$163+ 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 7/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Jun 11 — Jun 181
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Key West to Caribbean Islands
Cheapest
Best
Last-minute
One-way
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 May 12, 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 May 12, 2026.
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 9/21:49 pm
EYW
- SJU
1 stop7h 25m
American Airlines
Sun 9/610:33 am
SJU
- EYW
1 stop9h 06m
American Airlines
Deal found 5/12![American Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/119:16 pm
EYW
- SJU
2 stops30h 41m
Multiple Airlines
Mon 6/155:15 pm
SJU
- EYW
1 stop19h 19m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 5/10. 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 7/711:28 am
EYW
- NAS
1 stop6h 26m
American Airlines
Thu 7/91:31 pm
NAS
- EYW
1 stop5h 35m
American Airlines
Deal found 5/10![American Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Thu 6/2510:56 am
EYW
- NAS
2 stops26h 54m
Multiple Airlines
Thu 7/29:55 am
NAS
- EYW
1 stop9h 18m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Tue 5/261:14 pm
EYW
- SJU
1 stop10h 45m
Multiple Airlines
Sat 5/309:45 pm
SJU
- EYW
2 stops36h 42m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$558
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 6/1912:07 pm
EYW
- NAS
1 stop4h 18m
Multiple Airlines
Sun 6/214:25 pm
NAS
- EYW
1 stop19h 02m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/1812:05 pm
EYW
- NAS
1 stop4h 20m
Multiple Airlines
Sun 6/214:25 pm
NAS
- EYW
1 stop19h 02m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 5/2711:46 am
EYW
- SJU
2 stops28h 04m
Multiple Airlines
Sat 5/303:03 am
SJU
- EYW
1 stop8h 22m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$582
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/712:05 pm
EYW
- SJU
1 stop14h 03m
Multiple Airlines
Sun 6/145:15 pm
SJU
- EYW
1 stop19h 16m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$593
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Fri 6/2611:28 am
EYW
- NAS
1 stop8h 28m
American Airlines
Fri 7/33:02 pm
NAS
- EYW
1 stop19h 56m
American Airlines
Deal found 5/12![American Airlines logo]()
$601
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 7/91:47 pm
EYW
- NAS
1 stop5h 56m
American Airlines
Mon 7/131:56 pm
NAS
- EYW
1 stop5h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$606
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Fri 6/51:39 pm
EYW
- NAS
1 stop6h 17m
American Airlines
Tue 6/98:00 am
NAS
- EYW
1 stop11h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$631
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 May 12, 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 May 12, 2026.
This American Airlines deal was found by Cheapflights users on 5/8. 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.
Wed 9/210:16 am
EYW
- SJU
1 stop8h 08m
American Airlines
Sun 9/66:00 am
SJU
- EYW
1 stop4h 56m
American Airlines
Deal found 5/8![American Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/119:16 pm
EYW
- SJU
2 stops30h 41m
Multiple Airlines
Mon 6/155:15 pm
SJU
- EYW
1 stop19h 19m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$474
This American Airlines deal was found by Cheapflights users on 5/9. 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 7/71:47 pm
EYW
- NAS
1 stop5h 56m
American Airlines
Thu 7/91:31 pm
NAS
- EYW
1 stop5h 35m
American Airlines
Deal found 5/9![American Airlines logo]()
$536
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Thu 6/2510:56 am
EYW
- NAS
2 stops26h 54m
Multiple Airlines
Thu 7/29:55 am
NAS
- EYW
1 stop9h 18m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/1812:05 pm
EYW
- NAS
1 stop4h 20m
Multiple Airlines
Sun 6/214:25 pm
NAS
- EYW
1 stop19h 02m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$573
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 6/67:49 pm
EYW
- NAS
1 stop13h 38m
American Airlines
Tue 6/98:00 am
NAS
- EYW
1 stop11h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$606
This United Airlines deal was found by Cheapflights users on 5/9. 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 7/132:26 pm
EYW
- KIN
2 stops24h 28m
United Airlines
Wed 7/152:56 pm
KIN
- EYW
2 stops21h 34m
United Airlines
Deal found 5/9![United Airlines logo]()
$1,337
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/712:05 pm
EYW
- SJU
2 stops35h 54m
Multiple Airlines
Sun 6/145:15 pm
SJU
- EYW
