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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400

Budget Deals
Under $500
💎

703

Mid-Range Deals
$500-$1000
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1,086

Premium Deals
$1000+
⭐ Premium Deals (410 total)
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

8 days, round-trip Brilliant Lady Miami MerMaiden

Departure Oct 17, 2025
Duration 8 days
Starting from
$2,544
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Oct 18, 2025
Duration 7 days
Starting from
$1,431
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

7 days, round-trip Halloween On The High Seas Western Caribbean Cruise From Port Canaveral

Departure Oct 18, 2025
Duration 7 days
Starting from
$4,567
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Oct 18, 2025
Duration 7 days
Starting from
$1,263
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Oasis Of The Seas

8 days, round-trip Southern Caribbean Perfect Day

Departure Oct 18, 2025
Duration 8 days
Starting from
$1,178
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⭐ Premium Deals
Lindblad Expeditions Cruises
National Geographic Quest

7 days, one-way from Panama City to Cartagena Colombia

Departure Oct 19, 2025
Duration 7 days
Starting from
$6,741
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⭐ Premium Deals Caribbean
Margaritaville at Sea Cruises
Margaritaville Islander

7 days, round-trip Jamaica Western Caribbean

Departure Oct 19, 2025
Duration 7 days
Starting from
$1,028
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Oct 19, 2025
Duration 7 days
Starting from
$1,464
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⭐ Premium Deals
Windstar Cruises
Star Pride

7 days, one-way from New York to San Juan

Departure Oct 19, 2025
Duration 7 days
Starting from
$1,999
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Oct 19, 2025
Duration 7 days
Starting from
$1,761
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⭐ Premium Deals
Carnival Cruise Line Cruises
Carnival Pride

7 days, round-trip Bermuda

Departure Oct 19, 2025
Duration 7 days
Starting from
$1,079
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Harmony Of The Seas

7 days, round-trip Western Caribbean Cruise

Departure Oct 19, 2025
Duration 7 days
Starting from
$1,034
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Oct 25, 2025
Duration 7 days
Starting from
$1,163
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Oct 26, 2025
Duration 7 days
Starting from
$1,783
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

7 days, round-trip Halloween On The High Seas Eastern Caribbean Cruise From Port Canaveral

Departure Oct 25, 2025
Duration 7 days
Starting from
$4,929
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Oct 25, 2025
Duration 7 days
Starting from
$1,438
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⭐ Premium Deals Caribbean
Margaritaville at Sea Cruises
Margaritaville Islander

7 days, round-trip Mexico Western Caribbean

Departure Oct 26, 2025
Duration 7 days
Starting from
$1,042
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⭐ Premium Deals
Windstar Cruises
Star Pride

7 days, round-trip San Juan the Virgin Islands

Departure Oct 26, 2025
Duration 7 days
Starting from
$2,159
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Oct 26, 2025
Duration 7 days
Starting from
$1,759
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Magic

7 days, round-trip Halloween On The High Seas Southern Caribbean Cruise From San Juan

Departure Oct 24, 2025
Duration 7 days
Starting from
$2,522
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⭐ Premium Deals Bahamas
Norwegian Cruise Line Cruises
Norwegian Aqua

7 days, round-trip Caribbean Bahamas Dominican Republic

Departure Oct 26, 2025
Duration 7 days
Starting from
$1,049
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Magic

7 days, round-trip Halloween On The High Seas Southern Caribbean Cruise From San Juan

Departure Oct 31, 2025
Duration 7 days
Starting from
$2,864
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⭐ Premium Deals
Azamara Cruises
Azamara Quest

8 days, one-way from Miami to San Juan

Departure Oct 31, 2025
Duration 8 days
Starting from
$2,039
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

7 days, round-trip Scarlets Haunted Halloween Soireacutee

Departure Oct 31, 2025
Duration 7 days
Starting from
$1,666
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Nov 1, 2025
Duration 7 days
Starting from
$1,459
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Prima

7 days, round-trip Caribbean Great Stirrup Cay Cozumel

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,099
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⭐ Premium Deals
Windstar Cruises
Star Pride

7 days, round-trip San Juan the Virgin Islands

Departure Nov 2, 2025
Duration 7 days
Starting from
$2,319
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⭐ Premium Deals
Royal Caribbean Cruises
Brilliance Of The Seas

7 days, one-way from Boston to San Juan

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,198
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

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

Departure Nov 1, 2025
Duration 7 days
Starting from
$4,357
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⭐ Premium Deals
Celebrity Cruises
Celebrity Silhouette

8 days, round-trip Aruba, Curacao Bonaire

Departure Nov 1, 2025
Duration 8 days
Starting from
$1,297
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 1, 2025
Duration 7 days
Starting from
$1,263
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Oasis Of The Seas

8 days, round-trip Southern Caribbean Perfect Day

Departure Nov 1, 2025
Duration 8 days
Starting from
$1,104
View Deal
⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Brilliant Lady

7 days, round-trip Western Caribbean From Miami to Bimini

Departure Nov 1, 2025
Duration 7 days
Starting from
$2,226
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,681
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⭐ Premium Deals
Lindblad Expeditions Cruises
National Geographic Quest

7 days, one-way from Panama City to Cartagena Colombia

Departure Nov 2, 2025
Duration 7 days
Starting from
$6,741
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

6 days, one-way from Miami to San Juan

Departure Nov 2, 2025
Duration 6 days
Starting from
$1,428
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⭐ Premium Deals Caribbean
Margaritaville at Sea Cruises
Margaritaville Islander

7 days, round-trip Mexico Western Caribbean

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,525
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 2, 2025
Duration 7 days
Starting from
$1,461
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 8, 2025
Duration 7 days
Starting from
$1,307
View Deal
⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

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

Departure Nov 8, 2025
Duration 7 days
Starting from
$5,475
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Allure Of The Seas

8 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 8, 2025
Duration 8 days
Starting from
$1,042
View Deal
⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Magic

7 days, round-trip Southern Caribbean Cruise From San Juan

Departure Nov 7, 2025
Duration 7 days
Starting from
$2,676
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⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Resilient Lady

6 days, round-trip Western Caribbean Charm

Departure Nov 9, 2025
Duration 6 days
Starting from
$1,298
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⭐ Premium Deals
Celebrity Cruises
Celebrity Beyond

7 days, round-trip St. Thomas Puerto Plata

Departure Nov 9, 2025
Duration 7 days
Starting from
$1,026
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 9, 2025
Duration 7 days
Starting from
$1,468
View Deal
⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Nov 9, 2025
Duration 7 days
Starting from
$1,528
View Deal
⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Saint Isles Seas of the Caribbean

Departure Nov 8, 2025
Duration 7 days
Starting from
$2,926
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⭐ Premium Deals
Azamara Cruises
Azamara Quest

7 days, one-way from San Juan to Bridgetown

Departure Nov 8, 2025
Duration 7 days
Starting from
$2,209
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⭐ Premium Deals Caribbean
Princess Cruises
Majestic Princess

8 days, round-trip Southern Caribbean with ABC Islands

Departure Nov 8, 2025
Duration 8 days
Starting from
$1,128
View Deal
⭐ Premium Deals
Windstar Cruises
Star Pride

7 days, round-trip San Juan the Virgin Islands

Departure Nov 9, 2025
Duration 7 days
Starting from
$2,318
View Deal
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.