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Caribbean Islands

$132+ 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 1/25. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Jan 31 — Feb 71
Sat 1/31
Sat 2/7
1 adult, Economy
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Cheap flight deals from Key West to Caribbean Islands

Best flights from Key West to Caribbean Islands
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 January 1, 2026.

This Kiwi.com deal was found by Cheapflights users on 12/31. 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 1/239:49 amEYW - SJU
1 stop13h 10mMultiple Airlines
Thu 1/294:22 pmSJU - EYW
2 stops17h 47mMultiple Airlines
Deal found 12/31$292
This Mytrip deal was found by Cheapflights users on 12/31. 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 1/232:25 pmEYW - SJU
3 stops27h 24mSpirit Airlines
Thu 1/295:50 pmSJU - EYW
2 stops20h 40mSpirit Airlines
Deal found 12/31$367
This American Airlines deal was found by Cheapflights users on 12/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/147:36 pmEYW - SJU
1 stop15h 20mAmerican Airlines
Sun 2/227:00 amSJU - EYW
1 stop10h 49mAmerican Airlines
Deal found 12/30$385
This Delta deal was found by Cheapflights users on 12/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/197:10 amEYW - NAS
1 stop9h 52mDelta
Mon 2/231:15 pmNAS - EYW
1 stop6h 27mDelta
Deal found 12/30$488
This American Airlines deal was found by Cheapflights users on 12/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/167:42 pmEYW - SJU
1 stop13h 18mAmerican Airlines
Sat 3/217:11 amSJU - EYW
1 stop8h 27mAmerican Airlines
Deal found 12/30$390
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 1/1410:49 amEYW - SJU
2 stops24h 43mMultiple Airlines
Mon 1/196:00 amSJU - EYW
1 stop7h 26mMultiple Airlines
Deal found 12/31$430
This Kiwi.com deal was found by Cheapflights users on 12/31. 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 2/152:25 pmEYW - NAS
1 stop4h 50mMultiple Airlines
Tue 3/1712:00 pmNAS - EYW
1 stop23h 11mMultiple Airlines
Deal found 12/31$478
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Thu 2/199:46 amEYW - NAS
1 stop6h 39mMultiple Airlines
Sun 2/2212:00 pmNAS - EYW
1 stop24h 26mMultiple Airlines
Deal found 12/30$481
This American Airlines deal was found by Cheapflights users on 12/31. 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 1/244:37 pmEYW - NAS
1 stop25h 18mAmerican Airlines
Mon 1/266:45 pmNAS - EYW
1 stop5h 11mAmerican Airlines
Deal found 12/31$540
This Delta deal was found by Cheapflights users on 12/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:00 amEYW - KIN
1 stop14h 05mDelta
Mon 5/119:00 amKIN - EYW
1 stop9h 44mDelta
Deal found 12/29$621
This Kiwi.com deal was found by Cheapflights users on 12/30. 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.
Thu 2/199:46 amEYW - NAS
1 stop6h 39mMultiple Airlines
Mon 2/234:00 pmNAS - EYW
2 stops20h 21mMultiple Airlines
Deal found 12/30$488
This American Airlines deal was found by Cheapflights users on 1/1. 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.
Thu 2/191:55 pmEYW - NAS
1 stop5h 56mAmerican Airlines
Sun 2/228:06 amNAS - EYW
1 stop5h 09mAmerican Airlines
Deal found 1/1$555
This Kiwi.com deal was found by Cheapflights users on 12/30. 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 2/23:52 pmEYW - NAS
2 stops22h 53mMultiple Airlines
Fri 2/67:15 amNAS - EYW
1 stop6h 15mMultiple Airlines
Deal found 12/30$514
This United Airlines deal was found by Cheapflights users on 12/28. 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 5/314:05 pmEYW - KIN
2 stops46h 49mUnited Airlines
Thu 6/42:59 pmKIN - EYW
2 stops30h 12mUnited Airlines
Deal found 12/28$1,830
This American Airlines deal was found by Cheapflights users on 12/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/43:20 pmEYW - MHH
1 stop24h 10mAmerican Airlines
Sat 4/111:55 pmMHH - EYW
1 stop9h 02mAmerican Airlines
Deal found 12/30$985
This American Airlines deal was found by Cheapflights users on 12/31. 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 2/143:51 pmEYW - EIS
1 stop5h 24mAmerican Airlines
Sat 2/219:20 amEIS - EYW
1 stop10h 34mAmerican Airlines
Deal found 12/31$993

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 January 1, 2026.

Round-trip from

$292
(Kiwi.com)

One-way from

$132
(Kiwi.com)
From Key West to Caribbean Islands
Search Deals
One-way flight 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 January 1, 2026.
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 1/23

9:49 am-11:59 pm

1 stop13h 10m

San Juan Luis Munoz Marin Intl

Thu 1/29

4:22 pm-9:09 am

2 stops17h 47m

$292

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 1/23

2:25 pm-6:49 pm

3 stops27h 24m

San Juan Luis Munoz Marin Intl

Thu 1/29

5:50 pm-1:30 pm

2 stops20h 40m

$367

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Sat 2/14

7:36 pm-11:56 am

1 stop15h 20m

San Juan Luis Munoz Marin Intl

Sun 2/22

7:00 am-4:49 pm

1 stop10h 49m

$385

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Mon 3/16

7:42 pm-9:00 am

1 stop13h 18m

San Juan Luis Munoz Marin Intl

Sat 3/21

7:11 am-3:38 pm

1 stop8h 27m

$390

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Wed 1/14

10:49 am-12:32 pm

2 stops24h 43m

San Juan Luis Munoz Marin Intl

Mon 1/19

6:00 am-12:26 pm

1 stop7h 26m

$430

Key WestNassau

EYW - NAS

EYWNAS

Key West

Sun 2/15

2:25 pm-7:15 pm

1 stop4h 50m

Nassau Intl

Tue 3/17

12:00 pm-11:11 am

1 stop23h 11m

$478

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 2/19

9:46 am-4:25 pm

1 stop6h 39m

Nassau Intl

Sun 2/22

12:00 pm-12:26 pm

1 stop24h 26m

$481

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 2/19

7:10 am-5:02 pm

1 stop9h 52m

Nassau Intl

Mon 2/23

1:15 pm-7:42 pm

1 stop6h 27m

$488

Key WestNassau

EYW - NAS

EYWNAS

Key West

Thu 2/19

9:46 am-4:25 pm

1 stop6h 39m

Nassau Intl

Mon 2/23

4:00 pm-12:21 pm

2 stops20h 21m

$488

Key WestNassau

EYW - NAS

EYWNAS

Key West

Mon 2/2

3:52 pm-2:45 pm

2 stops22h 53m

Nassau Intl

Fri 2/6

7:15 am-1:30 pm

1 stop6h 15m

$514

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/30

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
No data available for this route at this time. Please check back soon.

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 January 1, 2026.
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
11,069 reviews

Crew

8.0

Boarding

7.5

Food

6.4

Overall

7.2

Entertainment

6.9

Comfort

7.2

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
11,069 reviews
American Airlines
7.2
Good
11,069 reviews

Crew

8.0

Boarding

7.5

Food

6.4

Overall

7.2

Entertainment

6.9

Comfort

7.2

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 $488, Spirit Airlines can have you in Caribbean Islands from Key West in 9h 52m. 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.

See more FAQs

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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 January 1, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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