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Caribbean Islands

$142+ 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 12/27. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Cheap 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 November 13, 2025.

Round-trip from

$412
(Kiwi.com)

One-way from

$142
(Kiwi.com)
From Key West to Caribbean Islands
Search Deals
One-way flight from Key West to Caribbean Islands
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Find 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 November 13, 2025.

This Kiwi.com deal was found by Cheapflights users on 11/13. 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.
Fri 11/289:57 amEYW - SJU
1 stop12h 12mMultiple Airlines
Tue 12/29:15 amSJU - EYW
2 stops25h 52mMultiple Airlines
Deal found 11/13$412
This Kiwi.com deal was found by Cheapflights users on 11/12. 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.
Sat 12/62:30 pmEYW - NAS
1 stop4h 45mMultiple Airlines
Sat 12/134:00 pmNAS - EYW
1 stop19h 20mMultiple Airlines
Deal found 11/12$473
This American Airlines deal was found by Cheapflights users on 11/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/287:00 amEYW - SJU
1 stop8h 06mAmerican Airlines
Tue 12/22:50 pmSJU - EYW
1 stop5h 33mAmerican Airlines
Deal found 11/13$525
This Mytrip deal was found by Cheapflights users on 11/11. 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.
Fri 12/262:30 pmEYW - NAS
1 stop4h 45mMultiple Airlines
Fri 1/27:15 amNAS - EYW
1 stop6h 15mMultiple Airlines
Deal found 11/11$533
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Sun 12/288:09 pmEYW - SJU
1 stop12h 26mAmerican Airlines
Fri 1/210:25 amSJU - EYW
1 stop10h 14mAmerican Airlines
Deal found 11/11$615
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Sat 11/157:53 pmEYW - KIN
1 stop16h 46mAmerican Airlines
Mon 11/171:40 pmKIN - EYW
1 stop5h 43mAmerican Airlines
Deal found 11/11$861
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Mon 12/298:00 amEYW - SJU
2 stops9h 07mAmerican Airlines
Mon 1/512:47 pmSJU - EYW
1 stop4h 57mAmerican Airlines
Deal found 11/12$865
This United Airlines deal was found by Cheapflights users on 11/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/283:09 pmEYW - SJU
1 stop8h 27mUnited Airlines
Thu 1/12:05 amSJU - EYW
2 stops14h 43mUnited Airlines
Deal found 11/11$910
This United Airlines deal was found by Cheapflights users on 11/13. 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.
Fri 11/282:42 pmEYW - SJU
2 stops21h 35mUnited Airlines
Tue 12/28:30 amSJU - EYW
2 stops31h 54mUnited Airlines
Deal found 11/13$1,035
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Tue 12/27:00 amEYW - EIS
1 stop9h 06mAmerican Airlines
Sun 12/75:48 pmEIS - EYW
1 stop6h 19mAmerican Airlines
Deal found 11/11$1,098
This JetBlue deal was found by Cheapflights users on 11/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/281:12 pmEYW - SJU
1 stop9h 44mJetBlue
Thu 1/12:05 amSJU - EYW
1 stop11h 12mJetBlue
Deal found 11/11$1,417
This KAYAK deal was found by Cheapflights users on 11/12. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/291:12 pmEYW - SJU
1 stop9h 44mJetBlue
Sun 1/42:05 amSJU - EYW
1 stop11h 12mJetBlue
Deal found 11/12$1,622

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 November 13, 2025.
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

Fri 11/28

9:57 am-11:09 pm

1 stop12h 12m

San Juan Luis Munoz Marin Intl

Tue 12/2

9:15 am-10:07 am

2 stops25h 52m

$412

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 5/8

2:02 pm-6:35 pm

1 stop4h 33m

Nassau Intl

Wed 5/20

9:50 am-4:21 pm

1 stop6h 31m

$472

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sat 12/6

2:30 pm-7:15 pm

1 stop4h 45m

Nassau Intl

Sat 12/13

4:00 pm-11:20 am

1 stop19h 20m

$473

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 1/8

7:10 am-5:00 pm

1 stop9h 50m

Nassau Intl

Mon 1/12

1:15 pm-7:42 pm

1 stop6h 27m

$488

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Tue 3/10

8:10 am-8:36 am

2 stops24h 26m

San Juan Luis Munoz Marin Intl

Wed 3/11

5:45 pm-4:05 pm

2 stops22h 20m

$514

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 11/28

7:00 am-4:06 pm

1 stop8h 06m

San Juan Luis Munoz Marin Intl

Tue 12/2

2:50 pm-7:23 pm

1 stop5h 33m

$525

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 12/26

2:30 pm-7:15 pm

1 stop4h 45m

Nassau Intl

Fri 1/2

7:15 am-1:30 pm

1 stop6h 15m

$533

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Sun 12/28

8:09 pm-9:35 am

1 stop12h 26m

San Juan Luis Munoz Marin Intl

Fri 1/2

10:25 am-7:39 pm

1 stop10h 14m

$615

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Mon 12/29

8:09 pm-9:35 am

1 stop12h 26m

San Juan Luis Munoz Marin Intl

Mon 1/5

5:24 am-1:13 pm

1 stop8h 49m

$615

Key WestMarsh Harbour

EYW - MHH

EYWMHH

Key West

Sun 3/22

6:31 am-5:10 pm

1 stop10h 39m

Marsh Harbour

Wed 3/25

2:50 pm-11:59 pm

1 stop9h 09m

$627

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/12

Showing 1-10 of 19 results
1
2

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

What is the cheapest time of day to fly from EYW to EPX?

Find hourly flight availability from Key West to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

One of the essential ways to save on airfare from Key West to Caribbean Islands is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 12% on airfare.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated November 13, 2025.
Get a feel of what it's like to fly with American Airlines from Key West to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.2
Good
11,050 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Boarding

7.5

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.
American Airlines
7.2
Good
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Comfort

7.2

Overall

7.2

Crew

8.0

Boarding

7.5

Food

6.4

Entertainment

6.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

MIA - DCA

Flight delayed 5 hours and was told it was due to mechanical issues. Instead of providing lodging due to missed connecting flight, American changed the cause of delay to weather, which meant they were not able required to provide a hotel. To make matters worse, one of our checked bags was lost even though its status said it was “by the plane” but no one at the service desk seemed able to locate it.

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 $472, American Airlines can have you in Caribbean Islands from Key West in 4h 33m. The distance between Key West and Caribbean Islands is about 271 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 - Nassau Intl or Key West - Road Town Beef Island, Key West - San Juan Luis Munoz Marin 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.

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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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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