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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Windstar Cruises
Wind Surf

7 days, one-way from Philipsburg St Maarten to Bridgetown

Departure Jan 11, 2026
Duration 7 days
Starting from
$3,199
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Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Riviera Maya

Departure Jan 11, 2026
Duration 5 days
Starting from
$1,490
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Norwegian Cruise Line Cruises
Norwegian Sky

12 days, round-trip Caribbean Curacao, Aruba Barbados

Departure Jan 14, 2026
Duration 12 days
Starting from
$2,039
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Disney Cruise Line Cruises
Disney Fantasy

4 days, round-trip Bahamian Cruise From Port Canaveral

Departure Jan 14, 2026
Duration 4 days
Starting from
$2,141
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Holland America Cruises
ms Koningsdam

21 days, round-trip Western Eastern Caribbean Mexico Leeward Islands

Departure Jan 14, 2026
Duration 21 days
Starting from
$2,609
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Holland America Cruises
ms Koningsdam

10 days, round-trip Western Caribbean Greater Antilles, Belize Mexico

Departure Jan 14, 2026
Duration 10 days
Starting from
$1,349
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Royal Caribbean Cruises
Odyssey Of The Seas

11 days, round-trip Southern Caribbean Cruise

Departure Jan 15, 2026
Duration 11 days
Starting from
$1,334
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Marella Cruises
Marella Discovery 2

7 days, round-trip Cocktails And Coconuts

Departure Jan 15, 2026
Duration 7 days
Starting from
$2,107
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Costa Cruises
Costa Fascinosa

7 days, round-trip Caribbean from Santo Domingo

Departure Jan 12, 2026
Duration 7 days
Starting from
$1,047
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Disney Cruise Line Cruises
Disney Destiny

5 days, round-trip Bahamian Cruise From Fort Lauderdale

Departure Jan 12, 2026
Duration 5 days
Starting from
$3,086
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Celebrity Cruises
Celebrity Ascent

11 days, round-trip Best of Southern Caribbean

Departure Jan 12, 2026
Duration 11 days
Starting from
$7,498
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Marella Cruises
Marella Discovery

7 days, round-trip Caribbean Charms

Departure Jan 13, 2026
Duration 7 days
Starting from
$2,349
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MSC Explora Journeys Cruises
MSC Explora 1

8 days, one-way from Miami to San Juan

Departure Jan 13, 2026
Duration 8 days
Starting from
$4,465
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Norwegian Cruise Line Cruises
Norwegian Pearl

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

Departure Jan 13, 2026
Duration 11 days
Starting from
$1,439
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Viking Cruises
Viking Mars

14 days, round-trip Panama Canal Central America

Departure Jan 13, 2026
Duration 14 days
Starting from
$6,899
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MSC Explora Journeys Cruises
MSC Explora 1

15 days, round-trip An Extended Journey of Fabled Ports, Volcanic Isles and Soft Sands

Departure Jan 13, 2026
Duration 15 days
Starting from
$8,010
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Princess Cruises
Majestic Princess

8 days, round-trip Southern Caribbean with ABC Islands

Departure Jan 17, 2026
Duration 8 days
Starting from
$1,488
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Princess Cruises
Majestic Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 17, 2026
Duration 14 days
Starting from
$3,258
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Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Jan 17, 2026
Duration 7 days
Starting from
$1,440
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Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Jan 17, 2026
Duration 7 days
Starting from
$1,231
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Carnival Cruise Line Cruises
Carnival Miracle

8 days, round-trip Caribbean Panama

Departure Jan 17, 2026
Duration 8 days
Starting from
$1,354
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Azamara Cruises
Azamara Quest

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

Departure Jan 17, 2026
Duration 14 days
Starting from
$4,409
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Disney Cruise Line Cruises
Disney Destiny

5 days, round-trip Western Caribbean Cruise From Fort Lauderdale

Departure Jan 17, 2026
Duration 5 days
Starting from
$3,497
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Silversea Cruises
Silver Ray

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

Departure Jan 16, 2026
Duration 11 days
Starting from
$8,700
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Silversea Cruises
Silver Spirit

10 days, one-way from Fort Lauderdale to Bridgetown

Departure Jan 16, 2026
Duration 10 days
Starting from
$7,000
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Princess Cruises
Caribbean Princess

12 days, round-trip Circle Caribbean

Departure Jan 16, 2026
Duration 12 days
Starting from
$1,488
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Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Miami, Grand Turk back

