$166+ Cheap flights from Key West (EYW) to Caribbean Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
3月 17 — 3月 241
1 adult, Economy
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Cheapest flights from Key West to Caribbean IslandsExplore the most affordable flight options available from Key West to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 2月 15, 2026.
Explore the most affordable flight options available from Key West to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 2月 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
月 3/29:49 am
EYW
- SJU
1 stop15h 36m
Multiple Airlines
金 3/610:12 pm
SJU
- EYW
2 stops34h 54m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
金 2/271:06 pm
EYW
- SJU
1 stop10h 37m
Multiple Airlines
火 3/37:00 am
SJU
- EYW
1 stop6h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
木 5/1412:06 pm
EYW
- SJU
1 stop24h 27m
Multiple Airlines
日 5/179:54 pm
SJU
- EYW
1 stop13h 17m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$307
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
日 3/12:25 pm
EYW
- SJU
1 stop24h 06m
Multiple Airlines
水 3/45:25 pm
SJU
- EYW
1 stop16h 41m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$311
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
月 4/132:35 pm
EYW
- SJU
1 stop21h 14m
Spirit Airlines
木 4/169:54 pm
SJU
- EYW
1 stop13h 17m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
水 5/1311:46 am
EYW
- SJU
2 stops24h 47m
Multiple Airlines
日 5/179:54 pm
SJU
- EYW
1 stop13h 17m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
木 5/1412:06 pm
EYW
- SJU
1 stop8h 43m
Multiple Airlines
月 5/189:54 pm
SJU
- EYW
2 stops37h 12m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
土 2/2111:53 am
EYW
- SJU
2 stops21h 54m
Multiple Airlines
水 2/257:00 am
SJU
- EYW
1 stop28h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
木 2/2611:01 am
EYW
- SJU
1 stop14h 24m
Multiple Airlines
土 2/282:59 am
SJU
- EYW
2 stops35h 31m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 2/15. 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.
日 7/1911:28 am
EYW
- NAS
1 stop8h 17m
American Airlines
木 7/2310:19 am
NAS
- EYW
1 stop9h 02m
American Airlines
Deal found 2/15![American Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
月 3/302:35 pm
EYW
- NAS
1 stop4h 40m
Multiple Airlines
月 4/64:00 pm
NAS
- EYW
1 stop19h 30m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$485
This Mytrip deal was found by Cheapflights users on 2/13. 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.
日 3/1512:25 pm
EYW
- NAS
1 stop6h 50m
Multiple Airlines
日 3/227:15 am
NAS
- EYW
1 stop4h 15m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$491
Best flights from Key West to Caribbean IslandsDiscover carefully curated flight deals from Key West to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 2月 15, 2026.
Discover carefully curated flight deals from Key West to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 2月 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
月 3/29:49 am
EYW
- SJU
1 stop15h 36m
Multiple Airlines
金 3/610:12 pm
SJU
- EYW
2 stops34h 54m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$297
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
月 4/132:35 pm
EYW
- SJU
1 stop21h 14m
Spirit Airlines
木 4/169:54 pm
SJU
- EYW
1 stop13h 17m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 2/15. 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.
日 7/1911:28 am
EYW
- NAS
1 stop8h 17m
American Airlines
木 7/2310:19 am
NAS
- EYW
1 stop9h 02m
American Airlines
Deal found 2/15![American Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
水 5/1311:46 am
EYW
- SJU
2 stops24h 47m
Multiple Airlines
日 5/179:54 pm
SJU
- EYW
1 stop13h 17m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
木 5/1412:06 pm
EYW
- SJU
1 stop8h 43m
Multiple Airlines
日 5/179:54 pm
SJU
- EYW
2 stops14h 37m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
水 5/1311:46 am
EYW
- SJU
2 stops24h 47m
Multiple Airlines
火 5/192:09 pm
SJU
- EYW
1 stop20h 57m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
木 2/2611:01 am
EYW
- SJU
1 stop14h 24m
Multiple Airlines
土 2/282:59 am
SJU
- EYW
2 stops35h 31m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$352
This American Airlines deal was found by Cheapflights users on 2/11. 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.
