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Key West Cruise Specials

We've gathered all of the Key West cruise specials ordered by sail date. Click on a special and select a sail date to get a single cruise quote from the cruise agency that posted that particular special. To search through all cruise itineraries (not just Key West cruises) to receive multiple custom cruise options to compare, please visit our Cruise Search page.

All Cruise Specials


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Oceania Cruises, Oceania Insignia
Discount
Oceania Insignia Cruise Ship36NT Caribbean To Cape Horn From $9,999pp $11499
36 Night - Caribbean to Cape Horn - Starting in Miami, Key West, Willemstad AN, Oranjestad, Santa Marta, Cartagena CO, Panama Canal Daylight Transit, Manta, Salaverry, Lima / Machu Picchu (Callao), Pisco / Nazca Lines, Coquimbo, Santiago De Chile (San Antonio CL), Puerto Montt, Puerto Chacabuco, Laguna San Raphael, Cruising the Chilean Fjords, Punta Arenas, Cruising Around Cape Horn, Ushuaia, Port Stanley, Falkland Islands, Puerto Madryn, Punta Del Este, Buenos Aires
2026 Sails: Dec 19 Get a Quote
Oceania Cruises, Oceania Insignia
Luxury and Exotic
Oceania Insignia Cruise Ship15NT Antilles To Andes From $4,099pp $5499
15 Night - Antilles to Andes - Starting in Miami, Key West, Willemstad AN, Oranjestad, Santa Marta, Cartagena CO, Panama Canal Daylight Transit, Manta, Salaverry, Lima / Machu Picchu (Callao)
2026 Sails: Dec 19 Get a Quote
Oceania Cruises, Oceania Insignia
Luxury and Exotic
Oceania Insignia Cruise Ship36NT Caribbean To Cape Horn From $9,999pp $11499
36 Night - Caribbean to Cape Horn - Starting in Miami, Key West, Willemstad AN, Oranjestad, Santa Marta, Cartagena CO, Panama Canal Daylight Transit, Manta, Salaverry, Lima / Machu Picchu (Callao), Pisco / Nazca Lines, Coquimbo, Santiago De Chile (San Antonio CL), Puerto Montt, Puerto Chacabuco, Laguna San Raphael, Cruising the Chilean Fjords, Punta Arenas, Cruising Around Cape Horn, Ushuaia, Port Stanley, Falkland Islands, Puerto Madryn, Punta Del Este, Buenos Aires
2026 Sails: Dec 19 Get a Quote
Holland America Line, Volendam
Family
HAL Volendam Cruise Ship14 Nights Southern Caribbean Cruise: Abc & Windward Islands from $2026 pp
14 Night - Southern Caribbean : Abc & Windward Islands Holiday - Starting in Fort Lauderdale, Florida, Key West, Florida, Oranjestad, Aruba, Charlotteville, Trinidad and Tobago, Saint Georges, Grenada, Bridgetown, Barbados, Castries, Saint Lucia, San Juan, Puerto Rico, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida
2026 Sails: Dec 22 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I Cruises18 Nights A Journey of Coastal Marvels & Caribbean Dreams from $8460 pp
18 Night - An Extended Journey of Coastal Marvels & Caribbean Dreams - Starting in Miami, Puerto Plata, Dominican Republic, Cayo Levantado, Dominican Republic, San Juan, Charlotte Amalie (Saint Thomas), Spanish Town (Virgin Gorda), Miami, Ocho Rios, Jamaica, Santo Tomas, Roatan Island, Belize City, Key West, Miami
2027 Sails: Jan 11 Get a Quote
Explora Journeys, EXPLORA I
Family
EXPLORA I Cruises9 NT A Journey OfEnchanting Ancient History&Coastal Splendourfrom $4935pp
9 Night - A Journey of Enchanting Ancient History & Coastal Splendour - Starting in Miami, Ocho Rios, Jamaica, Santo Tomas, Roatan Island, Belize City, Key West, Miami
2027 Sails: Jan 20 Get a Quote
Holland America Line, Rotterdam
Family
HAL Rotterdam Cruise Ship10 Nights Western Caribbean Cruise from $1360 pp
10 Night - Western Caribbean : Greater Antilles, Belize & Mexico - Starting in Fort Lauderdale, Florida, Key West, Florida, Georgetown, Cayman Islands, Ocho Rios, Jamaica, Mahogany Bay, Roatan, Honduras, Belize City, Belize, Cozumel, Mexico, Fort Lauderdale, Florida
2027 Sails: Feb 13 Get a Quote
Explora Journeys, EXPLORA III
Family
EXPLORA III Cruises14 NT A Journey from Vibrant Shores to Spectacular Scenery from $7080 pp
14 Night - An Extended Journey from Vibrant Shores to Spectacular Scenery - Starting in Miami, St John VI (Cruz Bay), US Virgin Islands, St Johns AG, Antigua, Terre-De-Haut, Tortola / Road Town, San Juan, Gustavia, Little Bay, Basseterre, Key West, Miami
2027 Sails: Mar 29 Get a Quote
Explora Journeys, EXPLORA III
Discount
EXPLORA III Cruises7 Night A Journey Through Balmy Shores & Stirring Scenery from $4200 pp
7 Night - A Journey Through Balmy Shores & Stirring Scenery - Starting in San Juan, Gustavia, Little Bay, Basseterre, Key West, Miami
2027 Sails: Apr 5 Get a Quote
Explora Journeys, EXPLORA IV
Discount
EXPLORA IV Cruises7 Night A Journey Across the Caribbean's Colourful Heart from $4180 pp
7 Night - A Journey Across the Caribbean's Colourful Heart - Starting in San Juan, Charlotte Amalie (Saint Thomas), Isla Catalina, Puerto Plata, Dominican Republic, Key West, Ocean Cay, Miami
2027 Sails: Nov 13 Get a Quote

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Key West Cruise Specials