Caribbean Cruise Deals

Discover amazing cruise deals departing in the next 6 months. Updated weekly with the latest prices from major cruise lines!

⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 21, 2025
Duration 14 days
Starting from
$2,378
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Seashore

12 days, round-trip Caribbean Bahamas

Departure Dec 21, 2025
Duration 12 days
Starting from
$1,674
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Star

12 days, round-trip Caribbean Domincian Republic Grand Cayman

Departure Dec 24, 2025
Duration 12 days
Starting from
$1,532
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from Guadeloupe

Departure Dec 25, 2025
Duration 14 days
Starting from
$1,957
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⭐ Premium Deals Caribbean
Princess Cruises
Sky Princess

14 days, round-trip Eastern Caribbean Adventurer Holiday

Departure Dec 22, 2025
Duration 14 days
Starting from
$2,367
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⭐ Premium Deals Caribbean
MSC Explora Journeys Cruises
MSC Explora 2

14 days, round-trip An Extended Journey of Caribbean Festivities and West Indies Coastal Wonders

Departure Dec 22, 2025
Duration 14 days
Starting from
$10,730
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⭐ Premium Deals Caribbean
Seabourn Cruises
Seabourn Ovation

12 days, round-trip Southern Caribbean Holiday Aruba, Bonaire Curacao

Departure Dec 22, 2025
Duration 12 days
Starting from
$7,241
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⭐ Premium Deals
Silversea Cruises
Silver Ray

14 days, round-trip FortnbspLauderdale, Florida To FortnbspLauderdale, Florida

Departure Dec 23, 2025
Duration 14 days
Starting from
$8,750
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⭐ Premium Deals Caribbean
MSC Cruises
MSC Virtuosa

14 days, round-trip Southern Caribbean

Departure Dec 23, 2025
Duration 14 days
Starting from
$2,889
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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Grandeur

12 days, round-trip Merriment Joy In The Tropics Miami To Miami

Departure Dec 22, 2025
Duration 12 days
Starting from
$21,398
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⭐ Premium Deals
Celebrity Cruises
Celebrity Ascent

11 days, round-trip Panama Canal Perfect Day Holiday

Departure Dec 22, 2025
Duration 11 days
Starting from
$4,078
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Breakaway

12 days, round-trip Caribbean San Juan Puerto Plata

Departure Dec 23, 2025
Duration 12 days
Starting from
$2,199
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Jewel

12 days, round-trip Caribbean Curacao, Aruba Dominican Republic

Departure Dec 23, 2025
Duration 12 days
Starting from
$1,573
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Zuiderdam

11 days, round-trip Eastern Caribbean Windward Leeward Islands Holiday

Departure Dec 23, 2025
Duration 11 days
Starting from
$1,799
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⭐ Premium Deals Caribbean
Princess Cruises
Caribbean Princess

12 days, round-trip Panama Canal with Costa Rica Caribbean Holiday

Departure Dec 23, 2025
Duration 12 days
Starting from
$1,948
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⭐ Premium Deals Caribbean
Azamara Cruises
Azamara Onward

14 days, round-trip Cruise Eastern Caribbean Cruise Sint Maarten, Martinique Saint Lucia

Departure Dec 23, 2025
Duration 14 days
Starting from
$3,039
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⭐ Premium Deals
Silversea Cruises
Silver Spirit

14 days, round-trip Bridgetown To Bridgetown

Departure Dec 22, 2025
Duration 14 days
Starting from
$6,700
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⭐ Premium Deals Caribbean
Princess Cruises
Coral Princess

14 days, round-trip Circle Caribbean Holiday

Departure Dec 22, 2025
Duration 14 days
Starting from
$2,248
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Seaside

10 days, round-trip Caribbean Bahamas

Departure Dec 26, 2025
Duration 10 days
Starting from
$1,220
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Legend

10 days, round-trip Western Caribbean

Departure Dec 26, 2025
Duration 10 days
Starting from
$1,729
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from La Romana

Departure Dec 28, 2025
Duration 14 days
Starting from
$1,514
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Explorer Of The Seas

9 days, round-trip Southern Caribbean Holiday

Departure Dec 27, 2025
Duration 9 days
Starting from
$1,631
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Summit

9 days, round-trip Eastern Caribbean Holiday

Departure Dec 27, 2025
Duration 9 days
Starting from
$1,771
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⭐ Premium Deals
Oceania Cruises
Oceania Nautica

9 days, round-trip Jewels of the Yucatan Miami to Miami

Departure Dec 27, 2025
Duration 9 days
Starting from
$1,960
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Freedom Of The Seas

