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
Azamara Cruises
Azamara Quest

14 days, one-way from Montreal to Miami

Departure Oct 17, 2025
Duration 14 days
Starting from
$2,309
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Royal Caribbean Cruises
Independence Of The Seas

14 days, one-way from Southampton to Miami

Departure Oct 16, 2025
Duration 14 days
Starting from
$1,268
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Elizabeth

12 days, round-trip Eastern Caribbean

Departure Oct 16, 2025
Duration 12 days
Starting from
$1,299
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⭐ Premium Deals Caribbean
Princess Cruises
Caribbean Princess

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

Departure Oct 16, 2025
Duration 12 days
Starting from
$1,229
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Princess Cruises
Star Princess

14 days, one-way from Barcelona to Fort Lauderdale

Departure Oct 22, 2025
Duration 14 days
Starting from
$1,819
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Celebrity Cruises
Celebrity Apex

13 days, one-way from Southampton to Port Canaveral

Departure Oct 19, 2025
Duration 13 days
Starting from
$1,506
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Holland America Cruises
ms Zuiderdam

14 days, one-way from Boston to Miami

Departure Oct 18, 2025
Duration 14 days
Starting from
$1,199
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Dream

14 days, round-trip Eastern Caribbean

Departure Oct 18, 2025
Duration 14 days
Starting from
$1,734
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Reflection

11 days, round-trip Southern Caribbean

Departure Oct 18, 2025
Duration 11 days
Starting from
$1,296
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Oct 18, 2025
Duration 14 days
Starting from
$2,138
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⭐ Premium Deals
Princess Cruises
Majestic Princess

14 days, one-way from Quebec City to Fort Lauderdale

Departure Oct 19, 2025
Duration 14 days
Starting from
$1,469
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Oct 19, 2025
Duration 14 days
Starting from
$1,437
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Oct 25, 2025
Duration 14 days
Starting from
$2,315
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⭐ Premium Deals
Royal Caribbean Cruises
Allure Of The Seas

13 days, one-way from Barcelona to Fort Lauderdale

Departure Oct 26, 2025
Duration 13 days
Starting from
$1,223
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⭐ Premium Deals
Hapag-Lloyd Cruises
Hanseatic Inspiration

14 days, one-way from Halifax to Panama City

Departure Oct 25, 2025
Duration 14 days
Starting from
$5,797
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Oct 26, 2025
Duration 14 days
Starting from
$1,307
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

14 days, one-way from Barcelona to Miami

Departure Oct 26, 2025
Duration 14 days
Starting from
$3,080
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⭐ Premium Deals
Holland America Cruises
ms Rotterdam

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

Departure Oct 26, 2025
Duration 12 days
Starting from
$1,099
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⭐ Premium Deals
Celebrity Cruises
Celebrity Eclipse

13 days, one-way from Barcelona to Fort Lauderdale

Departure Oct 30, 2025
Duration 13 days
Starting from
$1,178
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

13 days, one-way from Barcelona to San Juan

Departure Oct 27, 2025
Duration 13 days
Starting from
$5,235
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⭐ Premium Deals Caribbean
Princess Cruises
Caribbean Princess

10 days, round-trip Southern Caribbean with Martinique

Departure Oct 28, 2025
Duration 10 days
Starting from
$1,193
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Mardi Gras

9 days, round-trip Eastern Caribbean

Departure Oct 30, 2025
Duration 9 days
Starting from
$1,249
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⭐ Premium Deals
Celebrity Cruises
Celebrity Ascent

13 days, one-way from Civitavecchia-Rome to Fort Lauderdale

Departure Oct 31, 2025
Duration 13 days
Starting from
$1,003
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Legend

10 days, round-trip Caribbean Panama

Departure Oct 27, 2025
Duration 10 days
Starting from
$1,489
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Nov 2, 2025
Duration 14 days
Starting from
$1,934
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Pride

14 days, round-trip Southern Caribbean

Departure Nov 2, 2025
Duration 14 days
Starting from
$1,819
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Windstar Cruises
Star Pride

