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
Seabourn Cruises
Seabourn Ovation

14 days, round-trip Gems Of The Caribbean

Departure Jan 17, 2026
Duration 14 days
Starting from
$7,564
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Jan 17, 2026
Duration 14 days
Starting from
$2,286
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 17, 2026
Duration 14 days
Starting from
$1,518
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from La Romana

Departure Jan 18, 2026
Duration 14 days
Starting from
$1,708
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Dream

14 days, round-trip Eastern Caribbean

Departure Jan 18, 2026
Duration 14 days
Starting from
$1,709
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⭐ Premium Deals
Windstar Cruises
Wind Surf

14 days, one-way from Bridgetown to Oranjestad Aruba

Departure Jan 18, 2026
Duration 14 days
Starting from
$6,099
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⭐ Premium Deals
Holland America Cruises
ms Rotterdam

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

Departure Jan 18, 2026
Duration 12 days
Starting from
$1,399
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 18, 2026
Duration 14 days
Starting from
$1,478
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Vision Of The Seas

12 days, round-trip Southern Caribbean Cruise

Departure Jan 24, 2026
Duration 12 days
Starting from
$1,189
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Ascent

10 days, round-trip Ultimate Southern Caribbean

Departure Jan 23, 2026
Duration 10 days
Starting from
$1,788
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⭐ Premium Deals
Windstar Cruises
Star Seeker

14 days, round-trip Star Collector Lovely Leewards

Departure Jan 23, 2026
Duration 14 days
Starting from
$17,199
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from Guadeloupe

Departure Jan 22, 2026
Duration 14 days
Starting from
$1,752
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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 19, 2026
Duration 11 days
Starting from
$1,259
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⭐ Premium Deals Caribbean
Princess Cruises
Sky Princess

14 days, round-trip Eastern Caribbean Adventurer

Departure Jan 19, 2026
Duration 14 days
Starting from
$1,447
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

14 days, round-trip An Extended Journey between Sophistication Silky Sands

Departure Jan 19, 2026
Duration 14 days
Starting from
$7,785
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Getaway

10 days, round-trip Caribbean Dominican Republic Antigua

Departure Jan 19, 2026
Duration 10 days
Starting from
$1,069
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⭐ Premium Deals Caribbean
Seabourn Cruises
Seabourn Ovation

14 days, round-trip Exotic Caribbean Isles

Departure Jan 24, 2026
Duration 14 days
Starting from
$7,394
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Jan 24, 2026
Duration 14 days
Starting from
$2,062
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 24, 2026
Duration 14 days
Starting from
$1,458
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Koningsdam

11 days, round-trip Eastern Caribbean Windward Leeward Islands

Departure Jan 24, 2026
Duration 11 days
Starting from
$1,599
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⭐ Premium Deals
Emerald Cruises
Emerald Azzurra

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

Departure Jan 24, 2026
Duration 12 days
Starting from
$9,526
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Viva

14 days, round-trip Caribbean Cozumel Dominican Republic

Departure Jan 24, 2026
Duration 14 days
Starting from
$1,889
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Jan 25, 2026
Duration 14 days
Starting from
$1,370
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⭐ Premium Deals Caribbean
Princess Cruises
Sky Princess

14 days, round-trip Eastern Caribbean Adventurer

Departure Jan 25, 2026
Duration 14 days
Starting from
$1,499
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⭐ Premium Deals
Silversea Cruises
Silver Shadow

9 days, one-way from Bridgetown to Cartagena Colombia

Departure Jan 25, 2026
Duration 9 days
Starting from
$6,300
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 2

10 days, round-trip A Journey of Dutch Delights in the ABC Islands

Departure Jan 25, 2026
Duration 10 days
Starting from
$5,605
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Divina

13 days, round-trip Caribbean Bahamas

Departure Jan 25, 2026
Duration 13 days
Starting from
$1,057
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from La Romana

Departure Jan 25, 2026
Duration 14 days
Starting from
$1,709
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 25, 2026
Duration 14 days
Starting from
$1,478
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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.