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
⭐

976

Premium Deals
$1000+
⭐ Premium Deals (89 total)
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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
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
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
Royal Caribbean Cruises
Odyssey Of The Seas

11 days, round-trip Eastern Caribbean Cruise

Departure Nov 5, 2025
Duration 11 days
Starting from
$1,537
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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
Royal Caribbean Cruises
Adventure Of The Seas

10 days, round-trip Southern Caribbean Cruise

Departure Nov 12, 2025
Duration 10 days
Starting from
$1,516
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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 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
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
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 Caribbean
Royal Caribbean Cruises
Symphony Of The Seas

7 days, round-trip Eastern Caribbean Cruise

Departure Nov 23, 2025
Duration 7 days
Starting from
$1,241
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Nov 23, 2025
Duration 7 days
Starting from
$1,864
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⭐ Premium Deals Bahamas
Royal Caribbean Cruises
Odyssey Of The Seas

7 days, round-trip Perfect Day Bahamas Cruise

Departure Nov 23, 2025
Duration 7 days
Starting from
$1,024
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Oasis Of The Seas

6 days, round-trip Western Caribbean Cruise

Departure Nov 23, 2025
Duration 6 days
Starting from
$1,010
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 23, 2025
Duration 7 days
Starting from
$1,499
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Harmony Of The Seas

7 days, round-trip Western Caribbean Cruise

Departure Nov 23, 2025
Duration 7 days
Starting from
$1,336
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Nov 29, 2025
Duration 7 days
Starting from
$1,386
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Oasis Of The Seas

8 days, round-trip Southern Caribbean Perfect Day

Departure Nov 29, 2025
Duration 8 days
Starting from
$1,054
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Vision Of The Seas

12 days, round-trip Southern Caribbean Cruise

Departure Nov 29, 2025
Duration 12 days
Starting from
$1,106
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Nov 30, 2025
Duration 7 days
Starting from
$1,743
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Nov 30, 2025
Duration 7 days
Starting from
$1,201
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Adventure Of The Seas

6 days, round-trip Western Caribbean Cruise

Departure Dec 6, 2025
Duration 6 days
Starting from
$1,077
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Dec 6, 2025
Duration 7 days
Starting from
$1,519
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Allure Of The Seas

8 days, round-trip Eastern Caribbean Perfect Day

Departure Dec 6, 2025
Duration 8 days
Starting from
$1,048
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Dec 7, 2025
Duration 7 days
Starting from
$1,520
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Dec 7, 2025
Duration 7 days
Starting from
$1,621
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Mariner Of The Seas

5 days, round-trip Western Caribbean Cruise

Departure Dec 8, 2025
Duration 5 days
Starting from
$1,122
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

8 days, round-trip Southern Caribbean Cruise

Departure Dec 12, 2025
Duration 8 days
Starting from
$1,325
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Oasis Of The Seas

8 days, round-trip Southern Caribbean Perfect Day

Departure Dec 13, 2025
Duration 8 days
Starting from
$1,022
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Dec 13, 2025
Duration 7 days
Starting from
$1,480
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Dec 14, 2025
Duration 7 days
Starting from
$1,840
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Dec 14, 2025
Duration 7 days
Starting from
$1,865
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Allure Of The Seas

8 days, round-trip Eastern Caribbean Perfect Day

Departure Dec 20, 2025
Duration 8 days
Starting from
$1,542
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Dec 20, 2025
Duration 7 days
Starting from
$1,261
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Icon Of The Seas

7 days, round-trip Eastern Caribbean Perfect Day

Departure Dec 20, 2025
Duration 7 days
Starting from
$1,981
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⭐ Premium Deals Bahamas
Royal Caribbean Cruises
Utopia Of The Seas

3 days, round-trip Bahamas Perfect Day Cruise

Departure Dec 19, 2025
Duration 3 days
Starting from
$1,009
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⭐ Premium Deals Bahamas
Royal Caribbean Cruises
Vision Of The Seas

8 days, round-trip Southeast Coast Bahamas

Departure Dec 19, 2025
Duration 8 days
Starting from
$1,070
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Independence Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Dec 21, 2025
Duration 7 days
Starting from
$1,119
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Harmony Of The Seas

7 days, round-trip Western Caribbean Cruise

Departure Dec 21, 2025
Duration 7 days
Starting from
$1,176
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⭐ Premium Deals Bahamas
Royal Caribbean Cruises
Utopia Of The Seas

4 days, round-trip Bahamas Perfect Day Cruise

Departure Dec 22, 2025
Duration 4 days
Starting from
$1,038
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Mariner Of The Seas

7 days, round-trip Western Caribbean Holiday

Departure Dec 22, 2025
Duration 7 days
Starting from
$1,035
View Deal
⭐ Premium Deals Bahamas
Royal Caribbean Cruises
Odyssey Of The Seas

7 days, round-trip Perfect Day Bahamas Cruise

Departure Dec 21, 2025
Duration 7 days
Starting from
$1,392
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⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Symphony Of The Seas

7 days, round-trip Eastern Caribbean Cruise

Departure Dec 21, 2025
Duration 7 days
Starting from
$1,360
View Deal
⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Serenade Of The Seas

7 days, round-trip Southern Caribbean Cruise

Departure Dec 21, 2025
Duration 7 days
Starting from
$1,508
View Deal
⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Star Of The Seas

7 days, round-trip Western Caribbean Perfect Day

Departure Dec 21, 2025
Duration 7 days
Starting from
$1,964
View Deal
⭐ Premium Deals Caribbean
Royal Caribbean Cruises
Adventure Of The Seas

8 days, round-trip Eastern Caribbean Cruise

Departure Dec 26, 2025
Duration 8 days
Starting from
$1,560
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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.