$233+ Cheap flights from Key West (EYW) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Dec 8 — Dec 151
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Key West to CaribbeanExplore the most affordable flight options available from Key West to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 8, 2026.
Explore the most affordable flight options available from Key West to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:04 am -
2 stops13h 55m
Sun 11/2210:54 pm -
1 stop14h 25m
Deal found 11/3![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/710:59 am -
2 stops13h 08m
Sun 12/138:44 pm -
1 stop14h 35m
Deal found 11/8![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2712:59 pm -
1 stop7h 50m
Mon 12/75:16 pm -
2 stops18h 03m
Deal found 11/8![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:59 am -
1 stop6h 22m
Sun 11/156:15 am -
2 stops29h 04m
Deal found 11/4![Multiple Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:04 am -
1 stop23h 21m
Wed 11/259:25 am -
1 stop24h 14m
Deal found 11/5![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/281:09 pm -
1 stop7h 40m
Mon 12/76:00 am -
2 stops29h 19m
Deal found 11/8![Multiple Airlines logo]()
$444
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:00 pm -
1 stop15h 17m
Sat 12/196:44 pm -
2 stops18h 59m
Deal found 11/6![American Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2910:59 am -
1 stop14h 25m
Sun 12/63:03 pm -
2 stops20h 16m
Deal found 11/8![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:59 am -
1 stop5h 16m
Mon 12/219:25 am -
1 stop25h 56m
Deal found 11/7![Multiple Airlines logo]()
$565
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:35 pm -
2 stops29h 39m
Mon 12/284:50 pm -
1 stop18h 29m
Deal found 11/8![Multiple Airlines logo]()
$584
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:04 am -
1 stop22h 50m
Thu 11/2610:16 am -
2 stops26h 03m
Deal found 11/7![Multiple Airlines logo]()
$613
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2210:15 am -
1 stop6h 58m
Tue 12/297:13 pm -
1 stop15h 32m
Deal found 11/7![American Airlines logo]()
$777
Best flights from Key West to CaribbeanDiscover carefully curated flight deals from Key West to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 8, 2026.
Discover carefully curated flight deals from Key West to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated November 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:04 am -
1 stop23h 21m
Wed 11/259:25 am -
1 stop24h 14m
Deal found 11/5![Multiple Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/266:26 pm -
1 stop17h 52m
Tue 2/25:04 pm -
2 stops21h 04m
Deal found 11/6![American Airlines logo]()
$498
This Breeze Airways deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2612:59 pm -
1 stop24h 51m
Wed 3/33:50 pm -
1 stop20h 36m
Deal found 11/3![Breeze Airways logo]()
$516
This Delta deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1911:43 am -
2 stops13h 31m
Mon 11/237:02 am -
2 stops13h 58m
Deal found 11/5![Delta logo]()
$875
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/23:15 pm -
1 stop23h 12m
Fri 2/53:35 pm -
1 stop20h 41m
Deal found 11/4![United Airlines logo]()
$882
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:00 pm -
1 stop15h 17m
Sat 12/196:44 pm -
2 stops18h 59m
Deal found 11/6![American Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:59 am -
1 stop5h 16m
Mon 12/219:25 am -
1 stop25h 56m
Deal found 11/7![Multiple Airlines logo]()
$565
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/269:55 am -
1 stop5h 03m
Wed 3/36:20 pm -
2 stops20h 17m
Deal found 11/3![American Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2910:59 am -
1 stop14h 25m
Sun 12/63:03 pm -
1 stop21h 16m
Deal found 11/8![Multiple Airlines logo]()
$572
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:04 am -
1 stop22h 50m
Thu 11/2610:16 am -
2 stops26h 03m
Deal found 11/7![Multiple Airlines logo]()
$613
This American Airlines deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/259:58 am -
1 stop5h 09m
Thu 1/2812:57 pm -
1 stop7h 23m
Deal found 11/8![American Airlines logo]()
$624
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/410:59 am -
2 stops55h 01m
Mon 2/1512:40 pm -
1 stop23h 56m
Deal found 11/8![Multiple Airlines logo]()
$674
This United Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:05 pm -
1 stop8h 31m
Tue 12/82:05 am -
1 stop13h 31m
Deal found 11/7![United Airlines logo]()
$906
This United Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/192:50 pm -
1 stop8h 46m
Sun 11/222:05 am -
1 stop12h 47m
Deal found 11/4![United Airlines logo]()
$926
