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Key West

$138+ Cheap flights from Caribbean to Key West (EYW)

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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — EYW
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap flight deals from Caribbean to Key West

Cheapest flights from Caribbean to Key West
Explore the most affordable flight options available from Caribbean to Key West. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Wed 2/48:05 pm
SJU
-
EYW
1 stop14h 01m
Multiple Airlines
Sun 2/89:46 am
EYW
-
SJU
1 stop12h 47m
Multiple Airlines
Deal found 1/20$289
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Thu 2/54:22 pm
SJU
-
EYW
2 stops17h 47m
Multiple Airlines
Mon 2/91:06 pm
EYW
-
SJU
1 stop19h 41m
Multiple Airlines
Deal found 1/21$308
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/143:53 am
SJU
-
EYW
1 stop6h 13m
Multiple Airlines
Mon 2/162:25 pm
EYW
-
SJU
2 stops23h 41m
Multiple Airlines
Deal found 1/20$343
This Mytrip deal was found by Cheapflights users on 1/21. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/55:50 pm
SJU
-
EYW
2 stops20h 40m
Spirit Airlines
Mon 2/92:25 pm
EYW
-
SJU
3 stops24h 57m
Spirit Airlines
Deal found 1/21$435
This Mytrip deal was found by Cheapflights users on 1/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/48:05 pm
SJU
-
EYW
2 stops16h 51m
Spirit Airlines
Sun 2/812:51 pm
EYW
-
SJU
3 stops29h 07m
Spirit Airlines
Deal found 1/20$485

Find flight deals from Caribbean to Key West

Keep the following information in mind while searching for Caribbean to Key West flight deals. Data was last updated January 21, 2026.

Round-trip from

$272
(Kiwi.com)

One-way from

$138
(Kiwi.com)
From Caribbean to Key West
Search Deals
One-way flight from Caribbean to Key West
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Key West 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 January 21, 2026.
Use the filters below to find and compare flights from Caribbean to Key West that are best for you.

Fly from

Caribbean

Fly to

Key West

Route

Depart

Return

Price

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Wed 2/4

8:05 pm-9:06 am

1 stop14h 01m

Key West

Sun 2/8

9:46 am-11:33 pm

1 stop12h 47m

$289

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Thu 2/5

4:22 pm-9:09 am

2 stops17h 47m

Key West

Mon 2/9

1:06 pm-9:47 am

1 stop19h 41m

$308

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Sat 2/14

3:53 am-9:06 am

1 stop6h 13m

Key West

Mon 2/16

2:25 pm-3:06 pm

2 stops23h 41m

$343

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Thu 2/5

5:50 pm-1:30 pm

2 stops20h 40m

Key West

Mon 2/9

2:25 pm-4:22 pm

3 stops24h 57m

$435

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Wed 2/4

8:05 pm-11:56 am

2 stops16h 51m

Key West

Sun 2/8

12:51 pm-6:58 pm

3 stops29h 07m

$485

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Sat 2/14

3:53 am-9:06 am

1 stop6h 13m

$138

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Sun 2/15

5:20 am-1:30 pm

2 stops33h 10m

$200

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Mon 2/16

7:00 am-4:49 pm

1 stop10h 49m

$243

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Mon 2/16

3:18 pm-11:48 am

3 stops45h 30m

$279

San JuanKey West

SJU - EYW

SJUEYW

San Juan Luis Munoz Marin Intl

Sun 2/15

2:59 am-1:30 pm

2 stops11h 31m

$331

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Best time to book a flight from Caribbean to Key West

Have a flexible travel schedule? Discover the best time to fly to Key West from Caribbean with our price prediction graph.
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 Caribbean to Key West
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 Caribbean to Key West. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Key West from Caribbean?

    Most people fly into Key West (EYW) if they book a flight to Key West from Caribbean. Key West is conveniently located just 2.6 mi from Key West’s city center.

  • Can I find deals for flights from Caribbean to Key West that include hotel bookings?

    Yes. In addition to deals on Caribbean to Key West flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Key West?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Key West.

  • Can I find deals for business class flights from Caribbean to Key West?

    Yes. Cheapflights offers flight deals from Caribbean to Key West by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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