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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317

Budget Deals
Under $500
💎

621

Mid-Range Deals
$500-$1000
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976

Premium Deals
$1000+
⭐ Premium Deals (377 total)
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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
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
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 8, 2025
Duration 7 days
Starting from
$1,307
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⭐ 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
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⭐ 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
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⭐ 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
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⭐ 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
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⭐ 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
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⭐ Premium Deals
Celebrity Cruises
Celebrity Ascent

8 days, round-trip Aruba, Curacao Cayman

Departure Nov 13, 2025
Duration 8 days
Starting from
$1,548
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⭐ Premium Deals
Disney Cruise Line Cruises
Disney Magic

6 days, one-way from San Juan to Galveston

Departure Nov 14, 2025
Duration 6 days
Starting from
$2,460
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

8 days, one-way from Miami to San Juan

Departure Nov 12, 2025
Duration 8 days
Starting from
$4,465
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

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

Departure Nov 15, 2025
Duration 7 days
Starting from
$5,057
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,553
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,113
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Oasis Of The Seas

8 days, round-trip Southern Caribbean Perfect Day

Departure Nov 15, 2025
Duration 8 days
Starting from
$1,124
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⭐ Premium Deals
Azamara Cruises
Azamara Quest

7 days, one-way from Bridgetown to San Juan

Departure Nov 15, 2025
Duration 7 days
Starting from
$2,089
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Sunny Miles of Tropical Isles

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,948
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⭐ Premium Deals
Celebrity Cruises
Celebrity Silhouette

8 days, round-trip Aruba, Curacao Bonaire

Departure Nov 15, 2025
Duration 8 days
Starting from
$1,204
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⭐ Premium Deals
Windstar Cruises
Star Pride

7 days, round-trip San Juan the Virgin Islands

Departure Nov 16, 2025
Duration 7 days
Starting from
$2,699
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip San Juan Sunrises Dominican Dreams

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,890
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 16, 2025
Duration 7 days
Starting from
$1,451
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 16, 2025
Duration 7 days
Starting from
$1,754
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⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Joy

7 days, round-trip Caribbean Great Stirrup Cay Dominican Republic

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,449
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⭐ Premium Deals Bahamas
Celebrity Cruises
Celebrity Apex

7 days, round-trip Key West, Bahamas Grand Turk

Departure Nov 15, 2025
Duration 7 days
Starting from
$1,095
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 1

7 days, one-way from San Juan to Miami

Departure Nov 20, 2025
Duration 7 days
Starting from
$3,690
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

8 days, round-trip Sunny San Juan Isles of Beach Miles

Departure Nov 20, 2025
Duration 8 days
Starting from
$2,064
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⭐ Premium Deals
Seabourn Cruises
Seabourn Sojourn

7 days, round-trip Dominican Republic Delights

Departure Nov 18, 2025
Duration 7 days
Starting from
$3,513
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⭐ Premium Deals
Crystal Cruises
Crystal Serenity

8 days, one-way from Bridgetown to Fort Lauderdale

Departure Nov 20, 2025
Duration 8 days
Starting from
$4,200
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Thanksgiving in the Lesser Antilles

Departure Nov 22, 2025
Duration 7 days
Starting from
$1,806
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⭐ Premium Deals
Azamara Cruises
Azamara Quest

7 days, one-way from San Juan to Bridgetown

Departure Nov 22, 2025
Duration 7 days
Starting from
$2,089
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⭐ Premium Deals
Celebrity Cruises
Celebrity Eclipse

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

Departure Nov 22, 2025
Duration 8 days
Starting from
$1,291
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 22, 2025
Duration 7 days
Starting from
$1,587
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⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Jubilee

7 days, round-trip Western Caribbean

Departure Nov 22, 2025
Duration 7 days
Starting from
$1,154
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⭐ Premium Deals Caribbean
Disney Cruise Line Cruises
Disney Treasure

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

Departure Nov 22, 2025
Duration 7 days
Starting from
$7,029
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Allure Of The Seas

8 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 22, 2025
Duration 8 days
Starting from
$1,521
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⭐ Premium Deals
Star Clippers Cruises
Star Flyer

7 days, round-trip Treasure Islands

Departure Nov 22, 2025
Duration 7 days
Starting from
$1,970
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cayman Coves Jamaican Waterfalls

Departure Nov 22, 2025
Duration 7 days
Starting from
$2,086
View Deal
⭐ Premium Deals Caribbean
Norwegian Cruise Line Cruises
Norwegian Joy

7 days, round-trip Caribbean Great Stirrup Cay Dominican Republic

Departure Nov 22, 2025
Duration 7 days
Starting from
$1,399
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⭐ Premium Deals
Celebrity Cruises
Celebrity Apex

7 days, round-trip St. Kitts, San Juan Puerto Plata

Departure Nov 22, 2025
Duration 7 days
Starting from
$1,357
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⭐ Premium Deals
MSC Explora Journeys Cruises
MSC Explora 2

6 days, one-way from Bridgetown to Miami

Departure Nov 22, 2025
Duration 6 days
Starting from
$3,465
View Deal
⭐ Premium Deals Caribbean
Carnival Cruise Line Cruises
Carnival Mardi Gras

7 days, round-trip Eastern Caribbean

Departure Nov 22, 2025
Duration 7 days
Starting from
$1,268
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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.