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Flight Deals
Cheap Flights from Gainesville to Caribbean
Cheapest round-trip prices found by our users on KAYAK in the last 5 daysBook 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
Sat, Jan 23 - Tue, Feb 2
2:44 pm - 12:24 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
20h 40m2 stops Charlotte Douglas Miami
3:00 pm - 11:22 pmSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
9h 22m1 stop Miami
$478American Airlines
Tue, Jan 26 - Tue, Feb 2
6:00 am - 1:18 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
6h 18m1 stop Charlotte Douglas
1:14 pm - 10:20 amSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
22h 06m2 stops Miami Charlotte Douglas
$478American Airlines
Tue, Jan 26 - Wed, Feb 3
7:40 am - 4:14 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
7h 34m1 stop Miami
4:21 pm - 11:17 pmSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
7h 56m1 stop Charlotte Douglas
$478American Airlines
Tue, Jan 26 - Tue, Feb 2
6:38 pm - 12:24 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
16h 46m2 stops Charlotte Douglas Miami
1:14 pm - 10:20 amSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
22h 06m2 stops Miami Charlotte Douglas
$478American Airlines
Sat, Jan 23 - Tue, Feb 2
5:09 pm - 12:24 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
18h 15m2 stops Dallas/Fort Worth Miami
5:04 pm - 10:20 amSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
18h 16m2 stops Miami Charlotte Douglas
$478American Airlines
Mon, Jan 25 - Tue, Feb 2
6:00 am - 1:18 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
6h 18m1 stop Charlotte Douglas
1:14 pm - 11:22 pmSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
11h 08m1 stop Miami
$478American Airlines
Mon, Jan 25 - Tue, Feb 2
6:20 am - 12:24 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
5h 04m1 stop Miami
1:14 pm - 10:20 amSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
22h 06m2 stops Miami Charlotte Douglas
$478American Airlines
Sun, Jan 24 - Tue, Feb 2
2:44 pm - 12:24 pmGNV Gainesville Regional-STT Saint Thomas Island Cyril E King
20h 40m2 stops Charlotte Douglas Miami
5:04 pm - 10:20 amSTT Saint Thomas Island Cyril E King-GNV Gainesville Regional
18h 16m2 stops Miami Charlotte Douglas
$478American Airlines
Tue, Jan 19 - Wed, Jan 27
3:26 pm - 11:58 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
7h 32m1 stop Atlanta Hartsfield-Jackson
4:10 pm - 10:46 pmSJU San Juan Luis Munoz Marin Intl-GNV Gainesville Regional
7h 36m1 stop Atlanta Hartsfield-Jackson
$538Delta
Wed, Jan 20 - Sun, Jan 24
6:00 am - 12:49 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
5h 49m1 stop Atlanta Hartsfield-Jackson
6:30 am - 2:40 pmSJU San Juan Luis Munoz Marin Intl-GNV Gainesville Regional
9h 10m1 stop Atlanta Hartsfield-Jackson
$578Delta
Recent one-way flight deals from Gainesville to Caribbean
Fri, Jan 1
10:10 am - 9:13 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
10h 03m1 stop Atlanta Hartsfield-Jackson
$334Delta
Fri, Jan 1
10:10 am - 9:13 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
10h 03m1 stop Atlanta Hartsfield-Jackson
$334Delta
Fri, Jan 1
7:32 pm - 9:36 amGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
13h 04m2 stops Charlotte Douglas Miami
$347American Airlines
Fri, Jan 1
7:32 pm - 10:51 amGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
14h 19m2 stops Charlotte Douglas Miami
$347American Airlines
Fri, Nov 13
10:16 am - 5:43 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
6h 27m1 stop Atlanta Hartsfield-Jackson
$454Delta
Tue, Nov 10
3:53 pm - 11:15 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
6h 22m1 stop Atlanta Hartsfield-Jackson
$498Delta
Mon, Nov 9
3:53 pm - 11:15 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
6h 22m1 stop Atlanta Hartsfield-Jackson
$498Delta
Wed, Nov 11
3:53 pm - 11:15 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
6h 22m1 stop Atlanta Hartsfield-Jackson
$498Delta
Sat, Nov 7
1:33 pm - 11:18 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
8h 45m1 stop Atlanta Hartsfield-Jackson
$524Delta
Thu, Nov 12
1:31 pm - 11:15 pmGNV Gainesville Regional-SJU San Juan Luis Munoz Marin Intl
8h 44m1 stop Atlanta Hartsfield-Jackson
$524Delta
Recent last minute flight deals from Gainesville to Caribbean
Fri, Nov 6 - Sun, Nov 8
5:55 pm - 3:37 pmGNV Gainesville Regional-POS Port of Spain Piarco Intl
20h 42m2 stops Charlotte Douglas Miami
4:42 pm - 11:59 pmPOS Port of Spain Piarco Intl-GNV Gainesville Regional
8h 17m1 stop Miami
$947American Airlines
Fri, Nov 6 - Sun, Nov 8
5:55 pm - 3:37 pmGNV Gainesville Regional-POS Port of Spain Piarco Intl
20h 42m2 stops Charlotte Douglas Miami
4:42 pm - 6:06 pmPOS Port of Spain Piarco Intl-GNV Gainesville Regional
26h 24m2 stops Miami Charlotte Douglas
$947American Airlines
Fri, Nov 6 - Sun, Nov 8
6:00 am - 3:37 pmGNV Gainesville Regional-POS Port of Spain Piarco Intl
8h 37m1 stop Miami
4:42 pm - 11:59 pmPOS Port of Spain Piarco Intl-GNV Gainesville Regional
8h 17m1 stop Miami
$1,259American Airlines
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.
Prices
Airlines
More
Good to know
Low season | June |
|---|---|
High season | January |
Cheapest flight | $334 |
FAQs - booking Caribbean flights
Reviews of the top airline flying from Gainesville to Caribbean
7.0
American AirlinesOverall score based on 12215 reviews
7.4Boarding
6.4Food
7.9Crew
6.8Entertainment
7.2Comfort
Airline reviews
Seats were very tight for a 17 hour flight. Baby cried for 15 out of 17 hours.
4.0 OkayBarbara, Oct 2026
Seats were very tight for a 17 hour flight. Baby cried for 15 out of 17 hours.
Good flight, excellent personnel; poor comfort, small seats, big cost.
This trip on American was the WORST I have ever experienced. The plan was LATE taking off from Tucson due to mechanical issues. It caused me to arrive late in Dallas, so I tried to move flights so I would not miss my dinner meeting. First attempt, that flight was delayed, Second attempt, that flight was also delayed. Got back on original flight, the mechanical issue was NOT fixed, so we de-planed and had to find the new gate. Overall, was which was 4 hours delayed and missed the dinner meeting. Friday return, flight from Orlando was on time and landed early. Then the next flight was delayed due to crew coming in late, and them waiting on other passengers. After 90 minutes of delay, we boarded, and then were informed the Fist Officer could not fly due to time constraints. At 12:15 AM we were offered a hotel for a 4:20 boarding flight. Not happening. DFW was COLD and no place to sleep. Plane delayed again to 6:50, but was late taking off AGAIN. Finally landed in Tucson at around 8AM. Should be refunded 75% of the ticket costs due to negligence, nothing more.
Cabin was bone dry, no humidity whatsoever, and pretty warm; and beverage service didn't start for at least an hour. I had to go to the back for water and the FAs tried telling me it was always this way for all Miami flights, which is complete nonsense. Avoid the MAX8 like the plague.
Im sitting here waiting over an hour for my golf clubs
Flight was 2+ hours delayed and they “misplaced” all 3 of our checked-in bags.
Quick flight. No time to stress over it. Over before it begins.
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
why would I bother with this airline and pick seats when I am asked to move for a weight imbalance
I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.
More options for your flight to Caribbean
Complete your trip to Caribbean with a hotel stay or car rental
Information on your arrival and departure airports
Cabin class types available on flights to Gainesville
Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights from domestic origins to Gainesville
Flights from all regions of Gainesville to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to other popular destinations
The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
Flights to popular destinations in Caribbean
Flights to Antigua And Barbudafrom $1,058
Flights to Arubafrom $3,900
Flights to Barbadosfrom $766
Flights to Cubafrom $854
Flights to Curaçaofrom $1,152
Flights to Dominican Republicfrom $751
Flights to Haitifrom $760
Flights to Jamaicafrom $924
Flights to Puerto Ricofrom $538
Flights to St. Maartenfrom $1,317
Flights to The Bahamasfrom $518
Flights to Turks and Caicos Islandsfrom $797
Flights to U.S. Virgin Islandsfrom $478