$189 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 11/26. 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

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$473
Kingston
Kingston2 stops$524
Nassau
Nassau1 stop$473
Kingston
Kingston2 stops$524

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, Feb 18 - Sun, Feb 22
American Airlines Logo
7:00 am - 6:00 pmEYW-SJU
10h 00m1 stop
American Airlines Logo
10:57 am - 4:43 pmSJU-EYW
6h 46m1 stop
$365American Airlines
Find Deal
Mon, Jan 5 - Thu, Jan 22
Multiple Airlines Logo
2:30 pm - 11:46 amEYW-SJU
20h 16m1 stop
Multiple Airlines Logo
10:58 am - 9:09 amSJU-EYW
23h 11m1 stop
$366Multiple Airlines
Find Deal
Mon, Jan 5 - Wed, Jan 21
Multiple Airlines Logo
2:30 pm - 11:46 amEYW-SJU
20h 16m1 stop
Multiple Airlines Logo
3:55 am - 9:06 amSJU-EYW
6h 11m1 stop
$372Multiple Airlines
Find Deal
Mon, Jan 5 - Thu, Jan 22
American Airlines Logo
8:09 pm - 10:48 amEYW-SJU
13h 39m1 stop
American Airlines Logo
11:38 am - 9:47 pmSJU-EYW
11h 09m2 stops
$405American Airlines
Find Deal
Mon, Jan 5 - Thu, Jan 22
Spirit Airlines Logo
2:30 pm - 10:05 pmEYW-SJU
6h 35m1 stop
Spirit Airlines Logo
12:10 pm - 1:30 pmSJU-EYW
26h 20m3 stops
$463Spirit Airlines
Find Deal
Mon, Jan 5 - Thu, Jan 22
Spirit Airlines Logo
2:30 pm - 2:20 pmEYW-SJU
22h 50m3 stops
Spirit Airlines Logo
12:10 pm - 1:30 pmSJU-EYW
26h 20m3 stops
$476Spirit Airlines
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Wed, Nov 26 - Wed, Dec 3
United Airlines Logo
3:00 pm - 9:00 pmEYW-SJU
29h 00m2 stops
United Airlines Logo
5:50 pm - 3:24 pmSJU-EYW
46h 34m2 stops
$1,096United Airlines
Find Deal
Wed, Nov 26 - Wed, Dec 3
JetBlue Logo
12:49 pm - 8:44 amEYW-NAS
19h 55m2 stops
JetBlue Logo
1:31 pm - 11:55 amNAS-EYW
22h 24m2 stops
$1,202JetBlue
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Tue, Dec 30 - Fri, Jan 2
United Airlines Logo
4:08 pm - 9:00 pmEYW-SJU
27h 52m1 stop
United Airlines Logo
10:15 am - 3:48 pmSJU-EYW
30h 33m1 stop
$1,223United Airlines
Find Deal
Mon, Dec 29 - Thu, Jan 1
JetBlue Logo
1:12 pm - 11:56 pmEYW-SJU
9h 44m1 stop
JetBlue Logo
2:05 am - 12:17 pmSJU-EYW
11h 12m1 stop
$1,365JetBlue
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 $319, prices are generally cheapest when you fly direct.

Good to know

Cheapest flight$189
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 11030 reviews
7.2Comfort
6.9Entertainment
6.4Food
8.0Crew
7.5Boarding
Airline reviews

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

2.0 Mediocre603, Oct 2025MIA - GRU
Read more American Airlines reviews

My flight was delayed for 17hs because the pilot forgot his passport!!! What a joke. AA used to be a great airline, now I have to think twice before flying with them again.

We had 3 flights. 1 & 2 were on the same plane but we had to de-board just to re-board 30 mins later. That may have been due to a crew change though. Our 3rd flight had a couple “maintenance” issues that held us up. They were quickly resolved but it took forever for someone to bring the paperwork needed so we could leave. Apparently there was a computer glitch so a driver had to bring a physical copy. It delayed us about 1 1/2 hrs. The flights themselves were smooth & no problems. For boarding, I don’t know why they don’t start with the back of the plane & move forward. It would eliminate the back up from people trying to find their seats & put their bags in the overhead bins. Unless you’re on an overseas flight, there is no food, you get a beverage & either a small bag of pretzels or a biscuit cookie. Take your own food or snacks of you want something more.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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