1 stop19h 16m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$580
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Fri 6/51:39 pm
EYW
- NAS
1 stop6h 17m
American Airlines
Tue 6/98:00 am
NAS
- EYW
1 stop11h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$631
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 5/2711:46 am
EYW
- SJU
2 stops28h 04m
Multiple Airlines
Sat 5/303:03 am
SJU
- EYW
1 stop8h 22m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$582
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/411:28 am
EYW
- NAS
1 stop8h 02m
American Airlines
Tue 6/92:55 pm
NAS
- EYW
1 stop4h 15m
American Airlines
Deal found 5/12![American Airlines logo]()
$631
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 6/2612:07 pm
EYW
- NAS
1 stop4h 18m
Multiple Airlines
Fri 7/34:00 pm
NAS
- EYW
2 stops42h 05m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$632
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 6/512:07 pm
EYW
- NAS
1 stop4h 18m
Multiple Airlines
Tue 6/94:00 pm
NAS
- EYW
2 stops42h 06m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$646
This American Airlines deal was found by Cheapflights users on 5/10. 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 11/612:00 pm
EYW
- FPO
1 stop23h 43m
American Airlines
Mon 11/912:23 pm
FPO
- EYW
1 stop7h 06m
American Airlines
Deal found 5/10![American Airlines logo]()
$742
This Kiwi.com deal was found by Cheapflights users on 5/9. 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.
Tue 7/71:14 pm
EYW
- NAS
2 stops6h 01m
Multiple Airlines
Thu 7/99:55 am
NAS
- EYW
1 stop9h 18m
Multiple Airlines
Deal found 5/9![Multiple Airlines logo]()
$660
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Thu 6/1111:28 am
EYW
- MHH
1 stop3h 31m
American Airlines
Wed 6/1712:51 pm
MHH
- EYW
1 stop6h 19m
American Airlines
Deal found 5/12![American Airlines logo]()
$762
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Thu 6/412:05 pm
EYW
- NAS
1 stop4h 20m
Multiple Airlines
Tue 6/94:00 pm
NAS
- EYW
2 stops42h 06m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$669
Last-minute flights from Key West to Caribbean IslandsDiscover last-minute flight deals from Key West to Caribbean Islands. Data last updated May 12, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Caribbean Islands. Data last updated May 12, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 5/10. 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.
Tue 5/261:14 pm
EYW
- SJU
1 stop10h 45m
Multiple Airlines
Sat 5/309:45 pm
SJU
- EYW
2 stops36h 42m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$558
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 5/2711:46 am
EYW
- SJU
2 stops28h 04m
Multiple Airlines
Sat 5/303:03 am
SJU
- EYW
1 stop8h 22m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$582
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Fri 6/51:39 pm
EYW
- NAS
1 stop6h 17m
American Airlines
Tue 6/98:00 am
NAS
- EYW
1 stop11h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$631
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 6/512:07 pm
EYW
- NAS
1 stop4h 18m
Multiple Airlines
Tue 6/94:00 pm
NAS
- EYW
2 stops42h 06m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$645
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Sat 6/67:49 pm
EYW
- NAS
1 stop13h 38m
American Airlines
Tue 6/98:00 am
NAS
- EYW
1 stop11h 10m
American Airlines
Deal found 5/12![American Airlines logo]()
$606
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/712:05 pm
EYW
- SJU
1 stop14h 03m
Multiple Airlines
Sun 6/145:15 pm
SJU
- EYW
1 stop19h 16m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$593
This Kiwi.com deal was found by Cheapflights users on 5/8. 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 6/119:16 pm
EYW
- SJU
2 stops30h 41m
Multiple Airlines
Mon 6/155:15 pm
SJU
- EYW
1 stop19h 19m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$474
This Kiwi.com deal was found by Cheapflights users on 5/10. 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 6/1812:05 pm
EYW
- NAS
1 stop4h 20m
Multiple Airlines
Sun 6/214:25 pm
NAS
- EYW
1 stop19h 02m
Multiple Airlines
Deal found 5/10![Multiple Airlines logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 6/1912:07 pm
EYW
- NAS
1 stop4h 18m
Multiple Airlines
Sun 6/214:25 pm
NAS
- EYW
1 stop19h 02m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$566
This Kiwi.com deal was found by Cheapflights users on 5/11. 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.
