$66+ Cheap flights from Clearwater, FL to Caribbean
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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — SJU
Mar 1 — Mar 81
1 adult, Economy
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Find cheap flights from Clearwater to Caribbean with Cheapflights
1. Tell us where you want to go
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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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Clearwater to Caribbean
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Cheapest flights from Clearwater to CaribbeanExplore the most affordable flight options available from Clearwater to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2026.
Explore the most affordable flight options available from Clearwater to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 30, 2026.
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:30 am
TPA
- STX
1 stop6h 10m
Spirit Airlines
Sat 2/284:37 pm
STX
- TPA
1 stop5h 23m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$137
This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:30 am
TPA
- STT
1 stop7h 04m
Spirit Airlines
Sat 3/144:35 pm
STT
- TPA
1 stop5h 24m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$152
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:30 am
TPA
- STX
1 stop6h 10m
Spirit Airlines
Sat 3/74:37 pm
STX
- TPA
1 stop5h 23m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$164
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:30 am
TPA
- SJU
1 stop6h 01m
Spirit Airlines
Tue 3/34:31 pm
SJU
- TPA
1 stop5h 29m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$177
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:15 am
TPA
- SJU
1 stop7h 51m
Multiple Airlines
Sun 3/17:00 am
SJU
- TPA
Nonstop3h 20m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
TPA
- SJU
1 stop16h 24m
Multiple Airlines
Mon 2/237:00 am
SJU
- TPA
Nonstop3h 20m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$179
This Frontier deal was found by Cheapflights users on 1/28. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/88:05 pm
TPA
- SJU
Nonstop2h 57m
Frontier
Mon 5/117:15 am
SJU
- TPA
Nonstop3h 20m
Frontier
Deal found 1/28![Frontier logo]()
$180
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:54 pm
TPA
- SJU
1 stop12h 55m
Multiple Airlines
Tue 4/142:09 pm
SJU
- TPA
Nonstop3h 25m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$181
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:25 am
TPA
- SJU
Nonstop3h 00m
Spirit Airlines
Mon 3/27:00 am
SJU
- TPA
Nonstop3h 20m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$182
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:30 am
TPA
- STT
1 stop7h 04m
Spirit Airlines
Wed 3/114:40 pm
STT
- TPA
1 stop6h 06m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$182
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:15 am
TPA
- SJU
1 stop7h 51m
Multiple Airlines
Tue 3/37:00 am
SJU
- TPA
Nonstop3h 20m
Multiple Airlines
Deal found 1/30![Multiple Airlines logo]()
$183
This Frontier deal was found by Cheapflights users on 1/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:45 am
TPA
- SJU
Nonstop2h 57m
Frontier
Sun 5/31:59 am
SJU
- TPA
1 stop11h 34m
Frontier
Deal found 1/29![Frontier logo]()
$184
Best flights from Clearwater to CaribbeanDiscover carefully curated flight deals from Clearwater to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 30, 2026.
Discover carefully curated flight deals from Clearwater to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 30, 2026.