9 days, round-trip Eastern Caribbean Perfect Holiday

Departure Dec 27, 2025
Duration 9 days
Starting from
$1,309
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⭐ Premium Deals
Azamara Cruises
Azamara Quest

10 days, one-way from Bridgetown to Miami

Departure Dec 27, 2025
Duration 10 days
Starting from
$3,179
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Dec 27, 2025
Duration 14 days
Starting from
$2,418
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Dec 28, 2025
Duration 14 days
Starting from
$2,653
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Nieuw Statendam

14 days, round-trip Eastern Caribbean Bahamas San Juan Holiday

Departure Dec 27, 2025
Duration 14 days
Starting from
$1,724
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⭐ Premium Deals Caribbean
Princess Cruises
Enchanted Princess

10 days, round-trip Southern Caribbean with Martinique Holiday

Departure Dec 27, 2025
Duration 10 days
Starting from
$2,098
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 27, 2025
Duration 14 days
Starting from
$2,228
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⭐ Premium Deals Caribbean
Princess Cruises
Sky Princess

14 days, round-trip Eastern Caribbean Adventurer Holiday

Departure Dec 28, 2025
Duration 14 days
Starting from
$1,787
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⭐ Premium Deals
Holland America Cruises
ms Rotterdam

12 days, round-trip Panama Canal Holiday Costa Rica Greater Antilles

Departure Dec 28, 2025
Duration 12 days
Starting from
$1,599
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 28, 2025
Duration 14 days
Starting from
$2,198
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⭐ Premium Deals
Viking Cruises
Viking Sea

10 days, round-trip West Indies Explorer

Departure Dec 29, 2025
Duration 10 days
Starting from
$5,399
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⭐ Premium Deals
Oceania Cruises
Oceania Insignia

10 days, round-trip Maya Isle Mementos Miami to Miami

Departure Dec 29, 2025
Duration 10 days
Starting from
$2,480
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Elizabeth

9 days, round-trip Western Caribbean

Departure Dec 30, 2025
Duration 9 days
Starting from
$1,229
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 28, 2025
Duration 14 days
Starting from
$1,999
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Eurodam

14 days, round-trip WesternEastern Caribbean Bahamas San Juan Holiday

Departure Dec 28, 2025
Duration 14 days
Starting from
$1,544
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Ascent

10 days, round-trip Ultimate Southern Caribbean

Departure Jan 2, 2026
Duration 10 days
Starting from
$1,778
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⭐ Premium Deals
Seabourn Cruises
Seabourn Ovation

14 days, one-way from Bridgetown to Philipsburg St Maarten

Departure Jan 3, 2026
Duration 14 days
Starting from
$6,969
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Koningsdam

11 days, round-trip Eastern Caribbean Windward Leeward Islands

Departure Jan 3, 2026
Duration 11 days
Starting from
$1,549
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⭐ Premium Deals
Star Clippers Cruises
Star Clipper

14 days, one-way from Panama City to Montego Bay

Departure Jan 3, 2026
Duration 14 days
Starting from
$4,240
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⭐ Premium Deals Mexico
Norwegian Cruise Line Cruises
Norwegian Pearl

11 days, round-trip Panama Canal Mexico, Jamaica Costa Rica

Departure Jan 2, 2026
Duration 11 days
Starting from
$1,329
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⭐ Premium Deals Caribbean
Emerald Cruises
Emerald Azzurra

14 days, round-trip Discover the yachting islands of the Caribbean

Departure Jan 3, 2026
Duration 14 days
Starting from
$9,526
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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Grandeur

12 days, one-way from Miami to Panama City

Departure Jan 3, 2026
Duration 12 days
Starting from
$24,298
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Jan 3, 2026
Duration 14 days
Starting from
$1,593
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Odyssey Of The Seas

11 days, round-trip Eastern Caribbean Cruise

Departure Jan 4, 2026
Duration 11 days
Starting from
$1,212
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⭐ Premium Deals Caribbean
Princess Cruises
Caribbean Princess

12 days, round-trip Panama Canal with Costa Rica Caribbean

Departure Jan 4, 2026
Duration 12 days
Starting from
$1,448
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⭐ Premium Deals
Windstar Cruises
Wind Spirit

10 days, one-way from Bridgetown to Philipsburg St Maarten

Departure Jan 4, 2026
Duration 10 days
Starting from
$3,829
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About These Deals
Prices shown are starting rates per person and subject to availability. Deals are updated weekly. Click "View Deal" to check current pricing and availability on CruiseMapper. Port Side Left is not responsible for price changes or booking terms.