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2210:15 am -
1 stop6h 58m
Tue 12/297:13 pm -
1 stop15h 32m
Deal found 11/7![American Airlines logo]()
$777
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/14:09 pm -
1 stop23h 13m
Thu 2/43:35 pm -
1 stop23h 47m
Deal found 11/6![United Airlines logo]()
$943
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2810:23 am -
1 stop10h 15m
Sun 12/1311:34 am -
1 stop8h 56m
Deal found 11/7![American Airlines logo]()
$794
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/207:18 pm -
1 stop14h 04m
Sun 12/275:47 pm -
1 stop15h 58m
Deal found 11/5![American Airlines logo]()
$802
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2811:25 am -
1 stop21h 13m
Sat 12/123:11 pm -
1 stop5h 16m
Deal found 11/3![American Airlines logo]()
$813
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:18 am -
1 stop4h 33m
Thu 11/264:48 pm -
1 stop19h 07m
Deal found 11/7![American Airlines logo]()
$825
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/175:56 pm -
2 stops17h 31m
Mon 12/217:45 am -
1 stop9h 41m
Deal found 11/7![American Airlines logo]()
$881
This United Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/1412:05 pm -
2 stops24h 51m
Sat 12/193:35 pm -
3 stops45h 32m
Deal found 11/6![United Airlines logo]()
$1,567
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/68:02 pm -
1 stop14h 56m
Sat 3/135:05 pm -
1 stop22h 33m
Deal found 11/5![American Airlines logo]()
$896
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/214:58 pm -
1 stop4h 56m
Wed 11/257:30 am -
2 stops8h 34m
Deal found 11/5![American Airlines logo]()
$956
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1910:22 am -
1 stop4h 29m
Mon 11/237:19 pm -
2 stops18h 18m
Deal found 11/5![American Airlines logo]()
$978
This Mytrip deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/65:30 pm -
2 stops19h 15m
Sat 3/1311:45 am -
3 stops29h 15m
Deal found 11/5![Multiple Airlines logo]()
$2,441
This American Airlines deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/287:18 pm -
2 stops18h 19m
Mon 1/46:44 pm -
1 stop16h 01m
Deal found 11/5![American Airlines logo]()
$1,869
Last-minute flights from Key West to CaribbeanDiscover last-minute flight deals from Key West to Caribbean. Data last updated November 8, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Caribbean. Data last updated November 8, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/1210:59 am -
1 stop6h 22m
Sun 11/156:15 am -
2 stops29h 04m
Deal found 11/4![Multiple Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:04 am -
2 stops13h 55m
Sun 11/2210:54 pm -
1 stop14h 25m
Deal found 11/3![Multiple Airlines logo]()
$366
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1810:04 am -
1 stop22h 50m
Thu 11/2610:16 am -
2 stops26h 03m
Deal found 11/7![Multiple Airlines logo]()
$613
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/2110:04 am -
1 stop23h 21m
Wed 11/259:25 am -
1 stop24h 14m
Deal found 11/5![Multiple Airlines logo]()
$440
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2712:59 pm -
1 stop7h 50m
Mon 12/75:16 pm -
2 stops18h 03m
Deal found 11/8![Multiple Airlines logo]()
$404
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/281:09 pm -
1 stop7h 40m
Mon 12/76:00 am -
2 stops29h 19m
Deal found 11/8![Multiple Airlines logo]()
$444
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/2910:59 am -
1 stop14h 25m
Sun 12/63:03 pm -
2 stops20h 16m
Deal found 11/8![Multiple Airlines logo]()
$549
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/710:59 am -
2 stops13h 08m
Sun 12/138:44 pm -
1 stop14h 35m
Deal found 11/8![Multiple Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/148:00 pm -
1 stop15h 17m
Sat 12/196:44 pm -
2 stops18h 59m
Deal found 11/6![American Airlines logo]()
$533
This Kiwi.com deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/1710:59 am -
1 stop5h 16m
Mon 12/219:25 am -
1 stop25h 56m
Deal found 11/7![Multiple Airlines logo]()
$565
This American Airlines deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2210:15 am -
1 stop6h 58m
Tue 12/297:13 pm -
1 stop15h 32m
Deal found 11/7![American Airlines logo]()
$777
This Kiwi.com deal was found by Cheapflights users on 11/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/235:35 pm -
2 stops29h 39m
Mon 12/284:50 pm -
1 stop18h 29m
Deal found 11/8![Multiple Airlines logo]()
$584
One-way flights from Key West to CaribbeanSearch for one-way flight options from Key West to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 8, 2026.
Search for one-way flight options from Key West to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 8, 2026.
This Breeze Airways deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2612:59 pm -
1 stop24h 51m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Breeze Airways logo]()
$233
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/77:50 pm -
1 stop15h 34m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![American Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/267:22 pm -
2 stops16h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![American Airlines logo]()
$320
This American Airlines deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/128:02 pm -
1 stop14h 56m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![American Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/612:59 pm -
2 stops23h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![United Airlines logo]()
$621
This FlightHub deal was found by Cheapflights users on 11/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/3012:45 pm -
2 stops47h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/7![JetBlue logo]()
$1,308
Find flight deals from Key West to Caribbean
Keep the following information in mind while searching for Key West to Caribbean flight deals. Data was last updated November 8, 2026.
Round-trip from | $366 (Kiwi.com) |
|---|---|
One-way from | $233 (Breeze Airways) |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 8, 2026.
Use the filters below to find and compare flights from Key West to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestSaint Thomas Island
EYW Key West - STT Saint Thomas Island Cyril E King
EYWSTT
Key West
Fri 2/26
12:59 pm-2:50 pm
1 stop24h 51m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$233
Quickest round-trip
Key WestSaint Thomas Island
EYW Key West - STT Saint Thomas Island Cyril E King
EYWSTT
Key West
Sun 2/7
9:58 am-4:14 pm
1 stop5h 16m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$285
Key WestSaint Thomas Island
EYW Key West - STT Saint Thomas Island Cyril E King
EYWSTT
Key West
Fri 2/26
7:22 pm-12:22 pm
2 stops16h 00m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$320
Key WestPunta Cana
EYW Key West - PUJ Punta Cana
EYWPUJ
Key West
Fri 2/12
8:02 pm-11:58 am
1 stop14h 56m
Punta Cana
Wed 12/31
12:00 am-11:30 pm
Nonstop0h 00m
$426
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Sat 11/21
10:04 am-9:25 am
1 stop23h 21m
Nassau Intl
Wed 11/25
9:25 am-9:39 am
1 stop24h 14m
$440
Key WestSaint Thomas Island
EYW Key West - STT Saint Thomas Island Cyril E King
EYWSTT
Key West
Tue 1/26
6:26 pm-1:18 pm
1 stop17h 52m
Saint Thomas Island Cyril E King
Tue 2/2
5:04 pm-1:08 pm
2 stops21h 04m
$498
Key WestSaint Thomas Island
EYW Key West - STT Saint Thomas Island Cyril E King
EYWSTT
Key West
Fri 2/26
12:59 pm-2:50 pm
1 stop24h 51m
Saint Thomas Island Cyril E King
Wed 3/3
3:50 pm-11:26 am
1 stop20h 36m
$516
Key WestSaint Thomas Island
EYW Key West - STT Saint Thomas Island Cyril E King
EYWSTT
Key West
Mon 12/14
8:00 pm-12:17 pm
1 stop15h 17m
Saint Thomas Island Cyril E King
Sat 12/19
6:44 pm-12:43 pm
2 stops18h 59m
$533
Key WestSaint Thomas Island
EYW Key West - STT Saint Thomas Island Cyril E King
EYWSTT
Key West
Fri 2/26
9:55 am-3:58 pm
1 stop5h 03m
Saint Thomas Island Cyril E King
Wed 3/3
6:20 pm-1:37 pm
2 stops20h 17m
$533
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Thu 12/17
10:59 am-4:15 pm
1 stop5h 16m
Nassau Intl
Mon 12/21
9:25 am-11:21 am
1 stop25h 56m
$565
Showing 1-10 of 33 resultsSorted by cheapest first
Best time to book a flight from Key West to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Key West with our price prediction graph.
EYW-STT
EYW-PUJ
EYW-SJU
EYW-NAS
EYW-SDQ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Key West to Caribbean
EYW-0CB
EYW-STT
EYW-PUJ
EYW-SJU
EYW-NAS
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated November 8, 2026.
Read reviews from past customers who have flown American Airlines from Key West to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.4
Overall
7.0
Crew
7.9
Entertainment
6.8
Comfort
7.2
Boarding
7.4
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Food
6.4
Overall
7.0
Crew
7.9
Entertainment
6.8
Comfort
7.2
Boarding
7.4
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Related info for your journey
Find useful and relevant information for your journey from Key West to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Key West to Caribbean
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Complete your trip
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Key West and Caribbean flights
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Top airline flying from Key West to Caribbean
Discover the top airline that operate flights from Key West to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated November 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$421 | Average$616 | FlexibilityNo cancel fee | On-time71% |