Thu 6/2510:56 am
EYW
- NAS
2 stops26h 54m
Multiple Airlines
Thu 7/29:55 am
NAS
- EYW
1 stop9h 18m
Multiple Airlines
Deal found 5/11![Multiple Airlines logo]()
$537
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Fri 6/2611:28 am
EYW
- NAS
1 stop8h 28m
American Airlines
Fri 7/33:02 pm
NAS
- EYW
1 stop19h 56m
American Airlines
Deal found 5/12![American Airlines logo]()
$601
This Kiwi.com deal was found by Cheapflights users on 5/12. 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.
Fri 6/2612:07 pm
EYW
- NAS
1 stop4h 18m
Multiple Airlines
Fri 7/34:00 pm
NAS
- EYW
2 stops42h 05m
Multiple Airlines
Deal found 5/12![Multiple Airlines logo]()
$632
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 May 12, 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 May 12, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/8. 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.
Tue 7/211:14 pm
EYW
- SJU
1 stop11h 27m
Multiple Airlines
Deal found 5/8![Multiple Airlines logo]()
$163
This American Airlines deal was found by Cheapflights users on 5/8. 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.
Tue 7/217:33 pm
EYW
- SJU
2 stops15h 31m
American Airlines
Deal found 5/8![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 5/10. 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 7/207:40 pm
EYW
- SJU
1 stop14h 05m
American Airlines
Deal found 5/10![American Airlines logo]()
$513
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 May 12, 2026.
Round-trip from | $441 (American Airlines) |
|---|---|
One-way from | $163 (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 May 12, 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 - SJU
EYWSJU
Key West
Wed 9/2
10:16 am-6:24 pm
1 stop8h 08m
San Juan Luis Munoz Marin Intl
Sun 9/6
6:00 am-10:56 am
1 stop4h 56m
$441
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Thu 6/11
9:16 pm-3:57 am
2 stops30h 41m
San Juan Luis Munoz Marin Intl
Mon 6/15
5:15 pm-12:34 pm
1 stop19h 19m
$474
Key WestNassau
EYW - NAS
EYWNAS
Key West
Tue 7/7
1:47 pm-7:43 pm
1 stop5h 56m
Nassau Intl
Thu 7/9
1:31 pm-7:06 pm
1 stop5h 35m
$536
Key WestNassau
EYW - NAS
EYWNAS
Key West
Thu 6/25
10:56 am-1:50 pm
2 stops26h 54m
Nassau Intl
Thu 7/2
9:55 am-7:13 pm
1 stop9h 18m
$537
Key WestNassau
EYW - NAS
EYWNAS
Key West
Thu 6/18
12:05 pm-4:25 pm
1 stop4h 20m
Nassau Intl
Sun 6/21
4:25 pm-11:27 am
1 stop19h 02m
$573
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Sun 6/7
12:05 pm-11:59 pm
2 stops35h 54m
San Juan Luis Munoz Marin Intl
Sun 6/14
5:15 pm-12:31 pm
1 stop19h 16m
$580
Key WestSan Juan
EYW - SJU
EYWSJU
Key West
Wed 5/27
11:46 am-3:50 pm
2 stops28h 04m
San Juan Luis Munoz Marin Intl
Sat 5/30
3:03 am-11:25 am
1 stop8h 22m
$582
Key WestNassau
EYW - NAS
EYWNAS
Key West
Sat 6/6
7:49 pm-9:27 am
1 stop13h 38m
Nassau Intl
Tue 6/9
8:00 am-7:10 pm
1 stop11h 10m
$606
Key WestNassau
EYW - NAS
EYWNAS
Key West
Fri 6/5
1:39 pm-7:56 pm
1 stop6h 17m
Nassau Intl
Tue 6/9
8:00 am-7:10 pm
1 stop11h 10m
$631
Key WestNassau
EYW - NAS
EYWNAS
Key West
Thu 6/4
11:28 am-7:30 pm
1 stop8h 02m
Nassau Intl
Tue 6/9
2:55 pm-7:10 pm
1 stop4h 15m
$631
Showing 1-10 of 20 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.
EYW-SJU
EYW-NAS
EYW-KIN
EYW-FPO
EYW-MHH
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-KIN
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 May 12, 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 2,558,603 searches. Data last updated May 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$390 | Average$495 | FlexibilityNo cancel fee | On-time71% |