$203 Find Cheap Flights from Key West to Caribbean - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Key West to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Nassau
Nassau1 stop$472
Kingston
Kingston2 stops$1,389
Nassau
Nassau1 stop$472
Kingston
Kingston2 stops$1,389

KAYAK's insights & trends for Key West to Caribbean flights

Get data-powered insights and trends into flights from Key West to Caribbean to help you find the cheapest flights, the best time to fly and much more.

Which airlines provide the cheapest flights from Key West to Caribbean?

In the past 5 days, the cheapest round-trip tickets from Key West to Caribbean were found on American Airlines ($602) and WestJet ($2,629).

Good to know

Cheapest flight

$203
Flight from Key West to Nassau

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Key West to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Key West to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Key West to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Key West to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Key West to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Key West to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Key West to Caribbean

 
Need help choosing which airline to fly with from Key West to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.0
American AirlinesOverall score based on 12181 reviews
6.8Entertainment
7.4Boarding
7.1Comfort
7.9Crew
6.4Food
Airline reviews

This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.

2.0 MediocreSean, Oct 2026
Read more American Airlines reviews

This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.

Cabin was bone dry, no humidity whatsoever, and pretty warm; and beverage service didn't start for at least an hour. I had to go to the back for water and the FAs tried telling me it was always this way for all Miami flights, which is complete nonsense. Avoid the MAX8 like the plague.

Im sitting here waiting over an hour for my golf clubs

Flight was 2+ hours delayed and they “misplaced” all 3 of our checked-in bags.

Overall, really good experience, on time and the comfort was there. Wi-Fi was easy to connect

Flight was delayed 5 hours only to be cancelled at 1:30am. I did not get on the rescheduled flight because of worry it would be delayed (which it was). I needed to drive home. Horrible.

When there are many passengers who are going to miss a connecting flight, they always say please let them off first. But the flight attendant never manages that part of the process. It would be helpful if they would repeat that and stress that to the other passengers.

Flight was delayed due to maintenance issue. Missed my connecting flight. Got rebooked in a middle seat when I had a first class ticket.

My boarding pass said gate E5. I arrived at gate E5 by 12:45pm. At 2:10pm, I received a phone call stating I was supposed to be at gate D37. They would not wait for me to get there (by the way, the plane was still there when I got to gate D37, but everything was closed and no one was at the door). The next flight at 7:40pm was sold out; was told I'd be put on the 9:47pm flight. I was so stressed, I became chokey (apparently I have mild asthma). By the grace of God, a lot of begging, and the customer service rep taking pity on me, I was able to get on a 4:50pm flight to Philadelphia.

I have never been assaulted they way I was today in Charlotte - shame on American

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental