$233 Find Cheap Flights from Key West to Caribbean Islands

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 Islands departing on 12/23. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Key West to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Key West to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Nassau
Nassau1 stop$505
Nassau
Nassau1 stop$505

Book Cheap Key West to Caribbean Islands 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 Islands 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 Islands

Wed, Oct 1 - Mon, Oct 6
American Airlines Logo
11:25 am - 6:14 pmEYW-SJU
6h 49m1 stop
American Airlines Logo
7:05 pm - 2:43 pmSJU-EYW
19h 38m2 stops
$365American Airlines
Find Deal
Sat, Sep 13 - Sat, Sep 20
American Airlines Logo
11:25 am - 11:10 amEYW-NAS
23h 45m1 stop
American Airlines Logo
10:26 am - 1:29 pmNAS-EYW
3h 03m1 stop
$505American Airlines
Find Deal
Wed, Aug 13 - Sun, Aug 17
American Airlines Logo
1:52 pm - 6:15 pmEYW-SJU
4h 23m1 stop
American Airlines Logo
6:00 am - 10:53 amSJU-EYW
4h 53m1 stop
$525American Airlines
Find Deal
Thu, Aug 14 - Mon, Aug 18
American Airlines Logo
4:49 pm - 11:09 amEYW-SJU
18h 20m2 stops
American Airlines Logo
5:15 pm - 12:32 pmSJU-EYW
19h 17m2 stops
$535American Airlines
Find Deal
Thu, Sep 4 - Mon, Sep 8
American Airlines Logo
1:59 pm - 5:58 pmEYW-NAS
3h 59m1 stop
American Airlines Logo
10:26 am - 6:59 pmNAS-EYW
8h 33m1 stop
$535American Airlines
Find Deal
Sat, Aug 16 - Sat, Aug 23
American Airlines Logo
12:50 pm - 10:56 pmEYW-SJU
10h 06m1 stop
American Airlines Logo
12:00 pm - 5:23 pmSJU-EYW
5h 23m1 stop
$545American Airlines
Find Deal
Wed, Aug 13 - Sat, Aug 16
 Logo
10:02 am - 4:42 pmEYW-SJU
30h 40m3 stops
 Logo
2:11 am - 1:07 pmSJU-EYW
10h 56m1 stop
Sat, Aug 16 - Sat, Aug 23
American Airlines Logo
4:49 pm - 11:09 amEYW-SJU
18h 20m2 stops
American Airlines Logo
7:05 pm - 11:58 amSJU-EYW
16h 53m2 stops
$560American Airlines
Find Deal
Thu, Aug 14 - Sun, Aug 17
 Logo
10:02 am - 12:56 amEYW-SJU
14h 54m1 stop
 Logo
2:11 am - 1:07 pmSJU-EYW
10h 56m1 stop
Thu, Aug 14 - Mon, Aug 18
United Airlines Logo
2:22 pm - 11:54 pmEYW-SJU
33h 32m2 stops
United Airlines Logo
7:45 am - 2:25 pmSJU-EYW
30h 40m2 stops
$1,229United Airlines
Find Deal
Booking Insights

KAYAK's insights & trends for Key West to Caribbean Islands flights

Get data-powered insights and trends into flights from Key West to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Key West to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $433, prices are generally cheapest when you fly direct.


Good to know

Low seasonSeptember
Cheapest flight$233
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Key West to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Key West to Caribbean Islands?

    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 Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Key West to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Key West to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands?

    The cheapest time of day to fly to Caribbean Islands 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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Key West to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Key West to Caribbean Islands? 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
6.5Food
8.0Crew
7.5Boarding
6.9Entertainment
7.2Comfort
Airline reviews

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.

8.0 ExcellentKimber, Jul 2025JAX - DFW
Read more American Airlines reviews

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.

I was late from Jacksonville, FL but the limited interaction I had with the Philly crew was great.

The delays and cancellations kept me stuck in Miami for an additional 24 hours, and the whole thing seemed extremely disorganized

The chicken adobo was a little too spicy but good otherwise. My personal opinion. Movie selection could be improved, too many horror movies. Could add a few more chick flicks! The flight was bumpy at times. We arrived a little early too! Flight attendants friendly.

really bad they refused to check in luggages that I had purchased, even showing them the transaction receipt from british airways app the staff in miami was MEDIOCRE

The flight to Tokyo AA61 took off about two hours late, but then had to turn back. By that time the crew had to be replaced. Then they kept promising to take off in an hour, then in 3, then switch to the next day.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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