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Caribbean Islands

$272+ Cheap flights from Key West (EYW) to Caribbean Islands

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Aug 3 — Aug 101
Mon 8/3
Mon 8/10
1 adult, Economy
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Cheap flight deals from Key West to Caribbean Islands

Cheapest flights from Key West to Caribbean Islands
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 July 4, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/211:11 pm
EYW
-
SJU
1 stop11h 45m
Multiple Airlines
Sun 8/236:35 am
SJU
-
EYW
2 stops29h 56m
Multiple Airlines
Deal found 7/3$272
This American Airlines deal was found by Cheapflights users on 7/1. 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 9/24:50 pm
EYW
-
SJU
1 stop7h 09m
American Airlines
Sun 9/66:00 am
SJU
-
EYW
1 stop4h 56m
American Airlines
Deal found 7/1$451
This American Airlines deal was found by Cheapflights users on 7/1. 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 12/412:00 pm
EYW
-
SJU
1 stop4h 52m
American Airlines
Sat 12/122:50 pm
SJU
-
EYW
1 stop5h 44m
American Airlines
Deal found 7/1$481
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 8/1712:07 pm
EYW
-
NAS
1 stop5h 03m
Multiple Airlines
Sun 8/239:55 am
NAS
-
EYW
1 stop9h 18m
Multiple Airlines
Deal found 6/30$534
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/111:30 am
EYW
-
MHH
1 stop25h 47m
American Airlines
Sun 9/61:30 pm
MHH
-
EYW
1 stop6h 09m
American Airlines
Deal found 7/3$568
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/137:40 pm
EYW
-
MHH
1 stop13h 53m
American Airlines
Fri 7/1710:13 am
MHH
-
EYW
1 stop8h 53m
American Airlines
Deal found 6/29$611
This American Airlines deal was found by Cheapflights users on 7/1. 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 8/157:10 pm
EYW
-
NAS
1 stop22h 29m
American Airlines
Sat 8/222:36 pm
NAS
-
EYW
1 stop4h 04m
American Airlines
Deal found 7/1$623
This American Airlines deal was found by Cheapflights users on 6/29. 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 7/2911:28 am
EYW
-
MHH
1 stop3h 44m
American Airlines
Wed 8/511:52 am
MHH
-
EYW
1 stop7h 47m
American Airlines
Deal found 6/29$627
This American Airlines deal was found by Cheapflights users on 6/29. 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 22m
American Airlines
Mon 7/131:56 pm
NAS
-
EYW
1 stop5h 10m
American Airlines
Deal found 6/29$764
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1710:15 am
EYW
-
EIS
1 stop6h 10m
American Airlines
Mon 8/2412:36 pm
EIS
-
EYW
1 stop7h 03m
American Airlines
Deal found 7/3$802
This American Airlines deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1611:28 am
EYW
-
NAS
1 stop3h 45m
American Airlines
Fri 7/176:45 pm
NAS
-
EYW
1 stop18h 23m
American Airlines
Deal found 7/3$854
This Expedia deal was found by Cheapflights users on 7/1. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/412:45 pm
EYW
-
SJU
2 stops14h 03m
JetBlue
Sat 12/124:40 pm
SJU
-
EYW
2 stops20h 13m
JetBlue
Deal found 7/1$855

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 July 4, 2026.

Round-trip from

$272
(Kiwi.com)
From Key West to Caribbean Islands
Search Deals

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 July 4, 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

Price

Cheapest round-trip

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 9/2

1:50 pm-11:59 pm

1 stop10h 09m

San Juan Luis Munoz Marin Intl

Sun 9/6

7:24 pm-12:55 pm

2 stops17h 31m

$451
Quickest round-trip

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 12/4

12:00 pm-5:52 pm

1 stop4h 52m

San Juan Luis Munoz Marin Intl

Sat 12/12

2:50 pm-7:34 pm

1 stop5h 44m

$481

Key WestNassau

EYW - NAS

EYWNAS

Key West

Mon 8/17

12:07 pm-5:10 pm

1 stop5h 03m

Nassau Intl

Sun 8/23

9:55 am-7:13 pm

1 stop9h 18m

$534

Key WestMarsh Harbour

EYW - MHH

EYWMHH

Key West

Tue 9/1

11:30 am-1:17 pm

1 stop25h 47m

Marsh Harbour

Sun 9/6

1:30 pm-7:39 pm

1 stop6h 09m

$568

Key WestMarsh Harbour

EYW - MHH

EYWMHH

Key West

Mon 7/13

7:40 pm-9:33 am

1 stop13h 53m

Marsh Harbour

Fri 7/17

10:13 am-7:06 pm

1 stop8h 53m

$611

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sat 8/15

10:15 am-9:30 am

1 stop23h 15m

Nassau Intl

Sat 8/22

1:28 pm-6:40 pm

1 stop5h 12m

$623

Key WestMarsh Harbour

EYW - MHH

EYWMHH

Key West

Wed 7/29

11:28 am-3:12 pm

1 stop3h 44m

Marsh Harbour

Wed 8/5

11:52 am-7:39 pm

1 stop7h 47m

$627

Key WestRoad Town

EYW - EIS

EYWEIS

Key West

Mon 8/17

10:15 am-4:25 pm

1 stop6h 10m

Road Town Beef Island

Mon 8/24

12:36 pm-7:39 pm

1 stop7h 03m

$802

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 7/16

11:28 am-3:13 pm

1 stop3h 45m

Nassau Intl

Fri 7/17

6:45 pm-1:08 pm

1 stop18h 23m

$854

Key WestNassau

EYW - NAS

EYWNAS

Key West

Tue 9/29

2:15 pm-1:33 pm

1 stop23h 18m

Nassau Intl

Fri 10/2

2:35 pm-1:29 pm

1 stop22h 54m

$893

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/2

Showing 1-10 of 16 resultsSorted by cheapest first
1
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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.
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
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.

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

    For a flight from Key West to Caribbean Islands, you will be flying from Key West. Key West (EYW) is just 2.6 mi from the center of the city.

  • How long is the flight from Key West to Caribbean Islands?

    For as low as $451, American Airlines can have you in Caribbean Islands from Key West in 10h 09m. The distance between Key West and Caribbean Islands is about 1096 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Key West to Caribbean Islands?

    While some choose either Key West - San Juan Luis Munoz Marin Intl or Key West - Road Town Beef Island, Key West - Nassau Intl is the most popular route from Key West to Caribbean Islands.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Key West to Caribbean Islands 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

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Alternative routes for Key West to Caribbean Islands

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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 July 4, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$390Average$519FlexibilityNo cancel feeOn-time71%

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