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 Seeker

8 days, one-way from Miami to San Juan

Departure Jan 15, 2026
Duration 8 days
Starting from
$7,949
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Jan 18, 2026
Duration 7 days
Starting from
$1,681
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Jan 18, 2026
Duration 7 days
Starting from
$1,378
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Disney Cruise Line Cruises
Disney Fantasy

5 days, round-trip Bahamian Cruise From Port Canaveral With Pixar Day At Sea

Departure Jan 18, 2026
Duration 5 days
Starting from
$2,887
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⭐ Premium Deals Caribbean
Princess Cruises
Grand Princess

14 days, round-trip Southern Caribbean Adventurer

Departure Jan 18, 2026
Duration 14 days
Starting from
$1,159
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⭐ Premium Deals
Marella Cruises
Marella Explorer

7 days, round-trip Paradise Islands

Departure Jan 18, 2026
Duration 7 days
Starting from
$2,038
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Dream

4 days, round-trip Bahamian Cruise From Fort Lauderdale

Departure Jan 19, 2026
Duration 4 days
Starting from
$2,203
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Wish

4 days, round-trip Bahamian Cruise From Port Canaveral

Departure Jan 19, 2026
Duration 4 days
Starting from
$3,216
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⭐ Premium Deals
Cunard Cruises
Queen Mary 2

15 days, one-way from New York to Los Angeles

Departure Jan 19, 2026
Duration 15 days
Starting from
$2,389
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⭐ Premium Deals
Seabourn Cruises
Seabourn Ovation

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

Departure Jan 17, 2026
Duration 7 days
Starting from
$4,249
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Spirit

14 days, round-trip Southern Caribbean

Departure Jan 17, 2026
Duration 14 days
Starting from
$1,694
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⭐ Premium Deals Caribbean
Seabourn Cruises
Seabourn Ovation

14 days, round-trip Gems Of The Caribbean

Departure Jan 17, 2026
Duration 14 days
Starting from
$7,564
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⭐ Premium Deals
Celebrity Cruises
Celebrity Eclipse

8 days, round-trip Antigua, St. Maarten, San Juan Puerto Plata

Departure Jan 17, 2026
Duration 8 days
Starting from
$1,022
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip San Juan, Samanaacute Bimini

Departure Jan 17, 2026
Duration 7 days
Starting from
$2,226
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⭐ Premium Deals Caribbean
MSC Cruises
MSC World America

14 days, round-trip Eastern Western Caribbean

Departure Jan 17, 2026
Duration 14 days
Starting from
$2,286
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⭐ Premium Deals Caribbean
Princess Cruises
Star Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 17, 2026
Duration 14 days
Starting from
$1,518
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from La Romana

Departure Jan 18, 2026
Duration 14 days
Starting from
$1,708
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

7 days, round-trip Caribbean from La Romana

Departure Jan 18, 2026
Duration 7 days
Starting from
$1,009
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Dream

14 days, round-trip Eastern Caribbean

Departure Jan 18, 2026
Duration 14 days
Starting from
$1,709
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⭐ Premium Deals
Silversea Cruises
Silver Shadow

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

Departure Jan 18, 2026
Duration 7 days
Starting from
$5,500
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⭐ Premium Deals
Windstar Cruises
Wind Surf

14 days, one-way from Bridgetown to Oranjestad Aruba

Departure Jan 18, 2026
Duration 14 days
Starting from
$6,099
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⭐ Premium Deals
Windstar Cruises
Wind Surf

7 days, round-trip Jewels of the Windward Islands

Departure Jan 18, 2026
Duration 7 days
Starting from
$3,099
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⭐ Premium Deals
Holland America Cruises
ms Rotterdam

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

Departure Jan 18, 2026
Duration 12 days
Starting from
$1,399
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⭐ Premium Deals Caribbean
Princess Cruises
Sun Princess

14 days, round-trip EasternWestern Caribbean Adventurer

Departure Jan 18, 2026
Duration 14 days
Starting from
$1,478
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⭐ Premium Deals Bahamas
Norwegian Cruise Line Cruises
Norwegian Aqua

7 days, round-trip Caribbean Bahamas Dominican Republic

Departure Jan 18, 2026
Duration 7 days
Starting from
$1,019
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⭐ Premium Deals Caribbean
Holland America Cruises
ms Rotterdam