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:30 am
TPA
- STX
1 stop6h 10m
Spirit Airlines
Sat 2/284:37 pm
STX
- TPA
1 stop5h 23m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$137
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/79:00 am
TPA
- SJU
1 stop14h 54m
Frontier
Mon 4/132:31 pm
SJU
- TPA
1 stop8h 49m
Frontier
Deal found 1/27![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:00 am
TPA
- SJU
Nonstop2h 59m
Multiple Airlines
Tue 5/53:36 pm
SJU
- TPA
1 stop6h 23m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$218
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/166:10 am
TPA
- SJU
Nonstop3h 00m
Southwest
Sat 6/206:30 am
SJU
- TPA
Nonstop3h 05m
Southwest
Deal found 1/28![Southwest logo]()
$245
This KAYAK deal was found by Cheapflights users on 1/29. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/48:00 am
TPA
- SDQ
1 stop5h 18m
JetBlue
Wed 3/49:43 pm
SDQ
- TPA
1 stop11h 33m
JetBlue
Deal found 1/29![JetBlue logo]()
$245
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/93:48 pm
TPA
- SJU
1 stop7h 06m
Delta
Wed 5/137:30 am
SJU
- TPA
1 stop7h 15m
Delta
Deal found 1/28![Delta logo]()
$254
This American Airlines deal was found by Cheapflights users on 1/29. 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 2/266:00 am
TPA
- STX
1 stop10h 37m
American Airlines
Tue 3/36:27 pm
STX
- TPA
1 stop6h 32m
American Airlines
Deal found 1/29![American Airlines logo]()
$264
This Copa Airlines deal was found by Cheapflights users on 1/28. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:24 am
TPA
- AUA
1 stop6h 44m
Copa Airlines
Thu 4/167:06 am
AUA
- TPA
1 stop6h 36m
Copa Airlines
Deal found 1/28![Copa Airlines logo]()
$283
This Breeze Airways deal was found by Cheapflights users on 1/29. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/97:25 am
TPA
- NAS
Nonstop1h 30m
Breeze Airways
Thu 7/169:55 am
NAS
- TPA
Nonstop1h 30m
Breeze Airways
Deal found 1/29![Breeze Airways logo]()
$300
This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:30 am
TPA
- STT
1 stop7h 04m
Spirit Airlines
Sat 3/144:35 pm
STT
- TPA
1 stop5h 24m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$152
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/234:30 pm
TPA
- GCM
Nonstop1h 50m
Cayman Airways
Mon 4/2712:40 pm
GCM
- TPA
Nonstop1h 50m
Cayman Airways
Deal found 1/28![Cayman Airways logo]()
$318
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:30 am
TPA
- STX
1 stop6h 10m
Spirit Airlines
Sat 3/74:37 pm
STX
- TPA
1 stop5h 23m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$164
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/28:30 am
TPA
- STT
1 stop7h 04m
Spirit Airlines
Wed 3/114:40 pm
STT
- TPA
1 stop6h 06m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:30 am
TPA
- STX
1 stop6h 10m
Multiple Airlines
Sat 3/74:37 pm
STX
- TPA
2 stops31h 49m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$233
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/238:14 am
TPA
- STT
1 stop7h 14m
Spirit Airlines
Mon 3/304:35 pm
STT
- TPA
1 stop5h 24m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$182
This Southwest deal was found by Cheapflights users on 1/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/198:35 pm
TPA
- SJU
Nonstop3h 00m
Southwest
Thu 6/257:00 am
SJU
- TPA
Nonstop3h 05m
Southwest
Deal found 1/28![Southwest logo]()
$245
This Delta deal was found by Cheapflights users on 1/29. 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.
Sat 5/22:45 pm
TPA
- SJU
1 stop8h 28m
Delta
Wed 5/66:15 am
SJU
- TPA
1 stop8h 33m
Delta
Deal found 1/29![Delta logo]()
$254
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
TPA
- STX
1 stop10h 37m
American Airlines
Tue 3/105:17 pm
STX
- TPA
1 stop6h 42m
American Airlines
Deal found 1/28![American Airlines logo]()
$264
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:00 pm
TPA
- SJU
Nonstop3h 00m
Southwest
Sat 7/116:30 am
SJU
- TPA
Nonstop3h 05m
Southwest
Deal found 1/29![Southwest logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:59 am
TPA
- SJU
1 stop4h 32m
Multiple Airlines
Mon 5/44:11 pm
SJU
- TPA
1 stop6h 51m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$252
This Delta deal was found by Cheapflights users on 1/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:20 am
TPA
- SJU
1 stop10h 03m
Delta
Tue 4/286:15 am
SJU
- TPA
1 stop8h 33m
Delta
Deal found 1/28![Delta logo]()
$254
This Copa Airlines deal was found by Cheapflights users on 1/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/243:29 pm
TPA
- AUA
1 stop6h 28m
Copa Airlines
Sun 5/317:19 am
AUA
- TPA
1 stop15h 46m
Copa Airlines
Deal found 1/29![Copa Airlines logo]()
$283
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:30 am
TPA
- STT
1 stop7h 04m
Spirit Airlines
Fri 2/275:40 pm
STT
- TPA
1 stop14h 55m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:35 pm
TPA
- SXM
1 stop17h 41m
American Airlines
Mon 3/164:01 pm
SXM
- TPA
1 stop17h 49m
American Airlines
Deal found 1/28![American Airlines logo]()
$271
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/56:10 am
TPA
- SJU
Nonstop2h 45m
Southwest
Sat 4/186:25 pm
SJU
- TPA
Nonstop3h 10m
Southwest
Deal found 1/29![Southwest logo]()
$251
This SmartFares deal was found by Cheapflights users on 1/27. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2011:42 am
TPA
- PUJ
Nonstop2h 36m
JetBlue
Mon 3/303:23 pm
PUJ
- TPA
Nonstop3h 02m
JetBlue
Deal found 1/27![JetBlue logo]()
$306
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:30 am
TPA
- STX
1 stop6h 10m
Multiple Airlines
Sat 2/284:37 pm
STX
- TPA
2 stops20h 20m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$257
This Copa Airlines deal was found by Cheapflights users on 1/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/12:39 pm
TPA
- AUA
1 stop6h 20m
Copa Airlines
Sun 3/157:05 am
AUA
- TPA
1 stop16h 00m
Copa Airlines
Deal found 1/29![Copa Airlines logo]()
$283
This CheapOair deal was found by Cheapflights users on 1/30. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:30 am
TPA
- STT
1 stop7h 04m
Spirit Airlines
Mon 3/25:40 pm
STT
- TPA
1 stop14h 55m
Spirit Airlines
Deal found 1/30![Spirit Airlines logo]()
$194
This American Airlines deal was found by Cheapflights users on 1/29. 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.
Sat 4/256:00 am
TPA
- SXM
1 stop5h 37m
American Airlines
Wed 4/292:24 pm
SXM
- TPA
1 stop9h 47m
American Airlines
Deal found 1/29![American Airlines logo]()
$271
Last-minute flights from Clearwater to CaribbeanDiscover last-minute flight deals from Clearwater to Caribbean. Data last updated January 30, 2026 and is based on user searches.
Discover last-minute flight deals from Clearwater to Caribbean. Data last updated January 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1310:34 pm
TPA
- SJU
Nonstop2h 51m
Frontier
Fri 2/202:54 am
SJU
- TPA
1 stop16h 37m
Frontier
Deal found 1/29![Frontier logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/148:30 am
TPA
- SJU
2 stops16h 55m
Multiple Airlines
Wed 2/254:31 pm
SJU
- TPA
1 stop5h 29m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$181
This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/188:30 am
TPA
- SJU
1 stop6h 01m
Multiple Airlines
Fri 2/202:54 am
SJU
- TPA
1 stop16h 37m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$186
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/2010:34 pm
TPA
- SJU
Nonstop2h 51m
Multiple Airlines
Wed 2/257:00 am
SJU
- TPA
Nonstop3h 20m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:30 am
TPA
- STX
1 stop6h 10m
Spirit Airlines
Sat 3/74:37 pm
STX
- TPA
1 stop5h 23m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/218:00 am
TPA
- SJU
1 stop16h 24m
Multiple Airlines
Mon 2/237:00 am
SJU
- TPA
Nonstop3h 20m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$179
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:30 am
TPA
- STX
1 stop6h 10m
Spirit Airlines
Sat 2/284:37 pm
STX
- TPA
1 stop5h 23m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 1/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/248:30 am
TPA
- SJU
1 stop6h 01m
Spirit Airlines
Wed 2/256:00 am
SJU
- TPA
2 stops13h 03m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$180
This CheapOair deal was found by Cheapflights users on 1/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/246:15 am
TPA
- SJU
1 stop7h 51m
Multiple Airlines
Tue 3/37:00 am
SJU
- TPA
Nonstop3h 20m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$183
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:15 am
TPA
- SJU
1 stop7h 51m
Multiple Airlines
Sun 3/17:00 am
SJU
- TPA
Nonstop3h 20m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$178
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2510:25 am
TPA
- SJU
Nonstop3h 00m
Spirit Airlines
Mon 3/27:00 am
SJU
- TPA
Nonstop3h 20m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$182
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:30 am
TPA
- SJU
1 stop6h 01m
Spirit Airlines
Tue 3/34:31 pm
SJU
- TPA
1 stop5h 29m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$177
One-way flights from Clearwater to CaribbeanSearch for one-way flight options from Clearwater to Caribbean. Find affordable one-way fares based on user searches. Data last updated January 30, 2026.
