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
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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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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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
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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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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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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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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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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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
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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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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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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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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Marella Cruises
Marella Discovery

7 days, round-trip Tropical Isles

Departure Jan 20, 2026
Duration 7 days
Starting from
$2,054
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Seabourn Cruises
Seabourn Ovation

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

Departure Jan 24, 2026
Duration 7 days
Starting from
$4,079
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Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cayman Coves Jamaican Waterfalls

Departure Jan 24, 2026
Duration 7 days
Starting from
$2,366
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Star Clippers Cruises
Star Flyer

7 days, round-trip Leeward Islands

Departure Jan 24, 2026
Duration 7 days
Starting from
$1,970
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Star Clippers Cruises
Royal Clipper

7 days, round-trip Windward Islands

Departure Jan 24, 2026
Duration 7 days
Starting from
$2,030
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Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Barbados, Antigua, BVI More

Departure Jan 24, 2026
Duration 7 days
Starting from
$2,786
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Emerald Cruises
Emerald Azzurra

6 days, one-way from Barbuda Island to San Juan

Departure Jan 24, 2026
Duration 6 days
Starting from
$4,829
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Jan 25, 2026
Duration 7 days
Starting from
$1,558
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Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Jan 25, 2026
Duration 7 days
Starting from
$1,228
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Marella Cruises
Marella Explorer

7 days, round-trip A Taste Of The Tropics

Departure Jan 25, 2026
Duration 7 days
Starting from
$2,280
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Windstar Cruises
Wind Surf

7 days, one-way from Bridgetown to Oranjestad Aruba

Departure Jan 25, 2026
Duration 7 days
Starting from
$3,299
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Celebrity Cruises
Celebrity Xcel

7 days, round-trip Puerto Plata, St. Thomas St. Maarten

Departure Jan 25, 2026
Duration 7 days
Starting from
$1,143
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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.