$313 Find Cheap Flights from Gainesville to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Gainesville to Caribbean departing on 11/15. 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

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Cheap Flights from Gainesville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$608
Montego Bay
Montego Bay2 stops$2,555
Nassau
Nassau2 stops$1,653
Kingston
Kingston1 stop$685
Simpson Bay
Simpson Bay2 stops$3,667
St. John's
St. John's1 stop$696
Punta Cana
Punta Cana1 stop$608
Montego Bay
Montego Bay2 stops$2,555
Nassau
Nassau2 stops$1,653
Kingston
Kingston1 stop$685
Simpson Bay
Simpson Bay2 stops$3,667
St. John's
St. John's1 stop$696

Book Cheap Gainesville to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Gainesville to Caribbean 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 Gainesville to Caribbean

Tue, Aug 4 - Tue, Aug 11
Delta Logo
6:00 am - 11:46 am
GNV
-
SJU
5h 46m
1 stop
Delta Logo
7:00 am - 2:55 pm
SJU
-
GNV
7h 55m
1 stop
$446Delta
Fri, Sep 4 - Mon, Sep 7
American Airlines Logo
6:15 am - 9:55 pm
GNV
-
SJU
15h 40m
1 stop
American Airlines Logo
7:30 am - 6:08 pm
SJU
-
GNV
10h 38m
1 stop
$536American Airlines
Mon, Jun 29 - Mon, Jul 6
American Airlines Logo
7:32 pm - 11:02 am
GNV
-
SJU
15h 30m
2 stops
American Airlines Logo
11:54 am - 11:59 pm
SJU
-
GNV
12h 05m
1 stop
$556American Airlines
Sat, Jun 27 - Sat, Jul 4
American Airlines Logo
7:32 pm - 11:02 am
GNV
-
SJU
15h 30m
2 stops
American Airlines Logo
7:25 am - 6:56 pm
SJU
-
GNV
11h 31m
1 stop
$591American Airlines
Mon, Jun 15 - Thu, Jun 18
American Airlines Logo
7:32 pm - 9:39 am
GNV
-
SJU
14h 07m
2 stops
American Airlines Logo
2:56 pm - 11:59 pm
SJU
-
GNV
9h 03m
1 stop
$606American Airlines
Wed, Jul 15 - Wed, Jul 22
American Airlines Logo
6:00 am - 3:18 pm
GNV
-
PUJ
9h 18m
1 stop
American Airlines Logo
12:03 pm - 11:59 pm
PUJ
-
GNV
11h 56m
1 stop
$608American Airlines
Fri, Sep 4 - Tue, Sep 8
Delta Logo
1:08 pm - 8:13 pm
GNV
-
KIN
8h 05m
1 stop
Delta Logo
9:00 am - 10:30 pm
KIN
-
GNV
12h 30m
1 stop
$714Delta
Sun, Nov 8 - Wed, Nov 11
WestJet Logo
3:45 pm - 3:40 pm
GNV
-
NAS
23h 55m
2 stops
WestJet Logo
4:50 pm - 10:27 pm
NAS
-
GNV
29h 37m
2 stops
$1,653WestJet
Fri, Jun 19 - Mon, Jun 22
WestJet Logo
7:04 pm - 11:45 am
GNV
-
MBJ
41h 41m
2 stops
WestJet Logo
12:45 pm - 12:25 pm
MBJ
-
GNV
22h 40m
2 stops
$2,555WestJet
Sun, Aug 23 - Thu, Aug 27
WestJet Logo
6:00 am - 2:20 pm
GNV
-
SXM
32h 20m
2 stops
WestJet Logo
3:10 pm - 10:48 pm
SXM
-
GNV
31h 38m
2 stops
$3,667WestJet
Booking Insights

KAYAK's insights & trends for Gainesville to Caribbean flights

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

What is the cheapest month to fly from Gainesville to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Gainesville to Caribbean, 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 Gainesville to Caribbean is September, when tickets cost $0 (return) on average. On the other hand, the most expensive months are May and March, when the average cost of round-trip tickets is $1,279 and $1,060 respectively.

Good to know

Low seasonJune
Cheapest flight$313
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 17% lower on average.
Flight from Gainesville to Saint Thomas Island

FAQs - booking Caribbean flights

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

    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 Gainesville to Caribbean.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Gainesville to Caribbean 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 Gainesville to Caribbean?

    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 Gainesville to Caribbean 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 Gainesville to Caribbean?

    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 Gainesville to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Gainesville to Caribbean

 
Need help choosing which airline to fly with from Gainesville to Caribbean? 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.
7.1
American AirlinesOverall score based on 11641 reviews
7.5Boarding
7.9Crew
6.4Food
6.9Entertainment
7.2Comfort
Airline reviews

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

10.0 ExcellentJolene, May 2026
GNV - DFW
Read more American Airlines reviews

It was what i expected. I like the movies you can access from your phone. It would be nice if there was a gluten free snack offered. But I did bring my own snack knowing there would not be a gluten free option

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Requested early boarding to disinfect seat, tray table, etc. before general boarding. Instructed to board after wheelchair passengers. Waited on jet bridge behind 12 wheelchair passengers. Stopped immediately after entering plane to wait for gate agent in rear of plane cleaning a seat that was wet, got to my row and found both seats adjacent to mine already occupied, with the lack of room making it impossible for me to clean my own space and defeating the purpose of my boarding early. Cleaned the armrests and tray table as best I could.

We had several flights and they were all on-time and flawless

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports