$221 Find Cheap Flights from Key West to Caribbean - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Key West to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Nassau
Nassau1 stop$440
Kingston
Kingston2 stops$1,117
Nassau
Nassau1 stop$440
Kingston
Kingston2 stops$1,117

Book Cheap Key West to Caribbean Plane Tickets

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Key West to Caribbean

Mon, Dec 7 - Sun, Dec 13
Multiple Airlines Logo
10:59 am - 1:07 amEYW  Key West-SJU San Juan Luis Munoz Marin Intl
13h 08m2 stops Orlando Atlanta Hartsfield-Jackson
Multiple Airlines Logo
8:44 pm - 10:19 amSJU  San Juan Luis Munoz Marin Intl-EYW Key West
14h 35m1 stop Orlando
$400Multiple Airlines
Fri, Nov 27 - Mon, Dec 7
Multiple Airlines Logo
12:59 pm - 9:49 pmEYW  Key West-SJU San Juan Luis Munoz Marin Intl
7h 50m1 stop Tampa
Multiple Airlines Logo
5:16 pm - 10:19 amSJU  San Juan Luis Munoz Marin Intl-EYW Key West
18h 03m2 stops Philadelphia Orlando
$404Multiple Airlines
Fri, Nov 27 - Mon, Dec 7
Multiple Airlines Logo
12:59 pm - 9:49 pmEYW  Key West-SJU San Juan Luis Munoz Marin Intl
7h 50m1 stop Tampa
Multiple Airlines Logo
4:04 pm - 10:19 amSJU  San Juan Luis Munoz Marin Intl-EYW Key West
19h 15m1 stop Orlando
$416Multiple Airlines
Mon, Dec 7 - Sun, Dec 13
Multiple Airlines Logo
10:59 am - 10:37 amEYW  Key West-SJU San Juan Luis Munoz Marin Intl
22h 38m1 stop Orlando
Multiple Airlines Logo
8:44 pm - 10:19 amSJU  San Juan Luis Munoz Marin Intl-EYW Key West
14h 35m1 stop Orlando
$436Multiple Airlines
Sat, Nov 21 - Wed, Nov 25
Multiple Airlines Logo
10:04 am - 9:25 amEYW  Key West-NAS Nassau Intl
23h 21m1 stop Tampa
Multiple Airlines Logo
9:25 am - 9:39 amNAS  Nassau Intl-EYW Key West
24h 14m1 stop Tampa
$440Multiple Airlines
Sat, Nov 28 - Mon, Dec 7
Multiple Airlines Logo
1:09 pm - 9:49 pmEYW  Key West-SJU San Juan Luis Munoz Marin Intl
7h 40m1 stop Tampa
Multiple Airlines Logo
6:00 am - 10:19 amSJU  San Juan Luis Munoz Marin Intl-EYW Key West
29h 19m2 stops Baltimore/Washington Orlando
$444Multiple Airlines
Thu, Jan 21 - Tue, Jan 26
Multiple Airlines Logo
6:25 pm - 8:35 pmEYW  Key West-PUJ Punta Cana
25h 10m1 stop Orlando Sanford Intl
Multiple Airlines Logo
6:42 pm - 10:39 amPUJ  Punta Cana-EYW Key West
16h 57m2 stops San Juan Luis Munoz Marin Intl Orlando
$459Multiple Airlines
Sat, Nov 28 - Mon, Dec 7
Multiple Airlines Logo
1:09 pm - 9:49 pmEYW  Key West-SJU San Juan Luis Munoz Marin Intl
7h 40m1 stop Tampa
Multiple Airlines Logo
8:44 pm - 10:19 amSJU  San Juan Luis Munoz Marin Intl-EYW Key West
14h 35m1 stop Orlando
$460Multiple Airlines
Tue, Jan 26 - Tue, Feb 2
American Airlines Logo
6:26 pm - 2:10 pmEYW  Key West-STT Saint Thomas Island Cyril E King
18h 44m2 stops Charlotte Douglas Miami
American Airlines Logo
5:04 pm - 1:08 pmSTT  Saint Thomas Island Cyril E King-EYW Key West
21h 04m2 stops Miami Charlotte Douglas
$498American Airlines
Tue, Jan 26 - Tue, Feb 2
American Airlines Logo
6:26 pm - 1:18 pmEYW  Key West-STT Saint Thomas Island Cyril E King
17h 52m1 stop Charlotte Douglas
American Airlines Logo
5:04 pm - 1:08 pmSTT  Saint Thomas Island Cyril E King-EYW Key West
21h 04m2 stops Miami Charlotte Douglas
$498American Airlines
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?

In the past 5 days, the cheapest round-trip tickets from Key West to Caribbean were found on American Airlines ($498) and Delta ($875).

Find deals

Good to know

Cheapest flight

$221
Flight from Key West to Nassau

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.

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.
7.0
American AirlinesOverall score based on 12225 reviews
7.2Comfort
6.8Entertainment
7.4Boarding
7.9Crew
6.4Food
Airline reviews

Im reviewing a flight that hasn’t even taken off because it’s been delayed for almost 5 hours. Amazing. Great time. No vouchers. Nothing. Thanks.

2.0 MediocreMichael, Nov 2026
Read more American Airlines reviews

Im reviewing a flight that hasn’t even taken off because it’s been delayed for almost 5 hours. Amazing. Great time. No vouchers. Nothing. Thanks.

The old CRJ700's are rough, slightly larger regional jet would have been nice.

Seats were very tight for a 17 hour flight. Baby cried for 15 out of 17 hours.

Good flight, excellent personnel; poor comfort, small seats, big cost.

This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.

Cabin was bone dry, no humidity whatsoever, and pretty warm; and beverage service didn't start for at least an hour. I had to go to the back for water and the FAs tried telling me it was always this way for all Miami flights, which is complete nonsense. Avoid the MAX8 like the plague.

Im sitting here waiting over an hour for my golf clubs

Flight was 2+ hours delayed and they “misplaced” all 3 of our checked-in bags.

Overall, really good experience, on time and the comfort was there. Wi-Fi was easy to connect

I have never been assaulted they way I was today in Charlotte - shame on American

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