金 4/2411:24 am
EYW
- NAS
1 stop3h 22m
American Airlines
水 4/2910:19 am
NAS
- EYW
1 stop12h 39m
American Airlines
Deal found 2/11![American Airlines logo]()
$531
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
水 5/2011:46 am
EYW
- SJU
2 stops12h 43m
Multiple Airlines
水 5/273:36 pm
SJU
- EYW
1 stop19h 35m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
水 7/2912:26 pm
EYW
- SJU
1 stop8h 15m
Multiple Airlines
火 8/46:10 am
SJU
- EYW
1 stop28h 56m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
金 5/1512:06 pm
EYW
- SJU
1 stop8h 43m
Multiple Airlines
月 5/189:54 pm
SJU
- EYW
2 stops37h 12m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 2/11. 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.
木 8/67:09 pm
EYW
- MHH
1 stop16h 05m
American Airlines
土 8/811:50 am
MHH
- EYW
1 stop6h 49m
American Airlines
Deal found 2/11![American Airlines logo]()
$632
This American Airlines deal was found by Cheapflights users on 2/11. 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.
木 4/306:45 am
EYW
- MHH
1 stop6h 35m
American Airlines
土 5/21:00 pm
MHH
- EYW
1 stop9h 58m
American Airlines
Deal found 2/11![American Airlines logo]()
$635
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
月 3/302:35 pm
EYW
- NAS
1 stop4h 40m
Multiple Airlines
月 4/64:00 pm
NAS
- EYW
1 stop19h 30m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$485
This American Airlines deal was found by Cheapflights users on 2/11. 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.
日 3/297:42 pm
EYW
- FPO
1 stop18h 45m
American Airlines
日 4/512:17 pm
FPO
- EYW
1 stop6h 55m
American Airlines
Deal found 2/11![American Airlines logo]()
$738
This Mytrip deal was found by Cheapflights users on 2/13. 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.
日 3/1512:25 pm
EYW
- NAS
1 stop6h 50m
Multiple Airlines
日 3/227:15 am
NAS
- EYW
1 stop4h 15m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$491
This American Airlines deal was found by Cheapflights users on 2/12. 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.
月 5/186:45 am
EYW
- EIS
1 stop4h 33m
American Airlines
水 5/278:19 am
EIS
- EYW
1 stop10h 51m
American Airlines
Deal found 2/12![American Airlines logo]()
$749
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
金 4/2412:06 pm
EYW
- NAS
1 stop26h 39m
Multiple Airlines
水 4/2911:30 am
NAS
- EYW
1 stop23h 41m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$494
This American Airlines deal was found by Cheapflights users on 2/14. 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.
月 5/1111:24 am
EYW
- EIS
1 stop9h 46m
American Airlines
火 5/191:47 pm
EIS
- EYW
1 stop9h 11m
American Airlines
Deal found 2/14![American Airlines logo]()
$749
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
日 3/2912:25 pm
EYW
- NAS
1 stop6h 50m
Multiple Airlines
日 4/54:00 pm
NAS
- EYW
2 stops17h 09m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 2/15. 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.
水 4/17:42 pm
EYW
- MHH
1 stop19h 48m
American Airlines
水 4/81:00 pm
MHH
- EYW
1 stop9h 58m
American Airlines
Deal found 2/15![American Airlines logo]()
$1,088
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
日 3/2912:25 pm
EYW
- FPO
1 stop23h 25m
Multiple Airlines
日 4/510:45 am
FPO
- EYW
2 stops23h 26m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$712
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
水 4/112:25 pm
EYW
- MHH
2 stops19h 10m
Multiple Airlines
水 4/84:50 pm
MHH
- EYW
1 stop18h 40m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$749
This United Airlines deal was found by Cheapflights users on 2/13. 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.
