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 (54 total)
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

15 days, one-way from Barcelona to Miami

Departure Oct 16, 2025
Duration 15 days
Starting from
$3,900
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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
Virgin Voyages Cruises
Valiant Lady

5 days, round-trip Riviera Maya Halloween Edition

Departure Oct 19, 2025
Duration 5 days
Starting from
$1,690
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

5 days, round-trip Dominican Daze Halloween Edition

Departure Oct 24, 2025
Duration 5 days
Starting from
$1,792
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

14 days, one-way from Barcelona to Miami

Departure Oct 26, 2025
Duration 14 days
Starting from
$3,080
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

4 days, round-trip Valiants Haunted Halloween Soireacutee

Departure Oct 29, 2025
Duration 4 days
Starting from
$1,834
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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
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
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
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Dominican Daze

Departure Nov 7, 2025
Duration 5 days
Starting from
$1,792
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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
Virgin Voyages Cruises
Brilliant Lady

12 days, round-trip Colorful Curaccedilao to the Charming Caymans

Departure Nov 8, 2025
Duration 12 days
Starting from
$3,576
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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
Virgin Voyages Cruises
Scarlet Lady

4 days, round-trip Fire Sunset Soireacutees

Departure Nov 12, 2025
Duration 4 days
Starting from
$1,602
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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
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Riviera Maya

Departure Nov 16, 2025
Duration 5 days
Starting from
$1,090
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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
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
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
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Miami, Grand Turk back

Departure Nov 21, 2025
Duration 5 days
Starting from
$2,190
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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
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

9 days, round-trip Antigua Waves Grand Turk Caves

Departure Nov 28, 2025
Duration 9 days
Starting from
$2,322
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

4 days, round-trip Fire Sunset Soireacutees

Departure Nov 26, 2025
Duration 4 days
Starting from
$1,802
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

6 days, round-trip San Juan to Barbados the St. Isles

Departure Nov 29, 2025
Duration 6 days
Starting from
$1,550
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip San Juan, Samanaacute Bimini

Departure Nov 29, 2025
Duration 7 days
Starting from
$1,522
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Miami, Grand Turk back

Departure Nov 30, 2025
Duration 5 days
Starting from
$2,200
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

8 days, round-trip Nicky Jam x Virgin Voyages

Departure Dec 5, 2025
Duration 8 days
Starting from
$2,066
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cayman Coves Jamaican Waterfalls

Departure Dec 6, 2025
Duration 7 days
Starting from
$1,806
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Dominican Daze

Departure Dec 5, 2025
Duration 5 days
Starting from
$1,792
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

11 days, round-trip Aruban Sunsets Calm Cayman Days

Departure Dec 7, 2025
Duration 11 days
Starting from
$2,840
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

4 days, round-trip Fire Sunset Soireacutees

Departure Dec 10, 2025
Duration 4 days
Starting from
$1,522
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cayman Coves Jamaican Waterfalls

Departure Dec 13, 2025
Duration 7 days
Starting from
$1,668
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Riviera Maya

Departure Dec 14, 2025
Duration 5 days
Starting from
$1,090
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip St. Lucia, St. Maarten, Barbados More

Departure Dec 13, 2025
Duration 7 days
Starting from
$1,806
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⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Brilliant Lady

8 days, round-trip Brilliant Caribbean Holidays

Departure Dec 18, 2025
Duration 8 days
Starting from
$2,384
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Miami, Grand Turk back

Departure Dec 19, 2025
Duration 5 days
Starting from
$1,800
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⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Valiant Caribbean Holidays

Departure Dec 20, 2025
Duration 7 days
Starting from
$2,590
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⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Resilient Caribbean Holidays

Departure Dec 20, 2025
Duration 7 days
Starting from
$2,926
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⭐ Premium Deals Caribbean
Virgin Voyages Cruises
Scarlet Lady

4 days, round-trip Scarlet Caribbean Holidays

Departure Dec 24, 2025
Duration 4 days
Starting from
$1,514
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Dominican Daze

Departure Jan 2, 2026
Duration 5 days
Starting from
$1,792
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cozumel, Grand Cayman Bimini

Departure Jan 3, 2026
Duration 7 days
Starting from
$1,662
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Aruban Sights Antiguan

Departure Jan 3, 2026
Duration 7 days
Starting from
$2,508
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⭐ Premium Deals
Virgin Voyages Cruises
Brilliant Lady

11 days, round-trip Aruba, Bonaire, Colombia, Jamaica More

Departure Jan 4, 2026
Duration 11 days
Starting from
$3,632
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

4 days, round-trip Fire Sunset Soireacutees

Departure Jan 7, 2026
Duration 4 days
Starting from
$1,352
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip Virgin Island Views Saint Isle Blues

Departure Jan 10, 2026
Duration 7 days
Starting from
$1,948
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⭐ Premium Deals
Virgin Voyages Cruises
Resilient Lady

7 days, round-trip Cayman Isles Jamaican Miles

Departure Jan 10, 2026
Duration 7 days
Starting from
$2,226
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Riviera Maya

Departure Jan 11, 2026
Duration 5 days
Starting from
$1,490
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⭐ Premium Deals
Virgin Voyages Cruises
Scarlet Lady

5 days, round-trip Miami, Grand Turk back

Departure Jan 16, 2026
Duration 5 days
Starting from
$2,950
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⭐ Premium Deals
Virgin Voyages Cruises
Valiant Lady

7 days, round-trip St. Kitts, Barbados, Martinique More

Departure Jan 17, 2026
Duration 7 days
Starting from
$1,946
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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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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.