14 days, round-trip Star Collector Lovely Leewards

Departure Nov 2, 2025
Duration 14 days
Starting from
$5,469
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Nov 2, 2025
Duration 14 days
Starting from
$1,427
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⭐ Premium Deals
Oceania Cruises
Oceania Regatta

12 days, one-way from Los Angeles to Colon

Departure Nov 2, 2025
Duration 12 days
Starting from
$2,405
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⭐ Premium Deals
Seabourn Cruises
Seabourn Sojourn

10 days, one-way from Montreal to Miami

Departure Nov 1, 2025
Duration 10 days
Starting from
$3,998
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Vision Of The Seas

12 days, round-trip Southern Caribbean Cruise

Departure Nov 1, 2025
Duration 12 days
Starting from
$1,158
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Zuiderdam

14 days, round-trip Eastern Western Caribbean San Juan Mexico

Departure Nov 1, 2025
Duration 14 days
Starting from
$1,229
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⭐ Premium Deals
Star Clippers Cruises
Royal Clipper

14 days, one-way from Bridgetown to Panama City

Departure Nov 1, 2025
Duration 14 days
Starting from
$4,350
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⭐ Premium Deals Bahamas
MSC Cruises
MSC World America

14 days, round-trip Caribbean Bahamas

Departure Nov 1, 2025
Duration 14 days
Starting from
$1,472
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⭐ Premium Deals
Hapag-Lloyd Cruises
Hanseatic Inspiration

11 days, one-way from Panama City to Colon Cristobal Pier

Departure Nov 8, 2025
Duration 11 days
Starting from
$7,424
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Fantasy

13 days, one-way from Southampton to Port Canaveral

Departure Nov 3, 2025
Duration 13 days
Starting from
$4,196
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⭐ Premium Deals
Windstar Cruises
Wind Spirit

14 days, one-way from Lisbon to Bridgetown

Departure Nov 4, 2025
Duration 14 days
Starting from
$2,999
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Odyssey Of The Seas

11 days, round-trip Eastern Caribbean Cruise

Departure Nov 5, 2025
Duration 11 days
Starting from
$1,537
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Elizabeth

12 days, round-trip Eastern Caribbean

Departure Nov 6, 2025
Duration 12 days
Starting from
$1,299
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Divina

14 days, round-trip Caribbean Bahamas

Departure Nov 6, 2025
Duration 14 days
Starting from
$2,297
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⭐ Premium Deals Caribbean
Princess Cruises
Caribbean Princess

10 days, round-trip Eastern Caribbean with Tortola

Departure Nov 7, 2025
Duration 10 days
Starting from
$1,128
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⭐ Premium Deals Caribbean
Princess Cruises
Island Princess

14 days, round-trip Circle Caribbean

Departure Nov 7, 2025
Duration 14 days
Starting from
$1,484
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Nov 9, 2025
Duration 14 days
Starting from
$1,657
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⭐ Premium Deals
Marella Cruises
Marella Explorer

14 days, one-way from Malaga to Bridgetown

Departure Nov 9, 2025
Duration 14 days
Starting from
$2,018
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Summit

10 days, round-trip Eastern Caribbean

Departure Nov 10, 2025
Duration 10 days
Starting from
$1,099
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Legend

10 days, round-trip Eastern Caribbean

Departure Nov 10, 2025
Duration 10 days
Starting from
$1,324
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

12 days, round-trip Colorful Curaccedilao to the Charming Caymans

Departure Nov 8, 2025
Duration 12 days
Starting from
$3,576
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Nov 8, 2025
Duration 14 days
Starting from
$2,195
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⭐ Premium Deals Caribbean
Azamara Cruises
Azamara Quest

14 days, round-trip Eastern Caribbean Voyage

Departure Nov 8, 2025
Duration 14 days
Starting from
$4,579
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⭐ Premium Deals
Crystal Cruises
Crystal Serenity

12 days, one-way from New York to Bridgetown

Departure Nov 8, 2025
Duration 12 days
Starting from
$4,800
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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.