日 5/313:50 pm
EYW
- KIN
2 stops47h 04m
United Airlines
水 6/32:59 pm
KIN
- EYW
2 stops47h 08m
United Airlines
Deal found 2/13![United Airlines logo]()
$5,383
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
木 4/3012:06 pm
EYW
- MHH
1 stop4h 10m
Multiple Airlines
土 5/21:30 pm
MHH
- EYW
2 stops26h 12m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$855
Last-minute flights from Key West to Caribbean IslandsDiscover last-minute flight deals from Key West to Caribbean Islands. Data last updated 2月 15, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Caribbean Islands. Data last updated 2月 15, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 2/11. 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.
土 2/2111:53 am
EYW
- SJU
2 stops21h 54m
Multiple Airlines
水 2/257:00 am
SJU
- EYW
1 stop28h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 2/14. 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.
火 2/241:01 pm
EYW
- SJU
1 stop24h 24m
Multiple Airlines
木 2/263:53 am
SJU
- EYW
1 stop9h 33m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$408
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
木 2/2611:01 am
EYW
- SJU
1 stop14h 24m
Multiple Airlines
土 2/282:59 am
SJU
- EYW
2 stops35h 31m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$352
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
金 2/271:06 pm
EYW
- SJU
1 stop10h 37m
Multiple Airlines
火 3/37:00 am
SJU
- EYW
1 stop6h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
日 3/12:25 pm
EYW
- SJU
1 stop24h 06m
Multiple Airlines
水 3/45:25 pm
SJU
- EYW
1 stop16h 41m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$311
This Mytrip deal was found by Cheapflights users on 2/15. 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.
日 3/12:25 pm
EYW
- SJU
2 stops18h 52m
Spirit Airlines
水 3/46:27 pm
SJU
- EYW
2 stops20h 03m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$406
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
月 3/29:49 am
EYW
- SJU
1 stop15h 36m
Multiple Airlines
金 3/610:12 pm
SJU
- EYW
2 stops34h 54m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$297
This Mytrip deal was found by Cheapflights users on 2/13. 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.
日 3/1512:25 pm
EYW
- NAS
1 stop6h 50m
Multiple Airlines
日 3/227:15 am
NAS
- EYW
1 stop4h 15m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$491
This Mytrip deal was found by Cheapflights users on 2/14. 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.
火 3/2412:25 pm
EYW
- SJU
1 stop6h 30m
Spirit Airlines
月 3/308:47 pm
SJU
- EYW
2 stops14h 43m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$390
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
日 3/2912:25 pm
EYW
- NAS
1 stop6h 50m
Multiple Airlines
日 4/54:00 pm
NAS
- EYW
2 stops17h 09m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 2/12. 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.
日 3/297:42 pm
EYW
- NAS
1 stop19h 01m
American Airlines
日 4/510:14 am
NAS
- EYW
1 stop8h 58m
American Airlines
Deal found 2/12![American Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 2/13. 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.
月 3/302:35 pm
EYW
- NAS
1 stop4h 40m
Multiple Airlines
月 4/64:00 pm
NAS
- EYW
1 stop19h 30m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$485
One-way flights from Key West to Caribbean IslandsSearch for one-way flight options from Key West to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated 2月 15, 2026.
Search for one-way flight options from Key West to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated 2月 15, 2026.
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
金 3/69:49 am
EYW
- SJU
1 stop27h 36m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$166
This Mytrip deal was found by Cheapflights users on 2/12. 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.
日 3/2912:25 pm
EYW
- NAS
1 stop6h 50m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$178
This Mytrip deal was found by Cheapflights users on 2/11. 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.
日 2/222:25 pm
EYW
- SJU
2 stops18h 52m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 2/12. 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.
土 2/217:36 pm
EYW
- SJU
1 stop13h 24m
American Airlines
Deal found 2/12![American Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
土 2/2111:53 am
EYW
- SJU
3 stops26h 38m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 2/11. 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.
