$96 Find Cheap Flights from Tampa to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tampa to Caribbean Islands departing on 7/27. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tampa to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tampa to Caribbean Islands.
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Cheap Flights from Tampa to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$322
Santo Domingo
Santo Domingo1 stop$321
Montego Bay
Montego Bay1 stop$306
Oranjestad
Oranjestad1 stop$346
Nassau
Nassaunonstop$300
Kingston
Kingston1 stop$381
Simpson Bay
Simpson Bay1 stop$341
Providenciales
Providenciales1 stop$559
Port of Spain
Port of Spain1 stop$529
Bridgetown
Bridgetown1 stop$448
George Town
George Townnonstop$327
Willemstad
Willemstad1 stop$520
Castries
Castries2 stops$1,028
Aguadilla
Aguadilla1 stop$390
Puerto Plata
Puerto Plata1 stop$542
St. John's
St. John's1 stop$624
Punta Cana
Punta Cana1 stop$322
Santo Domingo
Santo Domingo1 stop$321
Montego Bay
Montego Bay1 stop$306
Oranjestad
Oranjestad1 stop$346
Nassau
Nassaunonstop$300
Kingston
Kingston1 stop$381
Simpson Bay
Simpson Bay1 stop$341
Providenciales
Providenciales1 stop$559
Port of Spain
Port of Spain1 stop$529
Bridgetown
Bridgetown1 stop$448
George Town
George Townnonstop$327
Willemstad
Willemstad1 stop$520
Castries
Castries2 stops$1,028
Aguadilla
Aguadilla1 stop$390
Puerto Plata
Puerto Plata1 stop$542
St. John's
St. John's1 stop$624

Book Cheap Tampa to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tampa to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Tampa to Caribbean Islands

Mon, May 18 - Wed, May 20
Multiple Airlines Logo
8:55 pm - 11:57 pm
TPA
-
SJU
3h 02mnonstop
Multiple Airlines Logo
7:30 am - 7:30 am
SJU
-
TPA
24h 00m
2 stops
$191Multiple Airlines
Sun, Jun 21 - Thu, Jun 25
Frontier Logo
9:35 pm - 12:37 am
TPA
-
SJU
3h 02mnonstop
Frontier Logo
5:15 pm - 8:30 pm
SJU
-
TPA
3h 15mnonstop
$192Frontier
Tue, Jun 23 - Wed, Jun 24
Frontier Logo
9:35 pm - 12:37 am
TPA
-
SJU
3h 02mnonstop
Frontier Logo
5:15 pm - 8:30 pm
SJU
-
TPA
3h 15mnonstop
$194Frontier
Fri, May 15 - Wed, May 20
American Airlines Logo
7:45 pm - 11:35 am
TPA
-
STT
15h 50m
1 stop
American Airlines Logo
5:05 pm - 9:20 am
STT
-
TPA
16h 15m
1 stop
$265American Airlines
Wed, Aug 19 - Wed, Aug 26
JetBlue Logo
11:05 am - 3:32 pm
TPA
-
STT
4h 27m
1 stop
JetBlue Logo
4:27 pm - 11:59 pm
STT
-
TPA
7h 32m
1 stop
$313JetBlue
Sat, Jun 13 - Tue, Jun 16
American Airlines Logo
6:00 am - 1:50 pm
TPA
-
NAS
7h 50m
1 stop
American Airlines Logo
8:00 am - 1:13 pm
NAS
-
TPA
5h 13m
1 stop
$314American Airlines
Mon, Aug 24 - Sun, Aug 30
JetBlue Logo
11:05 am - 3:32 pm
TPA
-
STT
4h 27m
1 stop
JetBlue Logo
4:27 pm - 11:28 pm
STT
-
TPA
7h 01m
1 stop
$318JetBlue
Mon, May 18 - Fri, May 22
Spirit Airlines Logo
8:25 am - 2:36 pm
TPA
-
AUA
6h 11m
1 stop
Spirit Airlines Logo
3:41 pm - 8:51 pm
AUA
-
TPA
5h 10m
1 stop
$346Spirit Airlines
Thu, Jun 25 - Sat, Jul 4
Spirit Airlines Logo
10:28 pm - 1:27 pm
TPA
-
STT
14h 59m
1 stop
Spirit Airlines Logo
2:32 pm - 9:33 pm
STT
-
TPA
7h 01m
1 stop
$346Spirit Airlines
Sat, Aug 22 - Thu, Aug 27
Copa Airlines Logo
5:21 am - 9:58 pm
TPA
-
AUA
16h 37m
1 stop
Copa Airlines Logo
7:10 am - 11:05 pm
AUA
-
TPA
15h 55m
1 stop
$393Copa Airlines
Booking Insights

KAYAK's insights & trends for Tampa to Caribbean Islands flights

Get data-powered insights and trends into flights from Tampa to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest Tampa to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from Tampa found in the last 72 hours was to Santo Domingo, at $143 round-trip. The most popular route is from Tampa (TPA) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $192.

What is the cheapest time of day to fly to Caribbean Islands?

The average price for all round-trip flights from Tampa to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $277 on average. Morning departures are around 2% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $366.

Can I save money by flying with a layover from Tampa to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $384, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Tampa to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tampa to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Tampa to Caribbean Islands is August, when tickets cost $95 (return) on average. On the other hand, the most expensive months are April and December, when the average cost of round-trip tickets is $1,064 and $933 respectively.

What’s the cheapest day of the week to fly from Tampa to Caribbean Islands?

The average price of all round-trip flights from Tampa to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For Tampa to Caribbean Islands, Sunday is the cheapest day to fly on average and Tuesday is the most expensive. Flying from Caribbean Islands back to Tampa, the best deals are generally found on Thursday, with Sunday being the most expensive.

How far in advance should I book a flight from Tampa to Caribbean Islands?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Tampa to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Tampa to Caribbean Islands, you should book around 2 weeks before departure, which saves you about 7% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 9 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$96
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from Tampa to San Juan Airport

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Tampa to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tampa to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tampa to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Tampa to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tampa to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Tampa to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tampa to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Tampa to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding cheap flights to Caribbean Islands

  • Looking for a cheap flight? 25% of our users found tickets from Tampa to the following destinations at these prices or less: San Juan $124 one-way - $265 round-trip

Reviews of the top 5 airlines serving from Tampa to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Tampa to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Tampa to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
9.0
Cayman AirwaysOverall score based on 33 reviews
7.2Entertainment
9.5Crew
6.3Food
9.0Boarding
8.6Comfort
Airline reviews

Flight departed early and arrived early. Excellent, orderly boarding, ample legroom. Great crew and a very smooth flight.

10.0 ExcellentJeffrey, Apr 2026
GCM - MIA
Read more Cayman Airways reviews

Flight departed early and arrived early. Excellent, orderly boarding, ample legroom. Great crew and a very smooth flight.

There is no food or entertainment in this flight. Service was excellent.

Short flight. Excellent boarding and crew. Flight left early and arrived early!

Great flight on the Twin Otter. Early departure and early arrival. Hassle free flight.

Boarded 20 minutes late, dinner and beverages were provided but the "main" of dinner was freezing cold and had soggy lettuce. The seats were wildly uncomfortable! There was in-flight entertainment that you can access via your phone (vs. the TV on the seatback in front of you) but the wifi connection was weak and you could not actually play anything. With that said, the crew was very pleasant and friendly!

Flight crew made the flight very enjoyable as they were friendly, helpful and accommodating. Flight time was 3:40 compared to the 4:30 that was captured on our itinerary, so that was a pleasant surprise. In flight entertainment was good with plenty of selection, however some of the choices that my family tried were slow to load and stalled out a few times. We were able to restart and everyone finished watching their movies. Food was pretty basic: croissant, turkey or chicken lunch meat with Swiss cheese and a bag of Lay’s potato chips. Still a bonus considering most airlines offerings which is nothing but peanuts or a cookie.

Best experience ever. Crew were amazing, kept me informed throughout. Boarding was on time and spot on. Id book again most def

Food could have been better, and internet that allows texting/WhatsApp and other basics on the phone instead of just inflight entertainment would have been nice.

My experience with JetBlue was fine BUT I am very upset with Kayak! JetBlue had delayed our scheduled departure by an hour and you NEVER notified me of the change. I did not hear directly from JetBlue because the trip was booked through Kayak, a mistake I will not repeat. Your reminder of the our trip last week still had the WRONG departure time. Our return trip has also changed, and again no notice from you.

Not having an assigned seat until boarding and then having to check my bag.

I purchased ticket so our daughter ( a minor) can sit next to her mother. No help at gate after kayak insisted that this could be done. She ended sitting by herself

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

For a 4 1/2 hour international flight all we got was 1 small pack of cookies and a drink. You had to watch movies on your own devise.

The seats need better cushioning for a nearly 5-hour flight, it was a bit uncomfortable. I'm glad American has free wi-fi but there were was a bout 30 minutes in the middle of the flight when there was no connection which was frustrating.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Flight: Started on time. Comfortable flight. Arrived on time. Crew: Very cordial and helpful. Drinks and snack was served with a smile. Overall enjoyed the trip. Regards, Hari Doss Chanchala Doss

I’m sure Business Class would be excellent. I feel like I got what I paid for. Overall it was good and well worth it. I would do it again.

