$147 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 3/2. 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$485
Kingston
Kingston1 stop$764
Nassau
Nassau1 stop$485
Kingston
Kingston1 stop$764

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

Tue, Mar 10 - Tue, Mar 17
Multiple Airlines Logo
1:01 pm - 11:10 am
EYW
-
SJU
22h 09m
1 stop
Multiple Airlines Logo
7:54 pm - 11:30 am
SJU
-
EYW
15h 36m
1 stop
$291Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
9:49 am - 3:31 pm
EYW
-
SJU
28h 42m
2 stops
Multiple Airlines Logo
6:00 am - 12:26 pm
SJU
-
EYW
7h 26m
1 stop
$319Multiple Airlines
Mon, Feb 23 - Fri, Feb 27
Multiple Airlines Logo
9:49 am - 2:25 am
EYW
-
SJU
15h 36m
1 stop
Multiple Airlines Logo
6:00 am - 12:26 pm
SJU
-
EYW
7h 26m
1 stop
$324Multiple Airlines
Wed, Jul 29 - Tue, Aug 4
American Airlines Logo
4:45 pm - 12:17 am
EYW
-
SJU
7h 32m
1 stop
American Airlines Logo
2:41 pm - 7:21 pm
SJU
-
EYW
4h 40m
1 stop
$386American Airlines
Wed, Jul 29 - Tue, Aug 4
American Airlines Logo
7:33 pm - 9:33 am
EYW
-
SJU
14h 00m
2 stops
American Airlines Logo
10:23 am - 7:21 pm
SJU
-
EYW
8h 58m
1 stop
$426American Airlines
Fri, Feb 27 - Fri, Mar 6
American Airlines Logo
1:55 pm - 11:34 pm
EYW
-
SJU
8h 39m
1 stop
American Airlines Logo
2:23 pm - 7:15 pm
SJU
-
EYW
5h 52m
1 stop
$446American Airlines
Wed, Jul 29 - Tue, Aug 4
American Airlines Logo
7:33 pm - 9:33 am
EYW
-
SJU
14h 00m
2 stops
American Airlines Logo
6:00 am - 4:12 pm
SJU
-
EYW
10h 12m
2 stops
$466American Airlines
Wed, Feb 18 - Tue, Feb 24
United Airlines Logo
6:35 pm - 1:53 pm
EYW
-
KIN
19h 18m
2 stops
United Airlines Logo
3:00 pm - 4:07 pm
KIN
-
EYW
25h 07m
2 stops
$975United Airlines
Sun, May 31 - Wed, Jun 3
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m
2 stops
United Airlines Logo
2:59 pm - 3:15 pm
KIN
-
EYW
47h 16m
2 stops
$4,826United Airlines
Sun, May 31 - Wed, Jun 3
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m
2 stops
United Airlines Logo
2:59 pm - 3:15 pm
KIN
-
EYW
47h 16m
2 stops
$5,097United Airlines
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 72 hours.

In the past 3 days, the cheapest round-trip tickets from Key West to Caribbean were found on American Airlines ($446) and Spirit Airlines ($491).

Find deals

Good to know

Cheapest flight$147
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.
7.2
American AirlinesOverall score based on 11254 reviews
6.4Food
8.0Crew
7.5Boarding
7.2Comfort
6.9Entertainment
Airline reviews

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

2.0 MediocreSalim, Feb 2026
JAX - PHL
Read more American Airlines reviews

Awful. Original flight was delayed 5 hours. Had to to take a connecting flight instead of direct. Had a 4 hour layover. I missed all of my morning meetings getting in 5 hours later than I was supposed to and had to change to take a later flight the next day to get them back in which cia time another $150.

On time on a day with lots of weather cancellations on other flights. Thank you for getting me home during a winter storm!

Don't change gate multiple times make people run across the airport. Announce delays in a timely manner. Have maintenance crew ready. Don't delay and keep passengers on the plane for 3 hrs. on tarmac.

The attendants were kind and helpful. A sugar-free drink would have been very welcome.

Little warm on the plane and delayed for an hour

UGH I HAD TO MISS MY FIRST FLIGHT TO TAMPA CAUSE OF THE 10 MINUTE DELAY OF THE ORLANDO TO MIAMI ONE SO THEY HAD ME GET ANOTHER TICKET. I AM NOT HAPPY AT ALL BECAUSE IT MADE ME MISS MY CONNECTING FLIGHT FROM TAMPA TO LONDON AND FORCED ME TO MISS A DAY AT MY ROOM IN THE UK.

Wish they didnt delay off-boarding for 10 minutes so i could connect to my flight from miami to tampa

It was fine. My connection in Charlotte to go to WPB was too late and I had to spend the night in the Charlotte Airport in the mini suites.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Key West (EYW)