Departure Jan 16, 2026
Duration 5 days
Starting from
$2,950
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Disney Cruise Line Cruises
Disney Treasure

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

Departure Jan 17, 2026
Duration 7 days
Starting from
$5,124
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Princess Cruises
Enchanted Princess

20 days, round-trip Caribbean Explorer

Departure Jan 16, 2026
Duration 20 days
Starting from
$3,127
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Princess Cruises
Enchanted Princess

10 days, round-trip Southern Caribbean with Martinique

Departure Jan 16, 2026
Duration 10 days
Starting from
$1,759
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Disney Cruise Line Cruises
Disney Wish

3 days, round-trip Bahamian Cruise From Port Canaveral

Departure Jan 16, 2026
Duration 3 days
Starting from
$2,300
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MSC Explora Journeys Cruises
MSC Explora 2

20 days, round-trip An Extended Journey of Island Escapes, Colourful Shores and Tranquil Retreats

Departure Jan 15, 2026
Duration 20 days
Starting from
$10,875
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Lindblad Expeditions Cruises
National Geographic Quest

7 days, round-trip 7 Night The Panama Canal Pearl Islands and Darien Jungle Tropical Wonders and Vibrant Cultures Cruise

Departure Jan 16, 2026
Duration 7 days
Starting from
$7,539
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MSC Explora Journeys Cruises
MSC Explora 2

10 days, round-trip A Journey of Miami Magnetism Lesser Antilles Allure

Departure Jan 15, 2026
Duration 10 days
Starting from
$5,890
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Disney Cruise Line Cruises
Disney Dream

3 days, round-trip Bahamian Cruise From Fort Lauderdale

Departure Jan 16, 2026
Duration 3 days
Starting from
$1,822
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Disney Cruise Line Cruises
Disney Magic

5 days, round-trip Western Caribbean Cruise From Galveston

Departure Jan 16, 2026
Duration 5 days
Starting from
$2,378
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Azamara Cruises
Azamara Quest

22 days, one-way from Bridgetown to Buenos Aires

Departure Jan 17, 2026
Duration 22 days
Starting from
$6,849
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Windstar Cruises
Star Pride

8 days, one-way from Oranjestad Aruba to Panama City

Departure Jan 17, 2026
Duration 8 days
Starting from
$3,099
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Oceania Cruises
Oceania Nautica

10 days, one-way from Miami to Panama City

Departure Jan 17, 2026
Duration 10 days
Starting from
$2,145
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Star Clippers Cruises
Star Flyer

7 days, round-trip Treasure Islands

Departure Jan 17, 2026
Duration 7 days
Starting from
$1,970
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Star Clippers Cruises
Star Clipper

11 days, one-way from Montego Bay to St Johns Antigua

Departure Jan 17, 2026
Duration 11 days
Starting from
$3,090
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Star Clippers Cruises
Royal Clipper

7 days, round-trip Grenadine Islands

Departure Jan 17, 2026
Duration 7 days
Starting from
$2,030
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Oceania Cruises
Oceania Nautica

20 days, round-trip Caribbean Kaleidoscope Miami to Miami

Departure Jan 17, 2026
Duration 20 days
Starting from
$5,799
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Emerald Cruises
Emerald Sakara

7 days, one-way from Bridgetown to Marigot

Departure Jan 17, 2026
Duration 7 days
Starting from
$12,118
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Virgin Voyages Cruises
Valiant Lady

7 days, round-trip St. Kitts, Barbados, Martinique More

Departure Jan 17, 2026
Duration 7 days
Starting from
$1,946
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Emerald Cruises
Emerald Azzurra

6 days, one-way from San Juan to Montserrat Island UK

Departure Jan 17, 2026
Duration 6 days
Starting from
$5,080
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Emerald Cruises
Emerald Azzurra

14 days, round-trip Discover the yachting islands of the Caribbean

Departure Jan 17, 2026
Duration 14 days
Starting from
$9,526
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MSC Cruises
MSC Divina

17 days, round-trip Caribbean Bahamas

Departure Jan 15, 2026
Duration 17 days
Starting from
$1,431
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Oceania Cruises
Oceania Insignia

12 days, one-way from Miami to Bridgetown

Departure Jan 15, 2026
Duration 12 days
Starting from
$2,800
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Oceania Cruises
Oceania Insignia

31 days, one-way from Miami to Bridgetown

Departure Jan 15, 2026
Duration 31 days
Starting from
$8,899
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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.