$206 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 1/11. 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

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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$525
Kingston
Kingston1 stop$733
Nassau
Nassau1 stop$525
Kingston
Kingston1 stop$733

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, Nov 3 - Thu, Nov 13
Multiple Airlines Logo
8:55 am - 2:44 amEYW-SJU
16h 49m1 stop
Multiple Airlines Logo
7:30 am - 9:17 amSJU-EYW
26h 47m1 stop
$343Multiple Airlines
Find Deal
Mon, Nov 3 - Thu, Nov 13
Multiple Airlines Logo
11:11 am - 3:33 amEYW-SJU
15h 22m2 stops
Multiple Airlines Logo
7:30 am - 9:17 amSJU-EYW
26h 47m1 stop
$363Multiple Airlines
Find Deal
Wed, Oct 1 - Sun, Oct 5
Multiple Airlines Logo
10:47 am - 12:43 amEYW-SJU
37h 56m2 stops
Multiple Airlines Logo
9:07 am - 8:15 amSJU-EYW
23h 08m1 stop
$416Multiple Airlines
Find Deal
Mon, Nov 3 - Thu, Nov 13
Multiple Airlines Logo
6:36 pm - 3:12 pmEYW-SJU
19h 36m2 stops
Multiple Airlines Logo
9:49 pm - 1:30 pmSJU-EYW
16h 41m2 stops
$425Multiple Airlines
Find Deal
Mon, Nov 3 - Thu, Nov 13
Multiple Airlines Logo
6:36 pm - 3:12 pmEYW-SJU
19h 36m2 stops
Multiple Airlines Logo
10:57 am - 1:30 pmSJU-EYW
27h 33m3 stops
$430Multiple Airlines
Find Deal
Wed, Oct 1 - Mon, Oct 6
American Airlines Logo
6:17 pm - 12:47 pmEYW-SJU
18h 30m2 stops
American Airlines Logo
7:00 am - 7:22 pmSJU-EYW
12h 22m1 stop
$525American Airlines
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Sat, Nov 1 - Sat, Nov 8
American Airlines Logo
5:47 pm - 6:37 pmEYW-NAS
24h 50m1 stop
American Airlines Logo
7:49 am - 5:01 pmNAS-EYW
9h 12m1 stop
$525American Airlines
Find Deal
Thu, Oct 16 - Thu, Oct 23
JetBlue Logo
1:04 pm - 4:52 pmEYW-NAS
27h 48m2 stops
JetBlue Logo
6:00 pm - 12:09 pmNAS-EYW
18h 09m2 stops
$679JetBlue
Find Deal
Wed, Oct 1 - Mon, Oct 6
United Airlines Logo
3:12 pm - 12:34 pmEYW-SJU
21h 22m2 stops
United Airlines Logo
4:55 pm - 2:29 pmSJU-EYW
21h 34m2 stops
$794United Airlines
Find Deal
Wed, Oct 1 - Mon, Oct 6
United Airlines Logo
3:12 pm - 12:34 pmEYW-SJU
21h 22m2 stops
United Airlines Logo
4:55 pm - 2:29 pmSJU-EYW
21h 34m2 stops
$808United Airlines
Find Deal
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 ($525) and JetBlue ($679).

Good to know

Low seasonApril
Cheapest flight$206
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly and prices are also 21% lower on average.
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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $404 on average. Morning departures are around 10% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $448.

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 10000 reviews
8.0Crew
6.4Food
7.5Boarding
7.2Comfort
6.9Entertainment
Airline reviews

Lost bag and 2 days no word leaving for cruise no clothes or stuff

2.0 MediocreYvonne, Sep 2025PBI - ORD
Read more American Airlines reviews

Lost bag and 2 days no word leaving for cruise no clothes or stuff

We will be writing a long, detailed letter to corporate about our awful experience with American airlines.

Internet was a bit expensive and did not work ask that week otherwise a good flight

Food was ok, but not as good as I have had before on AA.

Pretty good. The food was just mediocre, the boarding and crew were good.

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

The plane was broken so we had to change planes.

Food was terrible, all served at once, poor quality . Wine and bread offered only once.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

Everything you need to know for your flight to Caribbean

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