$125 Find Cheap Flights from Key West to Caribbean - Compare and Save

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 8/28. 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$374
Kingston
Kingston1 stop$739
Nassau
Nassau1 stop$374
Kingston
Kingston1 stop$739

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

Fri, Aug 21 - Thu, Aug 27
Multiple Airlines Logo
1:11 pm - 12:56 am
EYW
-
SJU
11h 45m
1 stop
Multiple Airlines Logo
8:57 pm - 11:27 am
SJU
-
EYW
14h 30m
1 stop
$280Multiple Airlines
Mon, Aug 31 - Sat, Sep 5
Multiple Airlines Logo
1:11 pm - 12:56 am
EYW
-
SJU
11h 45m
1 stop
Multiple Airlines Logo
3:10 am - 11:25 am
SJU
-
EYW
8h 15m
1 stop
$291Multiple Airlines
Mon, Aug 31 - Sun, Sep 6
Multiple Airlines Logo
1:11 pm - 12:56 am
EYW
-
SJU
11h 45m
1 stop
Multiple Airlines Logo
6:35 am - 7:13 pm
SJU
-
EYW
12h 38m
2 stops
$324Multiple Airlines
Sat, Nov 14 - Sat, Nov 21
Multiple Airlines Logo
10:04 am - 12:57 am
EYW
-
SJU
13h 53m
1 stop
Multiple Airlines Logo
2:36 pm - 10:19 am
SJU
-
EYW
20h 43m
1 stop
$365Multiple Airlines
Wed, Sep 9 - Wed, Sep 16
Multiple Airlines Logo
10:04 am - 1:34 pm
EYW
-
SJU
27h 30m
2 stops
Multiple Airlines Logo
6:42 pm - 10:19 am
SJU
-
EYW
15h 37m
1 stop
$369Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Breeze Airways Logo
7:53 pm - 8:55 am
EYW
-
NAS
13h 02m
1 stop
Breeze Airways Logo
9:55 am - 12:34 pm
NAS
-
EYW
26h 39m
1 stop
$374Breeze Airways
Fri, Aug 21 - Thu, Aug 27
Multiple Airlines Logo
1:11 pm - 12:56 am
EYW
-
SJU
11h 45m
1 stop
Multiple Airlines Logo
3:48 pm - 10:27 am
SJU
-
EYW
18h 39m
2 stops
$386Multiple Airlines
Thu, Aug 27 - Mon, Aug 31
Multiple Airlines Logo
7:53 pm - 8:55 am
EYW
-
NAS
13h 02m
1 stop
Multiple Airlines Logo
4:00 pm - 12:34 pm
NAS
-
EYW
20h 34m
2 stops
$450Multiple Airlines
Fri, Oct 30 - Sun, Nov 1
American Airlines Logo
1:43 pm - 10:22 pm
EYW
-
SJU
8h 39m
1 stop
American Airlines Logo
10:32 am - 4:14 pm
SJU
-
EYW
6h 42m
1 stop
$466American Airlines
Wed, Sep 9 - Wed, Sep 16
American Airlines Logo
7:47 pm - 9:24 am
EYW
-
SJU
13h 37m
1 stop
American Airlines Logo
6:00 am - 7:17 pm
SJU
-
EYW
13h 17m
1 stop
$491American 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 5 days.

In the past 5 days, the cheapest round-trip tickets from Key West to Caribbean were found on American Airlines ($621) and United Airlines ($908).

Good to know

Cheapest flight

$125
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 11845 reviews
7.2Comfort
7.5Boarding
7.9Crew
6.8Entertainment
6.4Food
Airline reviews

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

10.0 ExcellentSergio, Jul 2026
MIA - DCA
Read more American Airlines reviews

Like all planes recently, entertainment is achieved by giving the patron free WiFi and letting them stream shows via the screen on a phone or tablet.

I thought American Airlines did well considering the adverse weather situation over July 21 and 22. I especially appreciated the consideration given to me when I got stuck in Miami on my way to Boston from Charleston, West Virginia. Thank you for providing a voucher for an overnight stay. Though it was only a few hours of sleep, it was very helpful. I was able to reschedule my medical appointment and got back to the Boston area on the 1st flight out of Miami as a standby passenger. It was very helpful that I was given number one priority on the standby list.

Quick flight. No time to stress over it. Over before it begins.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Not great. I understand delays happen due to weather and crew issues, but it was unacceptable that no agents were available at the counters inside the airport for customer service or help getting on a standby list. The app was not helpful either. I stood in line for an hour waiting for someone to show up at the gate to help me get on a standby flight. Customer care does not seem to be a priority.

As I said I never took the flight back from due to earlier delayed that prevented from taking the second trip back and nobody helped me to rebook from kayak

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

Would have been good to have the live TV outside of the continental United States as AA was promoting they are sponsors of the Fifa World Cup only for the live coverage to end.

Terrible check in experience in Miami airport by a so-called supervisor. Food came and they were picking up trash within 5 mins. Did not get fed again for about 6 hours. No chance to buy anything on board, horrible experience. Flight attendants have no control over passengers dropping off bags closer to the exit, not close to their seat.

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports