$253 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 5/2. 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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 24% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

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$601
Montego Bay
Montego Bay1 stop$701
Nassau
Nassau1 stop$536
Kingston
Kingston1 stop$814
Simpson Bay
Simpson Bay1 stop$642
St. John's
St. John's1 stop$792
Punta Cana
Punta Cana1 stop$601
Montego Bay
Montego Bay1 stop$701
Nassau
Nassau1 stop$536
Kingston
Kingston1 stop$814
Simpson Bay
Simpson Bay1 stop$642
St. John's
St. John's1 stop$792

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

Mo, Aug 3 - Fr, Aug 7
Delta Logo
1:08 pm - 10:29 pm
GNV
-
SJU
9h 21m
1 stop
Delta Logo
6:00 am - 2:56 pm
SJU
-
GNV
8h 56m
1 stop
$436Delta
So, Aug 9 - Do, Aug 13
American Airlines Logo
7:34 pm - 12:48 pm
GNV
-
SJU
17h 14m
2 stops
American Airlines Logo
4:53 pm - 10:14 am
SJU
-
GNV
17h 21m
2 stops
$441American Airlines
Di, Aug 18 - Sa, Aug 22
American Airlines Logo
6:39 pm - 9:43 am
GNV
-
SJU
15h 04m
2 stops
American Airlines Logo
1:38 pm - 11:59 pm
SJU
-
GNV
10h 21m
1 stop
$471American Airlines
Sa, Jun 13 - Di, Jun 16
American Airlines Logo
7:32 pm - 9:39 am
GNV
-
SJU
14h 07m
2 stops
American Airlines Logo
11:55 am - 11:59 pm
SJU
-
GNV
12h 04m
1 stop
$481American Airlines
Mi, Aug 5 - Mo, Aug 10
American Airlines Logo
6:39 pm - 12:48 pm
GNV
-
SJU
18h 09m
2 stops
American Airlines Logo
7:14 pm - 11:59 pm
SJU
-
GNV
4h 45m
1 stop
$486American Airlines
Di, Mai 19 - Di, Mai 26
Delta Logo
1:11 pm - 10:17 pm
GNV
-
SJU
9h 06m
1 stop
Delta Logo
6:15 am - 12:22 pm
SJU
-
GNV
6h 07m
1 stop
$490Delta
Di, Mai 19 - Di, Mai 26
American Airlines Logo
6:49 pm - 10:53 am
GNV
-
SJU
16h 04m
2 stops
American Airlines Logo
11:55 am - 11:59 pm
SJU
-
GNV
12h 04m
1 stop
$501American Airlines
Do, Aug 13 - Mo, Aug 17
WestJet Logo
10:20 am - 11:45 am
GNV
-
MBJ
26h 25m
2 stops
WestJet Logo
12:45 pm - 4:06 pm
MBJ
-
GNV
26h 21m
2 stops
$1,635WestJet
Mi, Jun 24 - Mi, Jul 1
WestJet Logo
10:17 am - 11:45 am
GNV
-
MBJ
26h 28m
2 stops
WestJet Logo
12:45 pm - 4:32 pm
MBJ
-
GNV
26h 47m
2 stops
$1,645WestJet
Mi, Aug 26 - Mi, Sep 2
WestJet Logo
7:05 pm - 11:45 am
GNV
-
MBJ
41h 40m
2 stops
WestJet Logo
12:45 pm - 12:22 pm
MBJ
-
GNV
22h 37m
2 stops
$1,696WestJet
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.

Which airlines provide the cheapest flights from Gainesville to Caribbean?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Gainesville to Caribbean were found on Delta ($436) and American Airlines ($441).

Good to know

Low seasonFebruary
Cheapest flight$253
Best time to beat the crowds with an average 34% drop in price.
Most popular time to fly and prices are also 20% 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 11645 reviews
7.9Crew
6.9Entertainment
6.4Food
7.2Comfort
7.5Boarding
Airline reviews

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.

8.0 ExcellentJoseph, Apr 2026
TPA - PHX
Read more American Airlines reviews

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

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports