$139 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 7/28. 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$539
Kingston
Kingston1 stop$739
Nassau
Nassau1 stop$539
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

Tue, Aug 18 - Tue, Aug 25
Multiple Airlines Logo
1:14 pm - 12:56 am
EYW
-
SJU
11h 42m
1 stop
Multiple Airlines Logo
5:37 pm - 12:04 pm
SJU
-
EYW
18h 27m
1 stop
$268Multiple Airlines
Thu, Jul 30 - Thu, Aug 13
Multiple Airlines Logo
11:04 am - 12:41 am
EYW
-
SJU
13h 37m
1 stop
Multiple Airlines Logo
10:48 pm - 11:27 am
SJU
-
EYW
12h 39m
1 stop
$284Multiple Airlines
Fri, Oct 30 - Sun, Nov 1
Multiple Airlines Logo
10:59 am - 5:37 pm
EYW
-
SJU
6h 38m
1 stop
Multiple Airlines Logo
6:31 pm - 10:19 am
SJU
-
EYW
16h 48m
1 stop
$323Multiple Airlines
Thu, Jul 30 - Thu, Aug 13
Multiple Airlines Logo
11:04 am - 12:41 am
EYW
-
SJU
13h 37m
1 stop
Multiple Airlines Logo
6:00 am - 9:41 am
SJU
-
EYW
27h 41m
2 stops
$346Multiple Airlines
Tue, Aug 18 - Tue, Aug 25
Multiple Airlines Logo
1:14 pm - 9:19 am
EYW
-
SJU
20h 05m
2 stops
Multiple Airlines Logo
5:37 pm - 11:06 am
SJU
-
EYW
17h 29m
1 stop
$363Multiple Airlines
Fri, Oct 30 - Sun, Nov 1
American Airlines Logo
5:28 pm - 10:22 pm
EYW
-
SJU
4h 54m
1 stop
American Airlines Logo
8:25 am - 6:45 pm
SJU
-
EYW
11h 20m
2 stops
$466American Airlines
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
8:09 pm - 9:43 am
EYW
-
SJU
13h 34m
1 stop
American Airlines Logo
1:38 pm - 7:39 pm
SJU
-
EYW
6h 01m
1 stop
$491American Airlines
Mon, Dec 14 - Fri, Dec 18
United Airlines Logo
2:30 pm - 1:48 pm
EYW
-
NAS
23h 18m
1 stop
United Airlines Logo
1:05 pm - 12:34 pm
NAS
-
EYW
23h 29m
1 stop
$981United Airlines
Mon, Dec 14 - Fri, Dec 18
United Airlines Logo
2:30 pm - 1:48 pm
EYW
-
NAS
23h 18m
1 stop
United Airlines Logo
1:05 pm - 12:34 pm
NAS
-
EYW
23h 29m
1 stop
$1,002United Airlines
Wed, Sep 2 - Wed, Sep 9
WestJet Logo
6:15 pm - 2:30 pm
EYW
-
KIN
45h 15m
2 stops
WestJet Logo
3:30 pm - 10:46 am
KIN
-
EYW
42h 16m
2 stops
$1,619WestJet
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 ($466) and United Airlines ($1,182).

Good to know

Cheapest flight

$139
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 11826 reviews
7.5Boarding
7.9Crew
6.4Food
6.8Entertainment
7.2Comfort
Airline reviews

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.

4.0 OkayHARMONY, Jul 2026
MCO - DFW
Read more American Airlines reviews

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.

American Airlines changed are gate no fewer than four times. Walking back and forth from one concourse to another was exhausting, especially after all the flight delays.

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

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