$171 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 5/29. 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$494
Kingston
Kingston1 stop$533
Nassau
Nassau1 stop$494
Kingston
Kingston1 stop$533

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

Sat, Mar 28 - Sat, Apr 4
Multiple Airlines Logo
3:33 pm - 10:10 am
EYW
-
SJU
18h 37m
1 stop
Multiple Airlines Logo
8:57 am - 10:21 am
SJU
-
EYW
25h 24m
1 stop
$332Multiple Airlines
Wed, Apr 8 - Thu, Apr 9
Multiple Airlines Logo
12:25 pm - 6:55 pm
EYW
-
SJU
6h 30m
1 stop
Multiple Airlines Logo
1:45 am - 12:26 pm
SJU
-
EYW
10h 41m
1 stop
$334Multiple Airlines
Sat, Mar 28 - Sat, Apr 4
Multiple Airlines Logo
3:33 pm - 10:10 am
EYW
-
SJU
18h 37m
1 stop
Multiple Airlines Logo
6:00 am - 9:06 am
SJU
-
EYW
27h 06m
2 stops
$349Multiple Airlines
Wed, Apr 8 - Thu, Apr 9
Spirit Airlines Logo
12:25 pm - 6:55 pm
EYW
-
SJU
6h 30m
1 stop
Spirit Airlines Logo
1:45 am - 1:37 pm
SJU
-
EYW
11h 52m
2 stops
$350Spirit Airlines
Thu, Aug 13 - Wed, Aug 19
Multiple Airlines Logo
11:04 am - 12:47 am
EYW
-
SJU
13h 43m
2 stops
Multiple Airlines Logo
10:50 am - 11:25 am
SJU
-
EYW
24h 35m
1 stop
$367Multiple Airlines
Wed, Apr 1 - Wed, Apr 8
Multiple Airlines Logo
11:51 am - 12:02 am
EYW
-
SJU
12h 11m
1 stop
Multiple Airlines Logo
8:47 pm - 3:42 pm
SJU
-
EYW
18h 55m
1 stop
$370Multiple Airlines
Wed, Apr 8 - Thu, Apr 9
Spirit Airlines Logo
12:25 pm - 8:53 am
EYW
-
SJU
20h 28m
2 stops
Spirit Airlines Logo
1:45 am - 1:37 pm
SJU
-
EYW
11h 52m
2 stops
$385Spirit Airlines
Fri, Apr 24 - Wed, Apr 29
American Airlines Logo
3:58 pm - 8:27 pm
EYW
-
NAS
4h 29m
1 stop
American Airlines Logo
12:00 pm - 10:58 pm
NAS
-
EYW
10h 58m
1 stop
$521American Airlines
Wed, Mar 25 - Wed, Apr 1
American Airlines Logo
3:56 pm - 3:30 pm
EYW
-
MHH
23h 34m
1 stop
American Airlines Logo
1:04 pm - 7:12 pm
MHH
-
EYW
6h 08m
1 stop
$531American Airlines
Mon, Apr 13 - Sat, Apr 18
United Airlines Logo
4:38 pm - 1:52 pm
EYW
-
KIN
46h 14m
2 stops
United Airlines Logo
2:59 pm - 3:57 pm
KIN
-
EYW
47h 58m
2 stops
$1,083United 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 ($406) and Spirit Airlines ($458).

Good to know

Cheapest flight$174
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 11375 reviews
6.4Food
7.5Boarding
6.9Entertainment
7.2Comfort
8.0Crew
Airline reviews

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

8.0 ExcellentLinda, Mar 2026
MCO - CLT
Read more American Airlines reviews

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Everything was good. Flight was very full so crew was busy. After we boarded and plane pulled away from the gate, we were delayed about 40 minutes- sitting on the runway - due to weather en route or at the destination. While weather is not the fault of the airline- it’s terrible to sit on a plane and not moving.

The smell from the bathroom kept wafting through the cabin. It made people sick.

Waited for oxygen tanks for 30 minutes after boarding was complete.

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!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports