$153+ 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 9/5. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Sep 22 — Sep 291
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Caribbean Islands 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 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 August 23, 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 August 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/412:07 pm -
1 stop14h 08m
Tue 9/85:37 pm -
1 stop15h 47m
Deal found 8/19![Multiple Airlines logo]()
$341
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 8/241:11 pm -
1 stop11h 45m
Thu 8/278:57 pm -
1 stop14h 30m
Deal found 8/19![Multiple Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/19. 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 9/107:40 am -
1 stop6h 13m
Mon 9/141:16 pm -
1 stop6h 44m
Deal found 8/19![Delta logo]()
$501
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/37:53 pm -
1 stop13h 02m
Mon 9/711:00 am -
2 stops25h 34m
Deal found 8/19![Multiple Airlines logo]()
$514
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/1410:59 am -
1 stop5h 16m
Thu 9/1710:20 am -
1 stop21h 48m
Deal found 8/22![Multiple Airlines logo]()
$550
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/510:59 am -
1 stop5h 16m
Mon 10/129:25 am -
1 stop27h 11m
Deal found 8/21![Multiple Airlines logo]()
$607
This American Airlines deal was found by Cheapflights users on 8/22. 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 12/2411:35 am -
1 stop5h 06m
Sun 12/271:04 pm -
1 stop6h 17m
Deal found 8/22![American Airlines logo]()
$613
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/106:27 pm -
2 stops15h 15m
Mon 9/1410:32 am -
1 stop8h 45m
Deal found 8/19![American Airlines logo]()
$657
This Delta deal was found by Cheapflights users on 8/22. 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.
Fri 12/252:56 pm -
1 stop6h 48m
Mon 12/288:10 am -
1 stop12h 48m
Deal found 8/22![Delta logo]()
$729
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/57:10 pm -
1 stop14h 33m
Wed 9/96:00 am -
1 stop13h 17m
Deal found 8/21![American Airlines logo]()
$731
This American Airlines deal was found by Cheapflights users on 8/23. 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 12/2710:15 am -
1 stop6h 26m
Tue 12/297:45 am -
1 stop9h 39m
Deal found 8/23![American Airlines logo]()
$788
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/182:20 pm -
1 stop9h 30m
Tue 9/223:56 pm -
2 stops21h 33m
Deal found 8/18![United Airlines logo]()
$815
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 August 23, 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 August 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/412:07 pm -
1 stop14h 08m
Tue 9/85:37 pm -
1 stop15h 47m
Deal found 8/19![Multiple Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 8/19. 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 9/107:40 am -
1 stop6h 13m
Mon 9/141:16 pm -
1 stop6h 44m
Deal found 8/19![Delta logo]()
$501
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/106:27 pm -
2 stops15h 15m
Mon 9/146:45 pm -
2 stops17h 28m
Deal found 8/19![American Airlines logo]()
$657
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/182:20 pm -
1 stop9h 30m
Tue 9/223:56 pm -
2 stops21h 33m
Deal found 8/18![United Airlines logo]()
$815
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 10/510:59 am -
1 stop5h 16m
Mon 10/124:00 pm -
2 stops41h 24m
Deal found 8/21![Multiple Airlines logo]()
$625
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/57:10 pm -
1 stop14h 33m
Wed 9/96:00 am -
1 stop13h 17m
Deal found 8/21![American Airlines logo]()
$731
This WestJet deal was found by Cheapflights users on 8/22. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:40 am -
2 stops31h 50m
Fri 10/163:30 pm -
2 stops27h 31m
Deal found 8/22![WestJet logo]()
$1,538
This United Airlines deal was found by Cheapflights users on 8/22. 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 12/245:52 pm -
1 stop21h 06m
Mon 12/284:00 pm -
1 stop19h 41m
Deal found 8/22![United Airlines logo]()
$825
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Fri 10/232:15 pm -
1 stop9h 35m
Tue 10/276:35 pm -
1 stop19h 19m
Deal found 8/21![United Airlines logo]()
$872
This Delta deal was found by Cheapflights users on 8/22. 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.
Fri 12/257:15 am -
1 stop5h 45m
Sat 12/262:25 pm -
1 stop6h 33m
Deal found 8/22![Delta logo]()
$1,137
This United Airlines deal was found by Cheapflights users on 8/23. 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 12/284:40 pm -
1 stop19h 09m
Tue 12/294:00 pm -
1 stop19h 41m
Deal found 8/23![United Airlines logo]()
$977
This Delta deal was found by Cheapflights users on 8/22. 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.
Fri 12/252:56 pm -
1 stop6h 48m
Sun 12/272:25 pm -
1 stop6h 33m
Deal found 8/22![Delta logo]()
$1,187
This United Airlines deal was found by Cheapflights users on 8/22. 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 12/245:52 pm -
1 stop21h 06m
Sat 12/261:05 pm -
1 stop23h 02m
Deal found 8/22![United Airlines logo]()
$1,001
This United Airlines deal was found by Cheapflights users on 8/22. 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.
Wed 9/232:20 pm -
1 stop23h 13m
Sat 9/262:35 pm -
1 stop22h 54m
Deal found 8/22![United Airlines logo]()
$1,241
This United Airlines deal was found by Cheapflights users on 8/22. 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 10/12:15 pm -
2 stops25h 23m
Mon 10/512:20 pm -
2 stops25h 09m
Deal found 8/22![United Airlines logo]()
$1,420
This United Airlines deal was found by Cheapflights users on 8/21. 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 12/73:17 pm -
2 stops26h 43m
Fri 12/113:26 pm -
2 stops49h 00m
Deal found 8/21![United Airlines logo]()
$1,902
Last-minute flights from Key West to Caribbean IslandsDiscover last-minute flight deals from Key West to Caribbean Islands. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Caribbean Islands. Data last updated August 23, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 8/241:11 pm -
1 stop11h 45m
Thu 8/278:57 pm -
1 stop14h 30m
Deal found 8/19![Multiple Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/37:53 pm -
1 stop13h 02m
Mon 9/711:00 am -
2 stops25h 34m
Deal found 8/19![Multiple Airlines logo]()
$514
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/37:53 pm -
1 stop13h 02m
Mon 9/79:55 am -
1 stop26h 39m
Deal found 8/19![Breeze Airways logo]()
$823
This Kiwi.com deal was found by Cheapflights users on 8/19. 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 9/412:07 pm -
1 stop14h 08m
Tue 9/85:37 pm -
1 stop15h 47m
Deal found 8/19![Multiple Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/57:10 pm -
1 stop14h 33m
Wed 9/94:38 pm -
2 stops20h 33m
Deal found 8/21![American Airlines logo]()
$731
This Delta deal was found by Cheapflights users on 8/19. 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 9/107:40 am -
1 stop6h 13m
Mon 9/141:16 pm -
1 stop6h 44m
Deal found 8/19![Delta logo]()
$501
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/106:27 pm -
2 stops15h 15m
Mon 9/1410:32 am -
1 stop8h 45m
Deal found 8/19![American Airlines logo]()
$657
This Kiwi.com deal was found by Cheapflights users on 8/22. 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 9/1410:59 am -
1 stop5h 16m
Thu 9/1710:20 am -
1 stop21h 48m
Deal found 8/22![Multiple Airlines logo]()
$550
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 9/182:20 pm -
1 stop9h 30m
Tue 9/223:56 pm -
2 stops21h 33m
Deal found 8/18![United Airlines logo]()
$815
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Wed 9/232:20 pm -
1 stop23h 13m
Sat 9/262:35 pm -
1 stop22h 54m
Deal found 8/18![United Airlines logo]()
$1,241
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 August 23, 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 August 23, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/53:48 pm -
1 stop9h 08m
Deal found 8/20![Multiple Airlines logo]()
$153
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/611:04 am -
1 stop13h 30m
Deal found 8/20![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/412:07 pm -
1 stop14h 08m
Deal found 8/20![Multiple Airlines logo]()
$171
This Breeze Airways deal was found by Cheapflights users on 8/20. 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.
