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
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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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from La Romana

Departure Jan 4, 2026
Duration 14 days
Starting from
$1,784
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

11 days, round-trip Aruba, Bonaire, Colombia, Jamaica More

Departure Jan 4, 2026
Duration 11 days
Starting from
$3,632
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Jan 4, 2026
Duration 14 days
Starting from
$1,393
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⭐ Premium Deals Mexico
Norwegian Cruise Line Cruises
Norwegian Jewel

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

Departure Jan 4, 2026
Duration 11 days
Starting from
$1,179
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Dream

14 days, round-trip Caribbean Panama

Departure Jan 4, 2026
Duration 14 days
Starting from
$1,654
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Sky

9 days, round-trip Caribbean Aruba Barbados

Departure Jan 5, 2026
Duration 9 days
Starting from
$1,209
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⭐ Premium Deals
Windstar Cruises
Wind Surf

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

Departure Jan 4, 2026
Duration 14 days
Starting from
$5,399
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 4, 2026
Duration 14 days
Starting from
$1,518
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⭐ Premium Deals Caribbean
Oceania Cruises
Oceania Nautica

12 days, round-trip Azure Caribbean Miami to Miami

Departure Jan 5, 2026
Duration 12 days
Starting from
$3,499
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⭐ Premium Deals
Silversea Cruises
Silver Spirit

11 days, one-way from Bridgetown to Fort Lauderdale

Departure Jan 5, 2026
Duration 11 days
Starting from
$7,400
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from Guadeloupe

Departure Jan 8, 2026
Duration 14 days
Starting from
$1,751
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Elizabeth

12 days, round-trip Eastern Caribbean

Departure Jan 8, 2026
Duration 12 days
Starting from
$1,599
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⭐ Premium Deals
Silversea Cruises
Silver Ray

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

Departure Jan 6, 2026
Duration 10 days
Starting from
$7,800
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⭐ Premium Deals Caribbean
Princess Cruises
Enchanted Princess

10 days, round-trip Eastern Caribbean with St. Kitts

Departure Jan 6, 2026
Duration 10 days
Starting from
$1,498
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 2

10 days, round-trip A Journey to the Land Bridge Connecting the Americas

Departure Jan 5, 2026
Duration 10 days
Starting from
$6,165
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Getaway

10 days, round-trip Caribbean Dominican Republic Antigua

Departure Jan 5, 2026
Duration 10 days
Starting from
$1,049
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⭐ Premium Deals
Silversea Cruises
Silver Dawn

13 days, one-way from Fort Lauderdale to Callao-Lima

Departure Jan 6, 2026
Duration 13 days
Starting from
$11,100
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⭐ Premium Deals
Azamara Cruises
Azamara Quest

11 days, one-way from Miami to Bridgetown

Departure Jan 6, 2026
Duration 11 days
Starting from
$3,329
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Rotterdam

9 days, round-trip Southern Caribbean Abc Islands With History Channel

Departure Jan 9, 2026
Duration 9 days
Starting from
$1,199
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Jan 11, 2026
Duration 14 days
Starting from
$1,249
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Pride

14 days, round-trip Caribbean Panama

Departure Jan 11, 2026
Duration 14 days
Starting from
$4,190
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⭐ Premium Deals Caribbean
Seabourn Cruises
Seabourn Ovation

14 days, round-trip Exotic Caribbean Isles

Departure Jan 10, 2026
Duration 14 days
Starting from
$7,649
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⭐ Premium Deals
Emerald Cruises
Emerald Azzurra

12 days, one-way from Barbuda Island to Montserrat Island UK

Departure Jan 10, 2026
Duration 12 days
Starting from
$9,526
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 10, 2026
Duration 14 days
Starting from
$1,598
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Jan 10, 2026
Duration 14 days
Starting from
$2,359
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Viva

14 days, round-trip Caribbean Cozumel Dominican Republic

Departure Jan 10, 2026
Duration 14 days
Starting from
$1,919
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

14 days, round-trip SouthernEastern Caribbean Adventurer

Departure Jan 11, 2026
Duration 14 days
Starting from
$2,160
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from La Romana

Departure Jan 11, 2026
Duration 14 days
Starting from
$1,708
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 11, 2026
Duration 14 days
Starting from
$1,458
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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.