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
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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⭐ Premium Deals
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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⭐ Premium Deals
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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⭐ Premium Deals
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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⭐ Premium Deals
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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⭐ Premium Deals Caribbean
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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⭐ Premium Deals
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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⭐ Premium Deals
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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⭐ Premium Deals
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.