$158 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 8/22. 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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 20% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals
Useful Info
Flights Deals

Best Caribbean Flight Deals from Key West

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Nassau
Nassau1 stop$461
Nassau
Nassau1 stop$461

Cheap Flights from Key West to Caribbean

 
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

Wed, Oct 1 - Mon, Oct 6
American Airlines Logo
3:45 pm - 11:11 amEYW-SJU
19h 26m2 stops
American Airlines Logo
6:30 am - 4:29 pmSJU-EYW
9h 59m1 stop
$365American Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
Silver Airways Logo
8:45 am - 12:55 pmEYW-MHH
4h 10m1 stop
Silver Airways Logo
1:40 pm - 6:05 pmMHH-EYW
4h 25m1 stop
$369Silver Airways
Find Deal
Thu, Jul 10 - Sat, Jul 12
American Airlines Logo
7:51 pm - 11:04 amEYW-SJU
15h 13m1 stop
American Airlines Logo
6:04 am - 10:57 amSJU-EYW
4h 53m1 stop
$430American Airlines
Find Deal
Wed, Jul 9 - Wed, Jul 16
American Airlines Logo
7:51 pm - 1:35 pmEYW-NAS
17h 44m1 stop
American Airlines Logo
10:36 am - 7:21 pmNAS-EYW
8h 45m1 stop
$461American Airlines
Find Deal
Sat, Jul 26 - Sat, Aug 2
American Airlines Logo
11:39 am - 9:46 amEYW-NAS
22h 07m1 stop
American Airlines Logo
10:36 am - 7:21 pmNAS-EYW
8h 45m1 stop
$475American Airlines
Find Deal
Thu, Jul 31 - Mon, Aug 4
Delta Logo
7:00 am - 3:52 pmEYW-NAS
8h 52m1 stop
Delta Logo
1:13 pm - 7:49 pmNAS-EYW
6h 36m1 stop
$476Delta
Find Deal
Thu, Jun 26 - Sun, Jun 29
 Logo
10:12 am - 1:31 amEYW-SJU
15h 19m1 stop
 Logo
2:36 am - 1:17 pmSJU-EYW
10h 41m1 stop
Thu, Jun 26 - Sun, Jun 29
 Logo
10:12 am - 1:31 amEYW-SJU
15h 19m1 stop
 Logo
2:36 am - 9:22 amSJU-EYW
30h 46m3 stops
Wed, Oct 1 - Sun, Oct 5
United Airlines Logo
8:45 am - 11:57 pmEYW-SJU
15h 12m2 stops
United Airlines Logo
1:05 am - 8:00 amSJU-EYW
30h 55m2 stops
$714United Airlines
Find Deal
Wed, Oct 1 - Mon, Oct 6
United Airlines Logo
6:45 pm - 2:44 pmEYW-SJU
43h 59m3 stops
United Airlines Logo
4:55 pm - 6:05 pmSJU-EYW
49h 10m2 stops
$885United Airlines
Find Deal
Useful Info

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 ($365) and Silver Airways ($369).


Good to know

Cheapest flight$158
Flight from Key West to Marsh Harbour

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.

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
6.5Food
7.2Comfort
6.9Entertainment
7.5Boarding
Airline reviews

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

2.0 MediocreJose David, Jun 2025MIA - DTW
Read more American Airlines reviews

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.

Uncomfortable seats and flight attendant was rude as she insisted on waking up my husband to ask him if he wanted a drink. When he said that he was sleeping, she replied “without an attitude “. He was seated at 8c

No food/snack served during the flight. Crew wasn’t interested at all. Flew American First but flying low cost with Ryanair is even better

Crew professional. Easy bag drop off. On time. Good entertainment.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.