21 days, round-trip Panama Canal Southern Caribbean Abc Islands

Departure Jan 18, 2026
Duration 21 days
Starting from
$2,384
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Jan 24, 2026
Duration 7 days
Starting from
$1,141
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Vision Of The Seas

12 days, round-trip Southern Caribbean Cruise

Departure Jan 24, 2026
Duration 12 days
Starting from
$1,189
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⭐ Premium Deals Caribbean
Windstar Cruises
Wind Spirit

7 days, round-trip Beach Fun Sun A Remote Caribbean Getaway

Departure Jan 24, 2026
Duration 7 days
Starting from
$3,299
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⭐ Premium Deals Caribbean
Margaritaville at Sea Cruises
Margaritaville Islander

7 days, round-trip Jamaica Western Caribbean

Departure Jan 23, 2026
Duration 7 days
Starting from
$1,335
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⭐ Premium Deals
Windstar Cruises
Star Seeker

7 days, round-trip San Juan the Virgin Islands

Departure Jan 23, 2026
Duration 7 days
Starting from
$5,599
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⭐ Premium Deals Caribbean
Celebrity Cruises
Celebrity Ascent

10 days, round-trip Ultimate Southern Caribbean

Departure Jan 23, 2026
Duration 10 days
Starting from
$1,788
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⭐ Premium Deals
Windstar Cruises
Star Seeker

14 days, round-trip Star Collector Lovely Leewards

Departure Jan 23, 2026
Duration 14 days
Starting from
$17,199
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

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

Departure Jan 24, 2026
Duration 7 days
Starting from
$4,474
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Jan 24, 2026
Duration 7 days
Starting from
$1,420
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⭐ Premium Deals Caribbean
Cunard Cruises
Queen Elizabeth

21 days, round-trip Caribbean

Departure Jan 20, 2026
Duration 21 days
Starting from
$2,514
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⭐ Premium Deals Caribbean
MSC Explora Journeys Cruises
MSC Explora 1

15 days, round-trip An Extended Journey of Caribbean Inspiration and Island Beauty

Departure Jan 21, 2026
Duration 15 days
Starting from
$8,460
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

4 days, round-trip Fire Sunset Soireacutees

Departure Jan 21, 2026
Duration 4 days
Starting from
$1,920
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

7 days, one-way from San Juan to Miami

Departure Jan 21, 2026
Duration 7 days
Starting from
$4,700
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Magic

4 days, round-trip Western Caribbean Cruise From Galveston With Marvel Day At Sea

Departure Jan 21, 2026
Duration 4 days
Starting from
$1,816
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Destiny

4 days, round-trip Bahamian Cruise From Fort Lauderdale

Departure Jan 22, 2026
Duration 4 days
Starting from
$3,410
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⭐ Premium Deals Caribbean
Costa Cruises
Costa Pacifica

14 days, round-trip Caribbean from Guadeloupe

Departure Jan 22, 2026
Duration 14 days
Starting from
$1,752
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⭐ Premium Deals
Marella Cruises
Marella Discovery 2

7 days, round-trip Exotic Islands

Departure Jan 22, 2026
Duration 7 days
Starting from
$2,106
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Dream

3 days, round-trip Bahamian Cruise From Fort Lauderdale

Departure Jan 23, 2026
Duration 3 days
Starting from
$1,684
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Wish

3 days, round-trip Bahamian Cruise From Port Canaveral

Departure Jan 23, 2026
Duration 3 days
Starting from
$2,096
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Fantasy

5 days, round-trip Bahamian Cruise From Port Canaveral With Pixar Day At Sea

Departure Jan 23, 2026
Duration 5 days
Starting from
$3,206
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⭐ Premium Deals
Cunard Cruises
Queen Mary 2

18 days, one-way from New York to San Francisco

Departure Jan 19, 2026
Duration 18 days
Starting from
$1,999
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⭐ Premium Deals
Cunard Cruises
Queen Mary 2

44 days, one-way from New York to Sydney

Departure Jan 19, 2026
Duration 44 days
Starting from
$5,519
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⭐ Premium Deals
Cunard Cruises
Queen Mary 2

109 days, round-trip Full World Voyage

Departure Jan 19, 2026
Duration 109 days
Starting from
$14,829
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⭐ Premium Deals Mexico
Norwegian Cruise Line Cruises
Norwegian Jewel

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

Departure Jan 19, 2026
Duration 11 days
Starting from
$1,259
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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.