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
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
Royal Caribbean Cruises
Brilliance Of The Seas

7 days, one-way from Boston to San Juan

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,198
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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 Caribbean
Disney Cruise Line Cruises
Disney Treasure

7 days, round-trip Western Caribbean Cruise From Port Canaveral

Departure Nov 1, 2025
Duration 7 days
Starting from
$4,357
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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
Celebrity Cruises
Celebrity Silhouette

8 days, round-trip Aruba, Curacao Bonaire

Departure Nov 1, 2025
Duration 8 days
Starting from
$1,297
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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 Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 1, 2025
Duration 7 days
Starting from
$1,263
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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 Caribbean
Royal Caribbean Cruises
Oasis Of The Seas

8 days, round-trip Southern Caribbean Perfect Day

Departure Nov 1, 2025
Duration 8 days
Starting from
$1,104
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⭐ Premium Deals
Holland America Cruises
ms Koningsdam

28 days, one-way from San Diego to Fort Lauderdale

Departure Nov 1, 2025
Duration 28 days
Starting from
$2,554
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⭐ Premium Deals
Holland America Cruises
ms Koningsdam

17 days, one-way from San Diego to Fort Lauderdale

Departure Nov 1, 2025
Duration 17 days
Starting from
$1,399
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⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Brilliant Lady

7 days, round-trip Western Caribbean From Miami to Bimini

Departure Nov 1, 2025
Duration 7 days
Starting from
$2,226
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⭐ Premium Deals
Princess Cruises
Sun Princess

15 days, one-way from Barcelona to Fort Lauderdale

Departure Nov 1, 2025
Duration 15 days
Starting from
$1,019
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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 Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,681
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⭐ Premium Deals
Lindblad Expeditions Cruises
National Geographic Quest

7 days, one-way from Panama City to Cartagena Colombia

Departure Nov 2, 2025
Duration 7 days
Starting from
$6,741
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

6 days, one-way from Miami to San Juan

Departure Nov 2, 2025
Duration 6 days
Starting from
$1,428
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⭐ Premium Deals Caribbean
Margaritaville at Sea Cruises
Margaritaville Islander

7 days, round-trip Mexico Western Caribbean

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,525
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,461
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⭐ Premium Deals
Holland America Cruises
ms Oosterdam

15 days, one-way from Barcelona to Fort Lauderdale

Departure Nov 2, 2025
Duration 15 days
Starting from
$1,209
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⭐ Premium Deals
Silversea Cruises
Silver Ray

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

Departure Nov 7, 2025
Duration 25 days
Starting from
$11,500
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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 Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 8, 2025
Duration 7 days
Starting from
$1,307
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Dream

4 days, round-trip Bahamian Cruise From Fort Lauderdale

Departure Nov 8, 2025
Duration 4 days
Starting from
$1,767
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

7 days, round-trip Very Merrytime Eastern Caribbean Cruise From Port Canaveral

Departure Nov 8, 2025
Duration 7 days
Starting from
$5,475
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Allure Of The Seas

8 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 8, 2025
Duration 8 days
Starting from
$1,042
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Wish

4 days, round-trip Bahamian Cruise From Port Canaveral

Departure Nov 3, 2025
Duration 4 days
Starting from
$2,275
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Dream

5 days, round-trip Bahamian Cruise From Fort Lauderdale

Departure Nov 3, 2025
Duration 5 days
Starting from
$2,251
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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
Windstar Cruises
Wind Spirit

25 days, one-way from Lisbon to Colon

Departure Nov 4, 2025
Duration 25 days
Starting from
$6,399
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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
Star Clippers Cruises
Star Clipper

24 days, one-way from Malaga to Bridgetown

Departure Nov 5, 2025
Duration 24 days
Starting from
$4,610
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⭐ Premium Deals
Azamara Cruises
Azamara Onward

24 days, one-way from Barcelona to Miami

Departure Nov 6, 2025
Duration 24 days
Starting from
$6,689
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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
Cunard Cruises
Queen Elizabeth

21 days, round-trip Caribbean

Departure Nov 6, 2025
Duration 21 days
Starting from
$2,114
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Wish

3 days, round-trip Very Merrytime Bahamian Cruise From Port Canaveral

Departure Nov 7, 2025
Duration 3 days
Starting from
$2,528
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Magic

7 days, round-trip Southern Caribbean Cruise From San Juan

Departure Nov 7, 2025
Duration 7 days
Starting from
$2,676
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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
Star Clippers Cruises
Star Flyer

15 days, one-way from Las Palmas de Gran Canaria to Philipsburg St Maarten

Departure Nov 7, 2025
Duration 15 days
Starting from
$2,850
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Rotterdam

21 days, round-trip Southern Eastern Caribbean Abc Islands

Departure Nov 7, 2025
Duration 21 days
Starting from
$2,119
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Dominican Daze

Departure Nov 7, 2025
Duration 5 days
Starting from
$1,792
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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 Caribbean
Virgin Voyages Cruises
Resilient Lady

6 days, round-trip Western Caribbean Charm

Departure Nov 9, 2025
Duration 6 days
Starting from
$1,298
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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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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.