steal of a Deal
    Riu Palace Aquarelle
    5 star hotel
    TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    All-Inclusive

    Jamaica, Montego Bay

    Best Priced Departure Dates
    2025: Aug 19, Aug 24
    4 Nights Hotel From
    $698 per person Includes Taxes + Fees
  • TripAdvisor Traveler Rating
    based on TripAdvisor Reviews
    Limited time Steal of a Deal
    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
    2025: Sep 2, Sep 3, Sep 6, Sep 7, Sep 9 - Sep 13, Sep 16, Sep 18, Sep 20, Sep 21, Sep 24 - Sep 27
    4 Nights Hotel From
    $838 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

    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.
    View Deals

  • 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.
    View Deals

  • 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.
    View Deals

  • 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.
    View Deals

  • 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.
    View Deals

  • 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.
    View Deals

  • 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?
    View Deals

  • Puerto Rico

    European charm, Latin flare, stunning attractions, and tropical landscapes - Puerto Rico combines the best of everything.
    View Deals

  • Punta Cana

    Leave your wallet in your room. The luxury of Punta Cana in the Dominican Republic is all-inclusive.
    View Deals

  • 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.
    View Deals

  • 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.
    View Deals

  • St. Maarten (St. Martin)

    This tropical hotspot is bursting with French and Dutch culture, attractions, amazing local restaurants, and pristine beaches along the ocean.
    View Deals

  • Turks & Caicos

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

  • 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.
    View Deals