Sun 1/1712:06 pm -
1 stop20h 24m
Deal found 8/20![Breeze Airways logo]()
$201
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 9/2512:59 pm -
2 stops30h 16m
Deal found 8/20![Multiple Airlines logo]()
$205
This American Airlines deal was found by Cheapflights users on 8/20. 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 11/1510:18 am -
1 stop12h 08m
Deal found 8/20![American Airlines logo]()
$387
This American Airlines deal was found by Cheapflights users on 8/20. 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 1/28:03 pm -
1 stop13h 48m
Deal found 8/20![American Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/52:25 pm -
2 stops19h 18m
Deal found 8/20![American Airlines logo]()
$398
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 1/28:59 am -
2 stops16h 08m
Deal found 8/20![Multiple Airlines logo]()
$567
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 11/1512:01 pm -
2 stops7h 34m
Deal found 8/20![Multiple Airlines logo]()
$654
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Sun 1/176:20 pm -
2 stops21h 02m
Deal found 8/20![United Airlines logo]()
$1,666
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 August 23, 2026.
Round-trip from | $341 (Kiwi.com) |
|---|---|
One-way from | $153 (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 7,457,451 searches. Data last updated August 23, 2026.
Use the filters below to find and compare flights from Key West to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Fri 9/4
12:07 pm-2:15 am
1 stop14h 08m
San Juan Luis Munoz Marin Intl
Tue 9/8
5:37 pm-9:24 am
1 stop15h 47m
$341
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Thu 9/10
7:40 am-1:53 pm
1 stop6h 13m
Nassau Intl
Mon 9/14
1:16 pm-8:00 pm
1 stop6h 44m
$501
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Mon 10/5
10:59 am-4:15 pm
1 stop5h 16m
Nassau Intl
Mon 10/12
4:00 pm-9:24 am
2 stops41h 24m
$625
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Thu 9/10
6:27 pm-9:42 am
2 stops15h 15m
Nassau Intl
Mon 9/14
6:45 pm-12:13 pm
2 stops17h 28m
$657
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Sat 9/5
7:10 pm-9:43 am
1 stop14h 33m
San Juan Luis Munoz Marin Intl
Wed 9/9
6:00 am-7:17 pm
1 stop13h 17m
$731
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Fri 9/18
2:20 pm-11:50 pm
1 stop9h 30m
San Juan Luis Munoz Marin Intl
Tue 9/22
3:56 pm-1:29 pm
2 stops21h 33m
$815
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Thu 12/24
5:52 pm-2:58 pm
1 stop21h 06m
Nassau Intl
Mon 12/28
4:00 pm-11:41 am
1 stop19h 41m
$825
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Fri 10/23
2:15 pm-11:50 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Tue 10/27
6:35 pm-1:54 pm
1 stop19h 19m
$872
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Mon 12/28
4:40 pm-11:49 am
1 stop19h 09m
Nassau Intl
Tue 12/29
4:00 pm-11:41 am
1 stop19h 41m
$977
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Thu 12/24
5:52 pm-2:58 pm
1 stop21h 06m
Nassau Intl
Sat 12/26
1:05 pm-12:07 pm
1 stop23h 02m
$1,001
Showing 1-10 of 25 resultsSorted by cheapest first
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.
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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
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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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Key West to Caribbean Islands by cabin class
Find flights from Key West to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Key West and Caribbean Islands flights
Browse other Key West and Caribbean Islands flight options. Last updated on August 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 7,457,451 searches. Data last updated August 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$415 | Average$586 | FlexibilityNo cancel fee | On-time71% |