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
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
Marella Cruises
Marella Discovery

7 days, round-trip Tropical Isles

Departure Jan 20, 2026
Duration 7 days
Starting from
$2,054
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⭐ Premium Deals
Princess Cruises
Island Princess

16 days, one-way from Fort Lauderdale to Los Angeles

Departure Jan 24, 2026
Duration 16 days
Starting from
$1,999
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⭐ Premium Deals
Seabourn Cruises
Seabourn Ovation

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

Departure Jan 24, 2026
Duration 7 days
Starting from
$4,079
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Koningsdam

21 days, round-trip Eastern Caribbean Leeward U.S. Virgin Islands

Departure Jan 24, 2026
Duration 21 days
Starting from
$2,799
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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
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cayman Coves Jamaican Waterfalls

Departure Jan 24, 2026
Duration 7 days
Starting from
$2,366
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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
Star Clippers Cruises
Star Flyer

7 days, round-trip Leeward Islands

Departure Jan 24, 2026
Duration 7 days
Starting from
$1,970
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⭐ Premium Deals
Holland America Cruises
ms Zuiderdam

22 days, one-way from Miami to San Diego

Departure Jan 24, 2026
Duration 22 days
Starting from
$2,774
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⭐ Premium Deals
Star Clippers Cruises
Royal Clipper

7 days, round-trip Windward Islands

Departure Jan 24, 2026
Duration 7 days
Starting from
$2,030
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Barbados, Antigua, BVI More

Departure Jan 24, 2026
Duration 7 days
Starting from
$2,786
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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

6 days, one-way from Barbuda Island to San Juan

Departure Jan 24, 2026
Duration 6 days
Starting from
$4,829
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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
Disney Cruise Line Cruises
Disney Magic

4 days, round-trip Western Caribbean Cruise From Galveston With Marvel Day At Sea

Departure Jan 25, 2026
Duration 4 days
Starting from
$1,816
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Jan 25, 2026
Duration 7 days
Starting from
$1,558
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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
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Jan 25, 2026
Duration 7 days
Starting from
$1,228
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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
Marella Cruises
Marella Explorer

7 days, round-trip A Taste Of The Tropics

Departure Jan 25, 2026
Duration 7 days
Starting from
$2,280
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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
Windstar Cruises
Wind Surf

15 days, one-way from Bridgetown to Colon

Departure Jan 25, 2026
Duration 15 days
Starting from
$6,199
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⭐ Premium Deals
Windstar Cruises
Wind Surf

7 days, one-way from Bridgetown to Oranjestad Aruba

Departure Jan 25, 2026
Duration 7 days
Starting from
$3,299
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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

20 days, round-trip An Extended Journey to Delightful Island Towns and Tropical Treasures

Departure Jan 25, 2026
Duration 20 days
Starting from
$10,530
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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
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Riviera Maya

Departure Jan 25, 2026
Duration 5 days
Starting from
$1,490
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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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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Grandeur

16 days, one-way from Los Angeles to Miami

Departure Jan 25, 2026
Duration 16 days
Starting from
$28,998
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⭐ Premium Deals
Celebrity Cruises
Celebrity Xcel

7 days, round-trip Puerto Plata, St. Thomas St. Maarten

Departure Jan 25, 2026
Duration 7 days
Starting from
$1,143
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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.