$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 9/9. 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$399
Kingston
Kingston1 stop$732
Nassau
Nassau1 stop$399
Kingston
Kingston1 stop$732

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

Mon, Aug 10 - Thu, Aug 13
Multiple Airlines Logo
1:11 pm - 12:41 am
EYW
-
SJU
11h 30m
1 stop
Multiple Airlines Logo
3:10 am - 11:27 am
SJU
-
EYW
8h 17m
1 stop
$297Multiple Airlines
Sun, Aug 9 - Thu, Aug 13
Multiple Airlines Logo
7:53 pm - 12:41 am
EYW
-
SJU
28h 48m
1 stop
Multiple Airlines Logo
10:48 pm - 11:27 am
SJU
-
EYW
12h 39m
1 stop
$363Multiple Airlines
Sun, Aug 9 - Thu, Aug 13
Multiple Airlines Logo
10:56 am - 4:49 pm
EYW
-
SJU
29h 53m
2 stops
Multiple Airlines Logo
10:48 pm - 11:27 am
SJU
-
EYW
12h 39m
1 stop
$390Multiple Airlines
Thu, Aug 6 - Mon, Aug 10
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
$399Breeze Airways
Mon, Aug 10 - Thu, Aug 13
Multiple Airlines Logo
7:27 pm - 12:41 am
EYW
-
SJU
29h 14m
2 stops
Multiple Airlines Logo
3:10 am - 11:27 am
SJU
-
EYW
8h 17m
1 stop
$419Multiple Airlines
Tue, Sep 15 - Thu, Sep 24
American Airlines Logo
7:47 pm - 11:00 am
EYW
-
SJU
15h 13m
1 stop
American Airlines Logo
10:16 am - 7:17 pm
SJU
-
EYW
9h 01m
1 stop
$446American Airlines
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
4:50 pm - 11:59 pm
EYW
-
SJU
7h 09m
1 stop
American Airlines Logo
6:00 am - 10:56 am
SJU
-
EYW
4h 56m
1 stop
$451American Airlines
Thu, Aug 6 - Mon, Aug 10
Delta Logo
7:40 am - 1:57 pm
EYW
-
NAS
6h 17m
1 stop
Delta Logo
1:16 pm - 7:57 pm
NAS
-
EYW
6h 41m
1 stop
$552Delta
Fri, Aug 28 - Tue, Sep 1
United Airlines Logo
2:15 pm - 11:28 am
EYW
-
NAS
21h 13m
1 stop
United Airlines Logo
2:35 pm - 1:29 pm
NAS
-
EYW
22h 54m
1 stop
$1,025United 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
4:00 pm - 3:42 pm
NAS
-
EYW
23h 42m
1 stop
$1,099United 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 Breeze Airways ($399) and American Airlines ($451).

Find deals

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 11809 reviews
7.9Crew
7.5Boarding
6.8Entertainment
6.4Food
7.2Comfort
Airline reviews

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.

6.0 GoodStewart, Jul 2026
MIA - BDA
Read more American Airlines reviews

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

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.

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

Key West (EYW)