$147 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 2/20. 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$468
Kingston
Kingston2 stops$4,826
Nassau
Nassau1 stop$468
Kingston
Kingston2 stops$4,826

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

Fri, Feb 27 - Fri, Mar 6
Multiple Airlines Logo
1:06 pm - 12:43 am
EYW
-
SJU
10h 37m
1 stop
Multiple Airlines Logo
6:00 am - 12:26 pm
SJU
-
EYW
7h 26m
1 stop
$289Multiple Airlines
Sat, Feb 7 - Wed, Feb 11
Multiple Airlines Logo
10:49 am - 3:12 pm
EYW
-
SJU
27h 23m
2 stops
Multiple Airlines Logo
6:00 am - 9:06 am
SJU
-
EYW
28h 06m
1 stop
$355Multiple Airlines
Thu, Feb 19 - Sat, Feb 21
Multiple Airlines Logo
9:46 am - 1:24 am
EYW
-
SJU
14h 38m
2 stops
Multiple Airlines Logo
3:53 am - 9:06 am
SJU
-
EYW
6h 13m
1 stop
$378Multiple Airlines
Thu, Feb 19 - Sat, Feb 21
Multiple Airlines Logo
9:46 am - 2:53 am
EYW
-
SJU
16h 07m
1 stop
Multiple Airlines Logo
3:53 am - 9:06 am
SJU
-
EYW
6h 13m
1 stop
$394Multiple Airlines
Fri, Feb 27 - Thu, Mar 5
Spirit Airlines Logo
2:25 pm - 1:37 am
EYW
-
SJU
10h 12m
2 stops
Spirit Airlines Logo
2:59 am - 1:30 pm
SJU
-
EYW
11h 31m
2 stops
$415Spirit Airlines
Fri, Feb 27 - Fri, Mar 6
American Airlines Logo
1:55 pm - 9:34 pm
EYW
-
SJU
6h 39m
1 stop
American Airlines Logo
2:23 pm - 7:15 pm
SJU
-
EYW
5h 52m
1 stop
$426American Airlines
Fri, Feb 27 - Thu, Mar 5
Spirit Airlines Logo
2:25 pm - 6:58 pm
EYW
-
SJU
27h 33m
3 stops
Spirit Airlines Logo
2:59 am - 1:30 pm
SJU
-
EYW
11h 31m
2 stops
$457Spirit Airlines
Sun, Mar 15 - Sun, Mar 22
American Airlines Logo
7:42 pm - 10:56 am
EYW
-
SJU
15h 14m
1 stop
American Airlines Logo
7:11 am - 7:12 pm
SJU
-
EYW
12h 01m
1 stop
$466American Airlines
Wed, May 13 - Sat, May 16
United Airlines Logo
4:00 pm - 2:57 pm
EYW
-
NAS
22h 57m
1 stop
United Airlines Logo
3:59 pm - 3:07 pm
NAS
-
EYW
23h 08m
1 stop
$751United Airlines
Sun, May 31 - Wed, Jun 3
United Airlines Logo
4:05 pm - 1:54 pm
EYW
-
KIN
46h 49m
2 stops
United Airlines Logo
2:59 pm - 3:15 pm
KIN
-
EYW
47h 16m
2 stops
$4,826United Airlines
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 $333, prices are generally cheapest when you fly direct.

Find deals

Good to know

Low seasonApril
Cheapest flight$147
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Key West (EYW)