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 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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⭐ 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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⭐ Premium Deals Caribbean
Azamara Cruises
Azamara Onward

11 days, round-trip Cruise Eastern Caribbean Cruise St. Thomas, Sint Maarten British Virgin Islands

Departure Dec 12, 2025
Duration 11 days
Starting from
$1,789
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

9 days, one-way from Miami to Bridgetown

Departure Dec 12, 2025
Duration 9 days
Starting from
$3,975
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Ascent

10 days, round-trip Ultimate Southern Caribbean

Departure Dec 12, 2025
Duration 10 days
Starting from
$5,688
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 14, 2025
Duration 14 days
Starting from
$1,499
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Nieuw Statendam

14 days, round-trip EasternWestern Caribbean San Juan Mexico Holiday

Departure Dec 13, 2025
Duration 14 days
Starting from
$1,424
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Grandiosa

14 days, round-trip Caribbean Bahamas

Departure Dec 13, 2025
Duration 14 days
Starting from
$1,077
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⭐ Premium Deals
Emerald Cruises
Emerald Azzurra

12 days, one-way from Barbuda Island to Montserrat Island UK

Departure Dec 13, 2025
Duration 12 days
Starting from
$8,945
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 13, 2025
Duration 14 days
Starting from
$1,788
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Dec 13, 2025
Duration 14 days
Starting from
$1,591
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⭐ Premium Deals
Emerald Cruises
Emerald Sakara

14 days, one-way from Bridgetown to Marigot

Departure Dec 13, 2025
Duration 14 days
Starting from
$9,382
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Dec 14, 2025
Duration 14 days
Starting from
$1,729
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Eurodam

14 days, round-trip Eastern Caribbean Bahamas San Juan Holiday

Departure Dec 14, 2025
Duration 14 days
Starting from
$1,384
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⭐ Premium Deals Caribbean
Windstar Cruises
Wind Surf

14 days, round-trip Star Collector Caribbean Explorations

Departure Dec 14, 2025
Duration 14 days
Starting from
$4,899
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Seashore

10 days, round-trip Caribbean Bahamas

Departure Dec 18, 2025
Duration 10 days
Starting from
$1,089
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⭐ Premium Deals Bahamas
MSC Cruises
MSC Seaside

14 days, round-trip Caribbean Bahamas

Departure Dec 19, 2025
Duration 14 days
Starting from
$1,570
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 14, 2025
Duration 14 days
Starting from
$1,808
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⭐ Premium Deals Caribbean
Princess Cruises
Enchanted Princess

10 days, round-trip Southern Caribbean with St. Kitts Holiday

Departure Dec 17, 2025
Duration 10 days
Starting from
$1,038
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⭐ Premium Deals Caribbean
Oceania Cruises
Oceania Nautica

10 days, round-trip Caribbean Elegance Miami to Miami

Departure Dec 17, 2025
Duration 10 days
Starting from
$2,100
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Summit

9 days, round-trip Eastern Caribbean Holiday

Departure Dec 18, 2025
Duration 9 days
Starting from
$1,126
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Elizabeth

12 days, round-trip Eastern Caribbean Celebration

Departure Dec 18, 2025
Duration 12 days
Starting from
$1,499
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Rotterdam

9 days, round-trip Southern Caribbean Holiday Abc Islands

Departure Dec 19, 2025
Duration 9 days
Starting from
$1,199
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⭐ Premium Deals
Silversea Cruises
Silver Shadow

9 days, one-way from Cartagena Colombia to Bridgetown

Departure Dec 19, 2025
Duration 9 days
Starting from
$3,450
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⭐ Premium Deals
Oceania Cruises
Oceania Insignia

10 days, round-trip Yachting Treasures Miami to Miami

Departure Dec 19, 2025
Duration 10 days
Starting from
$2,400
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 20, 2025
Duration 14 days
Starting from
$2,179
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⭐ Premium Deals Caribbean
Regent Seven Seas Cruises
Seven Seas Mariner

14 days, round-trip Caribbean Quest Miami To Miami

Departure Dec 20, 2025
Duration 14 days
Starting from
$22,598
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Koningsdam

14 days, round-trip Eastern Caribbean Bahamas San Juan Holiday

Departure Dec 20, 2025
Duration 14 days
Starting from
$2,119
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⭐ Premium Deals Bahamas
Holland America Cruises
ms Nieuw Statendam

14 days, round-trip Western Eastern Caribbean Mexico Bahamas Holiday

Departure Dec 20, 2025
Duration 14 days
Starting from
$1,889
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer Holiday

Departure Dec 20, 2025
Duration 14 days
Starting from
$2,478
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Dec 21, 2025
Duration 14 days
Starting from
$3,079
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from La Romana

Departure Dec 21, 2025
Duration 14 days
Starting from
$2,088
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Mary 2

12 days, round-trip Caribbean Celebration

Departure Dec 22, 2025
Duration 12 days
Starting from
$2,499
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⭐ Premium Deals
Silversea Cruises
Silver Dawn

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

Departure Dec 22, 2025
Duration 14 days
Starting from
$10,600
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Dec 20, 2025
Duration 14 days
Starting from
$2,657
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Eurodam

14 days, round-trip EasternWestern Caribbean San Juan Mexico Holiday

Departure Dec 21, 2025
Duration 14 days
Starting from
$1,824
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Volendam

14 days, round-trip Eastern Caribbean Antilles Private Island Holiday

Departure Dec 21, 2025
Duration 14 days
Starting from
$1,999
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Dawn

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

Departure Dec 21, 2025
Duration 10 days
Starting from
$1,300
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⭐ Premium Deals Caribbean
Windstar Cruises
Wind Surf

14 days, round-trip Star Collector Caribbean Explorations

Departure Dec 21, 2025
Duration 14 days
Starting from
$5,999
View Deal
⭐ Premium Deals Caribbean
MSC Explora Journeys Cruises
MSC Explora 1

13 days, round-trip An Extended Celebration Journey into New Caribbean Dawns

Departure Dec 21, 2025
Duration 13 days
Starting from
$8,680
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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.