$195 Find Cheap Flights from Key West to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Key West to Caribbean departing on 7/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
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 72 hours
Nassau
Nassau1 stop$576
Kingston
Kingston2 stops$1,888
Nassau
Nassau1 stop$576
Kingston
Kingston2 stops$1,888

Book Cheap Key West to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Key West to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Caribbean

Wed, Sep 30 - Fri, Oct 2
Multiple Airlines Logo
10:04 am - 11:57 pm
EYW
-
SJU
13h 53m
1 stop
Multiple Airlines Logo
4:39 pm - 9:24 am
SJU
-
EYW
16h 45m
1 stop
$260Multiple Airlines
Wed, Aug 19 - Sun, Aug 23
Multiple Airlines Logo
11:46 am - 12:56 am
EYW
-
SJU
13h 10m
1 stop
Multiple Airlines Logo
5:15 pm - 12:31 pm
SJU
-
EYW
19h 16m
1 stop
$264Multiple Airlines
Fri, Oct 2 - Tue, Oct 6
Multiple Airlines Logo
12:59 pm - 11:57 pm
EYW
-
SJU
10h 58m
1 stop
Multiple Airlines Logo
4:39 pm - 9:24 am
SJU
-
EYW
16h 45m
1 stop
$268Multiple Airlines
Wed, Sep 30 - Sat, Oct 3
Multiple Airlines Logo
10:04 am - 11:57 pm
EYW
-
SJU
13h 53m
1 stop
Multiple Airlines Logo
4:39 pm - 11:21 am
SJU
-
EYW
18h 42m
1 stop
$271Multiple Airlines
Fri, Oct 2 - Tue, Oct 6
Multiple Airlines Logo
12:59 pm - 11:57 pm
EYW
-
SJU
10h 58m
1 stop
Multiple Airlines Logo
5:12 pm - 9:24 am
SJU
-
EYW
16h 12m
2 stops
$273Multiple Airlines
Mon, Jul 20 - Fri, Jul 24
American Airlines Logo
11:28 am - 3:12 pm
EYW
-
MHH
3h 44m
1 stop
American Airlines Logo
12:50 pm - 7:06 pm
MHH
-
EYW
6h 16m
1 stop
$555American Airlines
Tue, Aug 11 - Tue, Aug 18
American Airlines Logo
1:40 pm - 5:51 pm
EYW
-
NAS
4h 11m
1 stop
American Airlines Logo
2:36 pm - 6:31 pm
NAS
-
EYW
3h 55m
1 stop
$576American Airlines
Tue, Sep 29 - Fri, Oct 2
United Airlines Logo
2:15 pm - 1:33 pm
EYW
-
NAS
23h 18m
1 stop
United Airlines Logo
2:35 pm - 1:29 pm
NAS
-
EYW
22h 54m
1 stop
$893United Airlines
Sun, Aug 30 - Thu, Sep 3
United Airlines Logo
2:15 pm - 7:00 pm
EYW
-
EIS
28h 45m
2 stops
United Airlines Logo
9:45 am - 1:29 pm
EIS
-
EYW
27h 44m
2 stops
$1,305United Airlines
Thu, Jul 16 - Mon, Jul 20
WestJet Logo
2:24 pm - 2:30 pm
EYW
-
KIN
25h 06m
2 stops
WestJet Logo
3:30 pm - 5:23 pm
KIN
-
EYW
24h 53m
2 stops
$1,888WestJet
Booking Insights

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?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 5 days.

In the past 5 days, the cheapest round-trip tickets from Key West to Caribbean were found on American Airlines ($446) and United Airlines ($893).

Good to know

Cheapest flight$195
Flight from Key West to San Juan

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.
7.1
American AirlinesOverall score based on 11762 reviews
6.8Entertainment
7.2Comfort
6.4Food
7.5Boarding
7.9Crew
Airline reviews

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

2.0 MediocreWayne, Jun 2026
FLL - PHL
Read more American Airlines reviews

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

Absolutely terrible. They boarded the plane, supposedly realized they didn't refuel the plane or load the luggage so we sat as the gate inside the plane for over 2 hours while they supposedly did things that should have been done before having passengers board the planem

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Trash. Sat on the runway for 40 mins…missed connecting flight because of it now I’m stuck. Thanks…a whole fkn lot.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

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

Plane was extremely hot. Our flight were pushed back and changed several times. This was too excessive for one trip. I don’t feel like the passengers were priority.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports