Caribbean Cruise Deals

Discover amazing cruise deals departing in the next 6 months. Updated weekly with the latest prices from major cruise lines!

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Regent Seven Seas Cruises
Seven Seas Grandeur

10 days, round-trip Island Adventures Miami To Miami

Departure Dec 1, 2025
Duration 10 days
Starting from
$18,798
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Oceania Cruises
Oceania Nautica

25 days, one-way from Barcelona to Miami

Departure Dec 2, 2025
Duration 25 days
Starting from
$5,599
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Oceania Cruises
Oceania Nautica

15 days, one-way from Barcelona to Miami

Departure Dec 2, 2025
Duration 15 days
Starting from
$2,799
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Windstar Cruises
Wind Surf

12 days, round-trip Star Collector Ivory Beaches Sapphire Seas of the Caribbean

Departure Dec 2, 2025
Duration 12 days
Starting from
$3,483
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Marella Cruises
Marella Discovery

14 days, one-way from Vigo to La Romana

Departure Dec 2, 2025
Duration 14 days
Starting from
$2,196
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Windstar Cruises
Wind Surf

5 days, round-trip Barefoot Break in the British Virgin Islands

Departure Dec 2, 2025
Duration 5 days
Starting from
$2,399
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Princess Cruises
Majestic Princess

8 days, round-trip Southern Caribbean with ABC Islands

Departure Dec 6, 2025
Duration 8 days
Starting from
$1,058
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Costa Cruises
Costa Pacifica

15 days, one-way from Savona to La Romana

Departure Dec 6, 2025
Duration 15 days
Starting from
$1,669
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Costa Cruises
Costa Pacifica

22 days, one-way from Savona to La Romana

Departure Dec 6, 2025
Duration 22 days
Starting from
$1,827
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Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Dec 6, 2025
Duration 14 days
Starting from
$1,625
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Costa Cruises
Costa Pacifica

19 days, one-way from Savona to Pointe-a-Pitre

Departure Dec 6, 2025
Duration 19 days
Starting from
$1,541
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Royal Caribbean Cruises
Adventure Of The Seas

6 days, round-trip Western Caribbean Cruise

Departure Dec 6, 2025
Duration 6 days
Starting from
$1,077
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Star Clippers Cruises
Star Flyer

7 days, round-trip Treasure Islands

Departure Dec 6, 2025
Duration 7 days
Starting from
$1,970
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Star Clippers Cruises
Royal Clipper

7 days, round-trip Grenadine Islands

Departure Dec 6, 2025
Duration 7 days
Starting from
$2,030
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Holland America Cruises
ms Zuiderdam

17 days, round-trip Eastern Southern Caribbean San Juan Abc Islands

Departure Dec 6, 2025
Duration 17 days
Starting from
$1,409
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Norwegian Cruise Line Cruises
Norwegian Sky

16 days, one-way from Barcelona to La Romana

Departure Dec 6, 2025
Duration 16 days
Starting from
$1,149
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Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Dec 6, 2025
Duration 7 days
Starting from
$1,519
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MSC Cruises
MSC Virtuosa

7 days, round-trip Southern Caribbean

Departure Dec 6, 2025
Duration 7 days
Starting from
$1,396
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Royal Caribbean Cruises
Allure Of The Seas

8 days, round-trip Eastern Caribbean Perfect Day

Departure Dec 6, 2025
Duration 8 days
Starting from
$1,048
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Windstar Cruises
Wind Spirit

7 days, one-way from Puntarenas to Colon

Departure Dec 6, 2025
Duration 7 days
Starting from
$4,199
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Azamara Cruises
Azamara Quest

7 days, one-way from San Juan to Bridgetown

Departure Dec 6, 2025
Duration 7 days
Starting from
$2,489
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Azamara Cruises
Azamara Quest

13 days, round-trip Eastern Caribbean Voyage

Departure Dec 6, 2025
Duration 13 days
Starting from
$3,369
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Nieuw Statendam

14 days, round-trip Eastern Caribbean Bahamas San Juan

Departure Dec 6, 2025
Duration 14 days
Starting from
$1,284
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Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cayman Coves Jamaican Waterfalls

