$274 Find Cheap Flights from Gainesville to Caribbean - Compare and Save

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 5 days
Sort by: Cheapest
Saint Thomas Island, U.S. Virgin Islands
5h 22m2 stops
from $473per person
San Juan, Puerto Rico
5h 31m2 stops
from $498per person
Montego Bay, Jamaica
4h 15m2 stops
from $570per person
Puerto Plata, Dominican Republic
Puerto Plata, Dominican Republic
6h 05m2 stops
from $667per person
Willemstad, Curaçao
Willemstad, Curaçao
6h 10m2 stops
from $669per person
Simpson Bay, St. Maarten
Simpson Bay, St. Maarten
5h 14m2 stops
from $695per person
Port of Spain, Trinidad and Tobago
Port of Spain, Trinidad and Tobago
7h 07m2 stops
from $718per person
Oranjestad, Aruba
Oranjestad, Aruba
9h 50m2 stops
from $751per person
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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?

The cheapest month for flights from Gainesville to Caribbean is November, when tickets cost $0 (return) on average. On the other hand, the most expensive months are May and July, when the average cost of round-trip tickets is $1,279 and $780 respectively.

Good to know

Low season

June

Cheapest flight

$274
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly and prices are also 18% lower on average.
Flight from Gainesville to San Juan

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.
7.0
American AirlinesOverall score based on 12130 reviews
6.8Entertainment
7.9Crew
6.4Food
7.4Boarding
7.2Comfort
Airline reviews

My boarding pass said gate E5. I arrived at gate E5 by 12:45pm. At 2:10pm, I received a phone call stating I was supposed to be at gate D37. They would not wait for me to get there (by the way, the plane was still there when I got to gate D37, but everything was closed and no one was at the door). The next flight at 7:40pm was sold out; was told I'd be put on the 9:47pm flight. I was so stressed, I became chokey (apparently I have mild asthma). By the grace of God, a lot of begging, and the customer service rep taking pity on me, I was able to get on a 4:50pm flight to Philadelphia.

2.0 MediocreMelissa, Oct 2026
Read more American Airlines reviews

My boarding pass said gate E5. I arrived at gate E5 by 12:45pm. At 2:10pm, I received a phone call stating I was supposed to be at gate D37. They would not wait for me to get there (by the way, the plane was still there when I got to gate D37, but everything was closed and no one was at the door). The next flight at 7:40pm was sold out; was told I'd be put on the 9:47pm flight. I was so stressed, I became chokey (apparently I have mild asthma). By the grace of God, a lot of begging, and the customer service rep taking pity on me, I was able to get on a 4:50pm flight to Philadelphia.

Comfy and timely flight thanks to Cathay to all crew and the captain for our smooth landing.. above all thank You Lord for our Safe flight ❤️🙌🙏🏽

I have executive platinum status with American Airlines. It seems impossible to be upgraded anymore and I’m never offered a cheese plate or thanked for my loyalty.

In premium economy I was expecting a bit cleaner area. Tables were not very clean. Only one of us received a blanket and pillow. The food was okay. Probably a smidgen better than coach. The crew were very nice but should have done more walk through to at least pick up trash.

We had a 1 hour delay due to mechanical issues, then another hour, then 2, and eventually it was an 8 hour delay. The airport staff was confused about gate changes, as they were not getting good communication. They were trying, but we changed gates 5 times in one hour!

Horrible. Flight was delayed for 4 hours first till 7pm. Then for one more hour. Then again and around 9pm we were finally boarded and waited for catering delivery for another hour. At 10pm we were not interested on food at all. Tired, sleepy we arrived after midnight. Insane.

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