This short sector between Miami and JFK was undertaken purely for business purposes, with efficiency as the primary objective rather than a full inflight experience. Overall, the journey met its intended purpose; however, the ground experience at Miami stood out significantly. During check-in, I was unable to link my frequent flyer details from Qatar Airways (oneworld alliance) through either the self-service kiosk or web check-in. The situation was handled exceptionally well by the check-in agent, who demonstrated remarkable ownership. She coordinated across multiple counters, ensured my frequent flyer number was correctly reflected, reissued the boarding pass, and confirmed that mileage accrual would be recognized. Additionally, she ensured the boarding pass reflected priority status, enabling a seamless priority check-in experience without delays. This level of proactive service was both commendable and impactful. Boarding and the inflight experience, operated by American Airlines under a codeshare arrangement, were efficient but largely transactional. While operational delivery was smooth, there was no visible recognition of oneworld frequent flyer status onboard. In comparison to the consistently personalized engagement typically experienced with Qatar Airways, this absence was noticeable—though understandably a potential limitation of codeshare alignment rather than a direct service shortfall. In summary, while the flight itself fulfilled its operational intent, the exceptional professionalism and commitment demonstrated at the Miami check-in counter was the defining highlight of this journey. Greater consistency in elite recognition across partner airlines would further enhance the overall experience.

Business class was very good, one of my best flights

Incredibly delayed. First delay was due to plane coming in being late. Resulted in 30 minute delay. Boarded and then had multiple mechanical issues. Was on plane for an hour until they told people they could get off if they wanted but couldn't come back. Then gate agent rushed in and said they had lost control of who went off and we would all have to deplane and then get back on. They said flight had not been cancelled. Then while sitting waiting to board again they announced it would take two hours to get new plane and to wait at new gate. New plane arrived, reboarded only to find out that pilots had timed out. Waited for new pilots. In that time one of the flight attendants timed out. Never received food or water while waiting. Was confusing mess as to what was happening. Even flight attendants and gate agents were getting frustrated. Almost 6 hours delayed. Called American to received flight credit but can't get anywhere as Kayak reservation and don't have a ticket number. Reached out to Kayak but never heard back.

The new planes (American Eagle) are beautiful and especially comfortable. The flight attendants are consistently professional and courteous. And, while it may seem inconsequential, the new liquid tube of coffee creamer—in contrast to the powdered coffee creamer—makes all the difference in a cup of coffee.

Flight was delayed and they gave up my seat on my connection, even when I could still make the flight

There was a crack in my window seal. And Spirit is now closed forever.

They closed the doors earlier than posted. I missed my flight with a slim 5 minutes bc they closed the doors earlier than earlier. My luggage never made it onto the flight and I had to find a new flight to Dallas bc the only option they could rebook me on was for leaving miami.

The AC broke and we were onboard for 2 hrs waiting for them to fix it. It was so hot and we could not get any water or anything to drink. They finally let us off the plane after the second attempt and we boarded a new plane. We didn't land till 12:15am!

There was no flight. Call the airline and confirmed. I have no idea why you think that I flew on the days that you say I did.

Easy to get our TSA pre check #added. Flight crew was great and entertaining and we landed early!

baggage drop off was a bit much. I felt like I worked for spirit airlines since I did all the work.

Gate changed multiple times. The staff seemed annoyed that we asked for water. We had to pay for the water as well.

We didn't get on the flight, they canceled our flight and said there was no flights leaving this weekend and sent me our money back.

Horrible company: canceled flights and delayed flights. Spirit canceled my flight from Miami to Philadelphia the day before we were supposed to leave from Philadelphia to Miami, with no explanation. I had to rebook another flight, spending more money and instead of flying from Miami, I had to choose a flight from Fort Lauderdale because there were no direct flights available from Miami. That created additional cost. The flight with Spirit from Fort Lauderdale was scheduled to depart at 6am, so I had to wake up my 3 and 6 years old at 3am to get to the airport in time and then, at 5am while we were at the gate the delayed the flight until 7:45am with again no explanation.

The flight was delayed four times and finally cancelled. The hotel night we paid for and the connecting flight did not happen. There were also additional costs due to the extra night in Miami. I do not recommend this airline.

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

Plane was hot and miserable and the crew was rude!

12 hour delay required getting on and off plane 3 times - would have at least liked to have been offered a snack or drink

It was an early flight and most people napped/slept and the crew let us which was nice.

It didn’t happen. I booked it and then was told it wasn’t available and then forced to pay far higher prices for a worse option

This company socks. It's fraud. They canceled our flight yesterday, and today we were late because of a really long line at the check in bag. At the rebook station, there was ton of people. The workers were all rude. I am gonna make a report to FTC.

Flight got delayed for 5 hours no good explanation was offered ;(

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports