$152+ Cheap flights from Key West (EYW) to Caribbean
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 10/23. Fares are subject to change and may not be available on all flights or dates of travel.
EYW — SJU
Oct 19 — Oct 261
Round-trip
1 adult, Economy
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Find cheap flights from Key West to Caribbean with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Key West to CaribbeanExplore the most affordable flight options available from Key West to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
Explore the most affordable flight options available from Key West to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2212:01 pm -
1 stop20h 29m
Mon 10/264:00 pm -
2 stops20h 36m
Deal found 9/16![Multiple Airlines logo]()
$530
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/610:59 am -
1 stop5h 16m
Mon 11/94:00 pm -
2 stops20h 36m
Deal found 9/14![Multiple Airlines logo]()
$531
This American Airlines deal was found by Cheapflights users on 9/18. 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 11/211:14 am -
1 stop4h 07m
Mon 11/912:07 pm -
1 stop4h 07m
Deal found 9/18![American Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/232:15 pm -
1 stop9h 35m
Tue 10/276:35 pm -
1 stop19h 19m
Deal found 9/14![United Airlines logo]()
$686
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/271:41 pm -
1 stop27h 34m
Wed 12/27:00 pm -
1 stop15h 48m
Deal found 9/16![American Airlines logo]()
$916
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 9/232:20 pm -
1 stop23h 13m
Sat 9/262:35 pm -
1 stop22h 54m
Deal found 9/15![United Airlines logo]()
$1,023
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/12:15 pm -
2 stops25h 23m
Mon 10/512:20 pm -
2 stops25h 09m
Deal found 9/15![United Airlines logo]()
$1,440
This WestJet deal was found by Cheapflights users on 9/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:40 am -
2 stops31h 50m
Fri 10/163:30 pm -
2 stops27h 31m
Deal found 9/17![WestJet logo]()
$1,711
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/3110:24 am -
1 stop4h 46m
Sat 11/77:00 pm -
2 stops22h 02m
Deal found 9/16![American Airlines logo]()
$1,791
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/132:15 pm -
2 stops48h 40m
Fri 10/162:57 pm -
2 stops45h 32m
Deal found 9/14![United Airlines logo]()
$2,148
Best flights from Key West to CaribbeanDiscover carefully curated flight deals from Key West to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
Discover carefully curated flight deals from Key West to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2212:01 pm -
1 stop20h 29m
Mon 10/264:00 pm -
2 stops20h 36m
Deal found 9/16![Multiple Airlines logo]()
$530
This American Airlines deal was found by Cheapflights users on 9/18. 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 11/211:14 am -
1 stop4h 07m
Mon 11/912:07 pm -
1 stop4h 07m
Deal found 9/18![American Airlines logo]()
$561
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/232:15 pm -
1 stop9h 35m
Tue 10/276:35 pm -
1 stop19h 19m
Deal found 9/14![United Airlines logo]()
$686
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/610:59 am -
1 stop5h 16m
Mon 11/94:00 pm -
2 stops20h 36m
Deal found 9/14![Multiple Airlines logo]()
$531
This American Airlines deal was found by Cheapflights users on 9/14. 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 1/259:52 am -
1 stop3h 24m
Sun 1/3110:28 am -
1 stop8h 35m
Deal found 9/14![American Airlines logo]()
$588
This WestJet deal was found by Cheapflights users on 9/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:40 am -
2 stops31h 50m
Fri 10/163:30 pm -
2 stops27h 31m
Deal found 9/17![WestJet logo]()
$1,711
This American Airlines deal was found by Cheapflights users on 9/16. 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 11/274:43 pm -
1 stop24h 32m
Wed 12/27:00 pm -
2 stops22h 02m
Deal found 9/16![American Airlines logo]()
$920
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Thu 10/12:15 pm -
2 stops25h 23m
Mon 10/512:20 pm -
2 stops25h 09m
Deal found 9/14![United Airlines logo]()
$1,440
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/3110:24 am -
1 stop4h 46m
Sat 11/77:00 pm -
1 stop25h 27m
Deal found 9/16![American Airlines logo]()
$1,795
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/132:15 pm -
2 stops48h 40m
Fri 10/162:57 pm -
2 stops45h 32m
Deal found 9/14![United Airlines logo]()
$2,148
Last-minute flights from Key West to CaribbeanDiscover last-minute flight deals from Key West to Caribbean. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Key West to Caribbean. Data last updated September 19, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 9/232:20 pm -
1 stop23h 13m
Sat 9/262:35 pm -
1 stop22h 54m
Deal found 9/16![United Airlines logo]()
$1,023
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Thu 10/12:15 pm -
2 stops25h 23m
Mon 10/512:20 pm -
2 stops25h 09m
Deal found 9/16![United Airlines logo]()
$1,440
This WestJet deal was found by Cheapflights users on 9/17. 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 WestJet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/137:40 am -
2 stops31h 50m
Fri 10/163:30 pm -
2 stops27h 31m
Deal found 9/17![WestJet logo]()
$1,711
This United Airlines deal was found by Cheapflights users on 9/14. 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.
Tue 10/132:15 pm -
2 stops48h 40m
Fri 10/162:57 pm -
2 stops45h 32m
Deal found 9/14![United Airlines logo]()
$2,148
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2212:01 pm -
1 stop20h 29m
Mon 10/264:00 pm -
2 stops20h 36m
Deal found 9/16![Multiple Airlines logo]()
$530
This United Airlines deal was found by Cheapflights users on 9/14. 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 10/232:15 pm -
1 stop9h 35m
Tue 10/276:35 pm -
1 stop19h 19m
Deal found 9/14![United Airlines logo]()
$686
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/3110:24 am -
1 stop4h 46m
Sat 11/77:00 pm -
2 stops22h 02m
Deal found 9/16![American Airlines logo]()
$1,791
One-way flights from Key West to CaribbeanSearch for one-way flight options from Key West to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
Search for one-way flight options from Key West to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/2310:59 am -
1 stop22h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/16. 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.
Tue 12/110:59 am -
1 stop22h 41m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 9/19. 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 10/510:59 am -
1 stop22h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/19![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/304:09 pm -
2 stops32h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/16![Multiple Airlines logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 9/14. 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 11/99:20 am -
2 stops27h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Multiple Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 9/14. 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 11/97:57 pm -
1 stop21h 23m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![American Airlines logo]()
$493
Find flight deals from Key West to Caribbean
Keep the following information in mind while searching for Key West to Caribbean flight deals. Data was last updated September 19, 2026.
Round-trip from | $530 (Kiwi.com) |
|---|---|
One-way from | $152 (Kiwi.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Key West to Caribbean 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 7,457,451 searches. Data last updated September 19, 2026.
Use the filters below to find and compare flights from Key West to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Mon 10/5
10:59 am-9:35 am
1 stop22h 36m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$191
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Tue 12/1
10:59 am-11:53 am
1 stop23h 54m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$192
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Mon 11/30
4:09 pm-2:07 am
2 stops32h 58m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$214
Key WestRoad Town
EYW Key West - EIS Road Town Beef Island
EYWEIS
Key West
Mon 11/9
11:54 am-6:10 pm
3 stops29h 16m
Road Town Beef Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$410
Key WestRoad Town
EYW Key West - EIS Road Town Beef Island
EYWEIS
Key West
Mon 11/9
7:57 pm-6:20 pm
1 stop21h 23m
Road Town Beef Island
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$493
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Thu 10/22
12:01 pm-8:30 am
1 stop20h 29m
Nassau Intl
Mon 10/26
4:00 pm-12:36 pm
2 stops20h 36m
$530
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Fri 11/6
10:59 am-4:15 pm
1 stop5h 16m
Nassau Intl
Mon 11/9
4:00 pm-12:36 pm
2 stops20h 36m
$531
Quickest round-trip
Key WestMarsh Harbour
EYW Key West - MHH Marsh Harbour
EYWMHH
Key West
Mon 11/2
11:14 am-3:21 pm
1 stop4h 07m
Marsh Harbour
Mon 11/9
12:07 pm-4:14 pm
1 stop4h 07m
$561
Key WestNassau
EYW Key West - NAS Nassau Intl
EYWNAS
Key West
Mon 1/25
9:52 am-1:16 pm
1 stop3h 24m
Nassau Intl
Sun 1/31
10:28 am-7:03 pm
1 stop8h 35m
$588
Key WestSan Juan
EYW Key West - SJU San Juan Luis Munoz Marin Intl
EYWSJU
Key West
Fri 10/23
2:15 pm-11:50 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Tue 10/27
6:35 pm-1:54 pm
1 stop19h 19m
$686
Showing 1-10 of 15 resultsSorted by cheapest first
Best time to book a flight from Key West to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Key West with our price prediction graph.
EYW-SJU
EYW-EIS
EYW-NAS
EYW-KIN
EYW-MHH
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
EYW-0CB
EYW-SJU
EYW-EIS
EYW-NAS
EYW-KIN
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated September 19, 2026.
Read reviews from past customers who have flown American Airlines from Key West to Caribbean. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.2
Overall
7.0
Boarding
7.4
Entertainment
6.8
Crew
7.9
Food
6.4
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Comfort
7.2
Overall
7.0
Boarding
7.4
Entertainment
6.8
Crew
7.9
Food
6.4
Reviews
1 / 20
8.0
ExcellentOlwin,Jul 2026
MCO - DCA
Related info for your journey
Find useful and relevant information for your journey from Key West to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Key West to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Key West to Caribbean by cabin class
Find flights from Key West to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Key West and Caribbean flights
Browse other Key West and Caribbean flight options. Last updated on September 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Key West to Caribbean flights
Consider these flights traveling from Key West to Caribbean.
Top airline flying from Key West to Caribbean
Discover the top airline that operate flights from Key West to Caribbean. 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 7,457,451 searches. Data last updated September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$415 | Average$586 | FlexibilityNo cancel fee | On-time71% |