日 2/222:46 pm
EYW
- SJU
1 stop8h 12m
Delta
Deal found 2/11![Delta logo]()
$358
This United Airlines deal was found by Cheapflights users on 2/14. 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.
土 2/214:34 pm
EYW
- SJU
1 stop12h 37m
United Airlines
Deal found 2/14![United Airlines logo]()
$518
Find flight deals from Key West to Caribbean Islands
Keep the following information in mind while searching for Key West to Caribbean Islands flight deals. Data was last updated 2月 15, 2026.
Round-trip from | $297 (Kiwi.com) |
|---|---|
One-way from | $166 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West to Caribbean Islands 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 2,558,603 searches. Data last updated 2月 15, 2026.
Use the filters below to find and compare flights from Key West to Caribbean Islands that are best for you.
Fly from
Key West
Fly to
Caribbean Islands
Route
Depart
Return
Price
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
月 3/2
9:49 am-2:25 am
1 stop15h 36m
San Juan Luis Munoz Marin Intl
金 3/6
10:12 pm-8:06 am
2 stops34h 54m
$297
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
月 4/13
2:35 pm-11:49 am
1 stop21h 14m
San Juan Luis Munoz Marin Intl
木 4/16
9:54 pm-11:11 am
1 stop13h 17m
$321
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
水 5/13
11:46 am-12:33 pm
2 stops24h 47m
San Juan Luis Munoz Marin Intl
日 5/17
9:54 pm-11:11 am
1 stop13h 17m
$330
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
木 5/14
12:06 pm-8:49 pm
1 stop8h 43m
San Juan Luis Munoz Marin Intl
日 5/17
9:54 pm-12:31 pm
2 stops14h 37m
$346
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
水 5/13
11:46 am-12:33 pm
2 stops24h 47m
San Juan Luis Munoz Marin Intl
火 5/19
2:09 pm-11:06 am
1 stop20h 57m
$347
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
木 2/26
11:01 am-2:25 am
1 stop14h 24m
San Juan Luis Munoz Marin Intl
土 2/28
2:59 am-1:30 pm
2 stops35h 31m
$352
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
水 5/20
11:46 am-12:29 am
2 stops12h 43m
San Juan Luis Munoz Marin Intl
水 5/27
3:36 pm-11:11 am
1 stop19h 35m
$373
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
水 7/29
12:26 pm-8:41 pm
1 stop8h 15m
San Juan Luis Munoz Marin Intl
火 8/4
6:10 am-11:06 am
1 stop28h 56m
$377
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
金 5/15
12:06 pm-8:49 pm
1 stop8h 43m
San Juan Luis Munoz Marin Intl
月 5/18
9:54 pm-11:06 am
2 stops37h 12m
$379
Key WestNassau
EYW - NAS
EYWNAS
Key West
日 7/19
11:28 am-7:45 pm
1 stop8h 17m
Nassau Intl
木 7/23
10:19 am-7:21 pm
1 stop9h 02m
$478
Showing 1-10 of 32 results
Best time to book a flight from Key West to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Key West with our price prediction graph.
EYW-SJU
EYW-NAS
EYW-MHH
EYW-FPO
EYW-EIS
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 Islands
EYW-zzEPX
EYW-SJU
EYW-NAS
EYW-MHH
EYW-FPO
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Key West to Caribbean Islands. 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 Islands
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Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
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Key West and Caribbean Islands flights
Browse other Key West and Caribbean Islands flight options. Last updated on 2月 15, 2026.
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Key West to Caribbean Islands flights
Consider these flights traveling from Key West to Caribbean Islands.
Top airline flying from Key West to Caribbean Islands
Discover the top airline that operate flights from Key West to Caribbean Islands. 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 2,558,603 searches. Data last updated 2月 15, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$376 | Average$495 | FlexibilityNo cancel fee | On-time71% |