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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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Holland America, Nieuw Amsterdam
Discount
Nieuw Amsterdam12 Nights Eastern Caribbean Cruise from $1204 pp
12 Night - Eastern Caribbean : Barbados, St. Lucia & St. Kitts - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, Fort-De-France, Martinique, Bridgetown, Barbados, Scarborough, Trinidad and Tobago, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, Key West, Florida, Fort Lauderdale, Florida
2026 Sails: Nov 29 Get a Quote
Holland America, Nieuw Amsterdam
Discount
Nieuw Amsterdam12 Night Eastern Caribbean Cruise: Barbados, St. Lucia & & Bahamas $952 pp
12 Night - Eastern Caribbean : Barbados, St. Lucia & St. Kitts - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, Fort-De-France, Martinique, Bridgetown, Barbados, Scarborough, Trinidad and Tobago, Castries, Saint Lucia, Basseterre, St Kitts and Nevis, Key West, Florida, Fort Lauderdale, Florida
2026 Sails: Nov 29 Get a Quote
Holland America, Nieuw Amsterdam
Discount
Nieuw Amsterdam16 Nights Eastern Caribbean Holiday Cruise Amber Cove & Bahamas $1241 pp
16 Night - Eastern Caribbean Holiday : Amber Cove & Bahamas - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Road Town (Tortola), British Virgin Islands, San Juan, Puerto Rico, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Key West, Florida, Fort Lauderdale, Florida
2026 Sails: Dec 11 Get a Quote
Holland America, Nieuw Amsterdam
Discount
Nieuw Amsterdam16 Nights Eastern Caribbean Holiday Cruise Amber Cove & Bahamas $1241pp
16 Night - Eastern Caribbean Holiday : Amber Cove & Bahamas - Starting in Fort Lauderdale, Florida, Philipsburg, Sint Maarten, St Johns AG, Antigua, Road Town (Tortola), British Virgin Islands, San Juan, Puerto Rico, RelaxAway, Half Moon Cay, Bahamas, Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Key West, Florida, Fort Lauderdale, Florida
2026 Sails: Dec 11 Get a Quote
Holland America, Zuiderdam
Discount
Zuiderdam14 Nights Eastern & Western Caribbean Cruise from $953 pp
14 Night - Western & Eastern Caribbean : Mexico & Bahamas Holiday - Starting in Miami, Florida, RelaxAway, Half Moon Cay, Bahamas, Ocho Rios, Jamaica, Georgetown, Cayman Islands, Cozumel, Mexico, Miami, Florida, Amber Cove, Dominican Republic, Grand Turk, Turks and Caicos, RelaxAway, Half Moon Cay, Bahamas, Key West, Florida, Miami, Florida
2026 Sails: Dec 12 Get a Quote
Holland America, Zuiderdam
Discount
Zuiderdam14 Nights Eastern Caribbean Cruise from $1231 pp plus OBC
14 Night - Eastern Caribbean : Bahamas & San Juan Holiday - Starting in Miami, Florida, Amber Cove, Dominican Republic, Grand Turk, Turks and Caicos, RelaxAway, Half Moon Cay, Bahamas, Key West, Florida, Miami, Florida, Grand Turk, Turks and Caicos, San Juan, Puerto Rico, St Thomas, US Virgin Islands, RelaxAway, Half Moon Cay, Bahamas, Miami, Florida
2026 Sails: Dec 19 Get a Quote
Oceania Cruises, Oceania Insignia
Discount
Oceania Insignia15 Nights Antilles To Andes Voyage from $4399 pp
15 Night - Antilles to Andes - Starting in Miami, Key West, Willemstad AN, Oranjestad, Santa Marta, Cartagena CO, Panama Canal Daylight Transit, Manta, Guayaquil, Lima / Machu Picchu (Callao)
2026 Sails: Dec 19 Get a Quote
Holland America, Nieuw Amsterdam
Discount
Nieuw Amsterdam19 Nights Panama Canal Holiday Cruise Amber Cove & Costa Rica $1836pp plus
19 Night - Panama Canal Holiday : Amber Cove & Costa Rica - Starting in Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Key West, Florida, Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Oranjestad, Aruba, Cartagena CO, Enter Panama Canal Cristobal, Cruising Panama Canal and Gatun Lake, Gatun Lake, Panama, Cruising Gatun Lake and Panama Canal, Exit Panama Canal Cristobal, Colon, Panama, Puerto Limon (San Jose), Costa Rica, Georgetown, Cayman Islands, Fort Lauderdale, Florida
2026 Sails: Dec 20 Get a Quote
Holland America, Nieuw Amsterdam
Discount
Nieuw Amsterdam7 Nights Eastern Caribbean Holiday Cruise: Amber Cove & Bahamas $608 pp
7 Night - Eastern Caribbean Holiday : Amber Cove & Bahamas - Starting in Fort Lauderdale, Florida, RelaxAway, Half Moon Cay, Bahamas, Grand Turk, Turks and Caicos, Amber Cove, Dominican Republic, Key West, Florida, Fort Lauderdale, Florida
2026 Sails: Dec 20 Get a Quote
Holland America, Volendam
Family
Volendam14 Nights Southern Caribbean Cruise from $1467 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

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Key West Cruise Specials