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Caribbean Islands

$322+ 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 2/20. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
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 December 12, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Fri 12/262:30 pmEYW - SJU
1 stop6h 35mMultiple Airlines
Sat 1/34:10 amSJU - EYW
2 stops7h 09mMultiple Airlines
Deal found 12/10$454
This WAYA deal was found by Cheapflights users on 12/10. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/262:30 pmEYW - SJU
1 stop6h 35mSpirit Airlines
Sat 1/34:10 amSJU - EYW
1 stop8h 10mSpirit Airlines
Deal found 12/10$456
This Kiwi.com deal was found by Cheapflights users on 12/10. 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.
Sat 12/272:30 pmEYW - NAS
1 stop4h 45mMultiple Airlines
Wed 12/317:15 amNAS - EYW
1 stop6h 15mMultiple Airlines
Deal found 12/10$574
This Kiwi.com deal was found by Cheapflights users on 12/10. 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 12/242:30 pmEYW - NAS
1 stop4h 45mMultiple Airlines
Sat 12/274:00 pmNAS - EYW
1 stop19h 20mMultiple Airlines
Deal found 12/10$589
This Expedia deal was found by Cheapflights users on 12/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/271:12 pmEYW - NAS
2 stops20h 08mJetBlue
Wed 12/312:47 pmNAS - EYW
2 stops21h 30mJetBlue
Deal found 12/10$1,341

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 December 12, 2025.

Round-trip from

$322
(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 December 12, 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 2/20

9:49 am-2:25 am

1 stop15h 36m

San Juan Luis Munoz Marin Intl

Fri 2/27

2:54 am-10:21 am

2 stops32h 27m

$322

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Sat 2/14

7:35 pm-11:55 am

1 stop15h 20m

San Juan Luis Munoz Marin Intl

Sun 2/22

7:00 am-10:58 am

1 stop4h 58m

$365

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Tue 1/13

7:08 am-6:22 pm

2 stops10h 14m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:00 am-1:03 pm

1 stop8h 03m

$425

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 4/24

12:13 pm-7:55 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Mon 4/27

6:25 am-6:21 pm

1 stop11h 56m

$445

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 12/26

2:30 pm-10:05 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Sat 1/3

4:10 am-10:19 am

2 stops7h 09m

$454

Key WestSan Juan

EYW - SJU

EYWSJU

Key West

Fri 12/26

2:30 pm-10:05 pm

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Sat 1/3

4:10 am-11:20 am

1 stop8h 10m

$456

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 2/13

7:10 am-5:02 pm

1 stop9h 52m

Nassau Intl

Tue 2/17

1:15 pm-7:42 pm

1 stop6h 27m

$471

Key WestNassau

EYW - NAS

EYWNAS

Key West

Fri 2/13

7:10 am-5:02 pm

1 stop9h 52m

Nassau Intl

Wed 2/18

1:15 pm-7:42 pm

1 stop6h 27m

$471

Key WestNassau

EYW - NAS

EYWNAS

Key West

Mon 2/2

1:33 pm-5:55 pm

1 stop4h 22m

Nassau Intl

Fri 2/6

11:58 am-4:49 pm

1 stop4h 51m

$475

Key WestNassau

EYW - NAS

EYWNAS

Key West

Mon 2/16

2:25 pm-7:15 pm

1 stop4h 50m

Nassau Intl

Thu 2/19

7:15 am-11:17 am

1 stop4h 02m

$481

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 22 results
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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

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 December 12, 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 15% 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 December 12, 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

Food

6.5

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

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
11,050 reviews
American Airlines
7.2
Good
11,050 reviews

Food

6.5

Comfort

7.2

Crew

8.0

Boarding

7.5

Entertainment

6.9

Overall

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 $471, American 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 - 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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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 December 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$360Average$526FlexibilityNo cancel feeOn-time71%

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