Search for one-way flight options from Clearwater to Caribbean. Find affordable one-way fares based on user searches. Data last updated January 30, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:30 am
TPA
- AUA
1 stop6h 05m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$66
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/79:47 pm
TPA
- SXM
1 stop15h 28m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$71
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:30 am
TPA
- STT
1 stop7h 04m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$74
This Trip.com deal was found by Cheapflights users on 1/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/79:24 am
TPA
- NAS
1 stop7h 45m
Frontier
Deal found 1/28![Frontier logo]()
$81
This Priceline deal was found by Cheapflights users on 1/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/98:14 am
TPA
- GCM
1 stop5h 43m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$83
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1110:05 am
TPA
- STT
1 stop5h 32m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$83
This Priceline deal was found by Cheapflights users on 1/27. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1010:05 am
TPA
- SJU
1 stop4h 30m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$89
This Kiwi.com deal was found by Cheapflights users on 1/30. 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.
Fri 4/2411:45 am
TPA
- SJU
Nonstop2h 57m
Frontier
Deal found 1/30![Frontier logo]()
$90
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/268:30 am
TPA
- AUA
1 stop6h 05m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$91
This Frontier deal was found by Cheapflights users on 1/30. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/178:05 pm
TPA
- SJU
Nonstop2h 57m
Frontier
Deal found 1/30![Frontier logo]()
$91
This Delta deal was found by Cheapflights users on 1/29. 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.
Sat 2/285:25 am
TPA
- GCM
1 stop5h 35m
Delta
Deal found 1/29![Delta logo]()
$91
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
TPA
- SXM
1 stop7h 16m
American Airlines
Deal found 1/28![American Airlines logo]()
$91
Find flight deals from Clearwater to Caribbean
Keep the following information in mind while searching for Clearwater to Caribbean flight deals. Data was last updated January 30, 2026.
Round-trip from | $141 (Expedia) |
|---|---|
One-way from | $66 (Cheapflightsfares) |
Popular in | December |
Cheapest in | February |
Average price | $256 |
Cheapflights Fare Finder
Customize your flight search to find flights from Clearwater 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 2,558,603 searches. Data last updated January 30, 2026.
Use the filters below to find and compare flights from Clearwater to Caribbean that are best for you.
Fly from
Clearwater
Fly to
Caribbean
Route
Depart
Return
Price
TampaChristiansted
TPA - STX
TPASTX
Tampa
Mon 2/23
8:30 am-3:40 pm
1 stop6h 10m
Christiansted Henry Rohlsen
Sat 2/28
4:37 pm-9:00 pm
1 stop5h 23m
$137
TampaSaint Thomas Island
TPA - STT
TPASTT
Tampa
Sat 3/7
8:30 am-4:34 pm
1 stop7h 04m
Saint Thomas Island Cyril E King
Sat 3/14
4:35 pm-9:59 pm
1 stop5h 24m
$152
TampaChristiansted
TPA - STX
TPASTX
Tampa
Sat 2/21
8:30 am-3:40 pm
1 stop6h 10m
Christiansted Henry Rohlsen
Sat 3/7
4:37 pm-9:00 pm
1 stop5h 23m
$164
TampaSaint Thomas Island
TPA - STT
TPASTT
Tampa
Mon 3/2
8:30 am-4:34 pm
1 stop7h 04m
Saint Thomas Island Cyril E King
Wed 3/11
4:40 pm-10:46 pm
1 stop6h 06m
$182
TampaSaint Thomas Island
TPA - STT
TPASTT
Tampa
Mon 3/23
8:14 am-3:28 pm
1 stop7h 14m
Saint Thomas Island Cyril E King
Mon 3/30
4:35 pm-9:59 pm
1 stop5h 24m
$182
TampaSaint Thomas Island
TPA - STT
TPASTT
Tampa
Mon 2/23
8:30 am-4:34 pm
1 stop7h 04m
Saint Thomas Island Cyril E King
Fri 2/27
5:40 pm-7:35 am
1 stop14h 55m
$194
TampaSaint Thomas Island
TPA - STT
TPASTT
Tampa
Mon 2/23
8:30 am-4:34 pm
1 stop7h 04m
Saint Thomas Island Cyril E King
Mon 3/2
5:40 pm-7:35 am
1 stop14h 55m
$194
TampaSan Juan
TPA - SJU
TPASJU
Tampa
Tue 4/7
9:00 am-11:54 pm
1 stop14h 54m
San Juan Luis Munoz Marin Intl
Mon 4/13
2:31 pm-11:20 pm
1 stop8h 49m
$214
TampaSan Juan
TPA - SJU
TPASJU
Tampa
Tue 4/28
10:00 am-12:59 pm
Nonstop2h 59m
San Juan Luis Munoz Marin Intl
Tue 5/5
3:36 pm-9:59 pm
1 stop6h 23m
$218
TampaChristiansted
TPA - STX
TPASTX
Tampa
Sat 2/21
8:30 am-3:40 pm
1 stop6h 10m
Christiansted Henry Rohlsen
Sat 3/7
4:37 pm-11:26 pm
2 stops31h 49m
$233
Showing 1-10 of 60 results
Best time to book a flight from Clearwater to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Clearwater with our price prediction graph.
TPA-STX
TPA-SJU
TPA-SDQ
TPA-AUA
TPA-NAS
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 Clearwater to Caribbean
CL9-0CB
TPA-STX
TPA-SJU
TPA-SDQ
TPA-AUA
What is the cheapest month to book a flight from Clearwater to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Clearwater to Caribbean (average of $53). Flying from Clearwater to Caribbean in November is currently the most expensive (average of $113). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CL9 to CB?
Find hourly flight availability from Clearwater to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 30, 2026.
A simple way to save on the total cost of your ticket is to fly from Clearwater to Caribbean in the afternoon. If you’re flexible enough to do this you can expect to save up to 20% on your trip compared to booking a flight in the morning.
What is the cheapest day to fly from Clearwater to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Clearwater to Caribbean. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Clearwater to Caribbean flight should consider departing on Sunday afternoons when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Clearwater to Caribbean
Explore weekly flight availability from Clearwater to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated January 30, 2026.
The most flights from CL9 to 0CB are scheduled on a Friday (19 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (8 on average).
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 January 30, 2026.
See what other customers who have flown with Southwest, American Airlines, and JetBlue from Clearwater to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Overall
8.0
Comfort
8.0
Reviews
1 / 20
2.0
MediocreThomas,Dec 2025
SEA - DEN
Related info for your journey
Find useful and relevant information for your journey from Clearwater to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes for Clearwater to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 10 airlines flying from Clearwater to Caribbean
Discover the top 10 airlines that operate flights from Clearwater 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 2,558,603 searches. Data last updated January 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$66 | Average$197 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$78 | Average$358 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$89 | Average$307 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$94 | Average$449 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$99 | Average$298 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$103 | Average$416 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$328 | FlexibilityNo cancel fee | On-time33% | |
| Cheapest$163 | Average$477 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$164 | Average$395 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$202 | Average$232 | FlexibilityNo cancel fee | On-timeN/A |