Departure Dec 6, 2025
Duration 7 days
Starting from
$1,806
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Emerald Cruises
Emerald Sakara

7 days, one-way from Marigot to Bridgetown

Departure Dec 6, 2025
Duration 7 days
Starting from
$6,330
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MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Dec 6, 2025
Duration 14 days
Starting from
$1,372
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Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Dec 6, 2025
Duration 14 days
Starting from
$1,578
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Viking Cruises
Viking Sea

14 days, one-way from Barcelona to San Juan

Departure Dec 5, 2025
Duration 14 days
Starting from
$3,299
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MSC Explora Journeys Cruises
MSC Explora 1

7 days, one-way from San Juan to Miami

Departure Dec 5, 2025
Duration 7 days
Starting from
$4,100
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Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Dominican Daze

Departure Dec 5, 2025
Duration 5 days
Starting from
$1,792
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MSC Explora Journeys Cruises
MSC Explora 1

16 days, one-way from San Juan to Bridgetown

Departure Dec 5, 2025
Duration 16 days
Starting from
$7,080
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MSC Explora Journeys Cruises
MSC Explora 2

17 days, round-trip An Extended Journey of Caribbean Culture Enchanting Islands

Departure Dec 5, 2025
Duration 17 days
Starting from
$9,280
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MSC Explora Journeys Cruises
MSC Explora 2

9 days, one-way from Miami to Bridgetown

Departure Dec 5, 2025
Duration 9 days
Starting from
$4,920
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Disney Cruise Line Cruises
Disney Treasure

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

Departure Dec 6, 2025
Duration 7 days
Starting from
$5,321
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Disney Cruise Line Cruises
Disney Magic

4 days, round-trip Very Merrytime Western Caribbean Cruise From Galveston

Departure Dec 7, 2025
Duration 4 days
Starting from
$2,131
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MSC Cruises
MSC Virtuosa

7 days, round-trip Southern Caribbean

Departure Dec 7, 2025
Duration 7 days
Starting from
$1,757
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Lindblad Expeditions Cruises
National Geographic Quest

7 days, one-way from Colon to Panama City

Departure Dec 7, 2025
Duration 7 days
Starting from
$7,315
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Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Dec 7, 2025
Duration 7 days
Starting from
$1,520
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Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Dec 7, 2025
Duration 7 days
Starting from
$1,621
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Divina

21 days, round-trip Caribbean Bahamas

Departure Dec 7, 2025
Duration 21 days
Starting from
$1,730
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Crystal Cruises
Crystal Serenity

7 days, one-way from Bridgetown to Cartagena Colombia

Departure Dec 7, 2025
Duration 7 days
Starting from
$3,600
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Windstar Cruises
Star Pride

6 days, one-way from San Juan to Colon

Departure Dec 7, 2025
Duration 6 days
Starting from
$2,599
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Costa Cruises
Costa Pacifica

14 days, one-way from Marseille to La Romana

Departure Dec 7, 2025
Duration 14 days
Starting from
$1,209
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Disney Cruise Line Cruises
Disney Fantasy

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

Departure Dec 7, 2025
Duration 5 days
Starting from
$3,817
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Windstar Cruises
Star Pride

13 days, one-way from San Juan to Puntarenas

Departure Dec 7, 2025
Duration 13 days
Starting from
$4,199
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Costa Cruises
Costa Pacifica

21 days, one-way from Marseille to La Romana

Departure Dec 7, 2025
Duration 21 days
Starting from
$2,337
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Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Dec 7, 2025
Duration 14 days
Starting from
$1,203
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Costa Cruises
Costa Pacifica

18 days, one-way from Marseille to Pointe-a-Pitre

Departure Dec 7, 2025
Duration 18 days
Starting from
$1,911
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Costa Cruises
Costa Pacifica

13 days, one-way from Barcelona to La Romana

Departure Dec 8, 2025
Duration 13 days
Starting from
$1,160
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Carnival Cruise Line Cruises
Carnival Legend

10 days, round-trip Caribbean Panama

Departure Dec 8, 2025
Duration 10 days
Starting from
$1,219
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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.