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 Bahamas
Holland America Cruises
ms Nieuw Statendam

14 days, round-trip Western Eastern Caribbean Mexico Bahamas

Departure Nov 29, 2025
Duration 14 days
Starting from
$1,189
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Venezia

14 days, round-trip Southern Caribbean

Departure Nov 30, 2025
Duration 14 days
Starting from
$1,464
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⭐ Premium Deals Caribbean
Princess Cruises
Sky Princess

14 days, round-trip Eastern Caribbean Adventurer

Departure Nov 30, 2025
Duration 14 days
Starting from
$1,668
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Nov 30, 2025
Duration 14 days
Starting from
$1,528
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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Splendor

14 days, one-way from Bridgetown to Rio de Janeiro

Departure Dec 3, 2025
Duration 14 days
Starting from
$25,198
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⭐ Premium Deals Caribbean
Princess Cruises
Enchanted Princess

14 days, round-trip Circle Caribbean

Departure Dec 3, 2025
Duration 14 days
Starting from
$1,808
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⭐ Premium Deals
Viking Cruises
Viking Sky

14 days, one-way from Barcelona to Fort Lauderdale

Departure Dec 5, 2025
Duration 14 days
Starting from
$3,299
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⭐ Premium Deals
Seabourn Cruises
Seabourn Encore

10 days, one-way from Miami to Panama City

Departure Dec 2, 2025
Duration 10 days
Starting from
$5,702
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⭐ Premium Deals
Seabourn Cruises
Seabourn Ovation

12 days, round-trip Treasures Of Aruba, Bonaire Curacao

Departure Dec 2, 2025
Duration 12 days
Starting from
$5,881
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⭐ Premium Deals
Silversea Cruises
Silver Ray

10 days, round-trip FortnbspLauderdale, Florida To FortnbspLauderdale, Florida

Departure Dec 2, 2025
Duration 10 days
Starting from
$5,550
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⭐ Premium Deals Mexico
Norwegian Cruise Line Cruises
Norwegian Jewel

11 days, round-trip Panama Canal Mexico, Costa Rica Belize

Departure Dec 1, 2025
Duration 11 days
Starting from
$1,169
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⭐ Premium Deals
Silversea Cruises
Silver Shadow

9 days, one-way from Cartagena Colombia to Bridgetown

Departure Dec 1, 2025
Duration 9 days
Starting from
$3,400
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Ascent

11 days, round-trip Best of Southern Caribbean

Departure Dec 1, 2025
Duration 11 days
Starting from
$1,815
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⭐ Premium Deals
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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💎 Mid-Range Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Getaway

10 days, round-trip Caribbean Dominican Republic Antigua

Departure Dec 1, 2025
Duration 10 days
Starting from
$987
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⭐ Premium Deals Caribbean
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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⭐ Premium Deals
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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⭐ Premium Deals Caribbean
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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⭐ Premium Deals Caribbean
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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💎 Mid-Range Deals Bahamas
MSC Cruises
MSC Grandiosa

14 days, round-trip Caribbean Bahamas

Departure Dec 6, 2025
Duration 14 days
Starting from
$794
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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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⭐ Premium Deals Caribbean
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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⭐ Premium Deals Caribbean
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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💎 Mid-Range Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Star

10 days, round-trip Caribbean Aruba Dominican Republic

Departure Dec 5, 2025
Duration 10 days
Starting from
$898
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⭐ Premium Deals
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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⭐ Premium Deals
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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💎 Mid-Range Deals Bahamas
MSC Cruises
MSC Divina

11 days, round-trip Caribbean Bahamas

Departure Dec 7, 2025
Duration 11 days
Starting from
$841
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⭐ Premium Deals
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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⭐ Premium Deals
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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⭐ Premium Deals Caribbean
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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⭐ Premium Deals
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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⭐ Premium Deals Caribbean
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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⭐ Premium Deals Caribbean
Princess Cruises
Coral Princess

14 days, round-trip Circle Caribbean Holiday

Departure Dec 8, 2025
Duration 14 days
Starting from
$1,328
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💎 Mid-Range Deals
Cunard Cruises
Queen Elizabeth

9 days, round-trip 185th Anniversary Celebration

Departure Dec 9, 2025
Duration 9 days
Starting from
$869
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Pearl

11 days, round-trip Caribbean Curacao, Aruba Dominican Republic

Departure Dec 8, 2025
Duration 11 days
Starting from
$1,019
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⭐ Premium Deals
Silversea Cruises
Silver Dawn

14 days, one-way from Lisbon to Fort Lauderdale

Departure Dec 8, 2025
Duration 14 days
Starting from
$3,750
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⭐ Premium Deals Caribbean
Oceania Cruises
Oceania Insignia

12 days, round-trip Sunkissed Caribbean Shores Miami to Miami

Departure Dec 7, 2025
Duration 12 days
Starting from
$2,499
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Eurodam

14 days, round-trip Eastern Caribbean Bahamas San Juan

Departure Dec 7, 2025
Duration 14 days
Starting from
$1,174
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⭐ Premium Deals Caribbean
Windstar Cruises
Wind Surf

14 days, round-trip Star Collector Caribbean Explorations

Departure Dec 7, 2025
Duration 14 days
Starting from
$4,199
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

11 days, round-trip Aruban Sunsets Calm Cayman Days

Departure Dec 7, 2025
Duration 11 days
Starting from
$2,840
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⭐ Premium Deals
Holland America Cruises
ms Rotterdam

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

Departure Dec 7, 2025
Duration 12 days
Starting from
$1,199
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 7, 2025
Duration 14 days
Starting from
$1,538
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⭐ Premium Deals
Silversea Cruises
Silver Ray

11 days, round-trip FortnbspLauderdale, Florida To FortnbspLauderdale, Florida

Departure Dec 12, 2025
Duration 11 days
Starting from
$5,100
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⭐ Premium Deals Mexico
Norwegian Cruise Line Cruises
Norwegian Jewel

11 days, round-trip Panama Canal Mexico, Costa Rica Belize

Departure Dec 12, 2025
Duration 11 days
Starting from
$1,159
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💎 Mid-Range Deals Caribbean
Princess Cruises
Caribbean Princess

12 days, round-trip Circle Caribbean

Departure Dec 11, 2025
Duration 12 days
Starting from
$798
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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Grandeur

11 days, round-trip Rhythm Of Paradise Miami To Miami

Departure Dec 11, 2025
Duration 11 days
Starting from
$18,398
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⭐ Premium Deals Caribbean
Azamara Cruises
Azamara Quest

14 days, round-trip Cruise Eastern Caribbean Cruise San Juan, St. Johns Bridgetown

Departure Dec 13, 2025
Duration 14 days
Starting from
$3,559
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Koningsdam

11 days, round-trip Eastern Caribbean Windward Leeward Islands

Departure Dec 9, 2025
Duration 11 days
Starting from
$1,199
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⭐ Premium Deals
Silversea Cruises
Silver Shadow

9 days, one-way from Bridgetown to Cartagena Colombia

Departure Dec 10, 2025
Duration 9 days
Starting from
$2,800
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⭐ Premium Deals
Regent Seven Seas Cruises
Seven Seas Mariner

10 days, round-trip Passage To Paradise Miami To Miami

Departure Dec 10, 2025
Duration 10 days
Starting from
$17,398
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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.