$165 Find Cheap Flights from Orlando Sanford Intl 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 Orlando Sanford Intl to Caribbean Islands departing on 3/2. 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 Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Orlando to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Book Cheap Orlando Sanford Intl 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 Orlando Sanford Intl 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 Orlando Sanford Intl to Caribbean Islands

Fri, Mar 6 - Tue, Mar 17
Multiple Airlines Logo
4:40 pm - 3:11 pm
SFB
-
SJU
21h 31m
1 stop
Multiple Airlines Logo
7:54 pm - 12:36 pm
SJU
-
SFB
40h 42m
2 stops
$380Multiple Airlines
Fri, Mar 20 - Wed, Mar 25
Multiple Airlines Logo
5:40 pm - 1:42 pm
SFB
-
SJU
20h 02m
1 stop
Multiple Airlines Logo
12:55 pm - 1:41 pm
SJU
-
SFB
24h 46m
2 stops
$388Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
4:40 pm - 3:11 pm
SFB
-
SJU
21h 31m
1 stop
Multiple Airlines Logo
3:36 pm - 12:53 pm
SJU
-
SFB
21h 17m
2 stops
$390Multiple Airlines
Fri, Mar 6 - Mon, Mar 9
Multiple Airlines Logo
4:40 pm - 3:11 pm
SFB
-
SJU
21h 31m
1 stop
Multiple Airlines Logo
1:51 pm - 1:45 pm
SJU
-
SFB
23h 54m
1 stop
$392Multiple Airlines
Fri, Feb 20 - Mon, Feb 23
Multiple Airlines Logo
3:48 pm - 2:22 pm
SFB
-
SJU
21h 34m
2 stops
Multiple Airlines Logo
1:49 pm - 12:45 pm
SJU
-
SFB
23h 56m
1 stop
$432Multiple Airlines
Thu, Mar 5 - Mon, Mar 9
Multiple Airlines Logo
8:10 am - 12:41 am
SFB
-
SJU
15h 31m
2 stops
Multiple Airlines Logo
1:51 pm - 1:45 pm
SJU
-
SFB
23h 54m
1 stop
$449Multiple Airlines
Thu, Feb 12 - Mon, Feb 16
Multiple Airlines Logo
2:16 pm - 2:25 am
SFB
-
SJU
35h 09m
2 stops
Multiple Airlines Logo
1:49 pm - 12:45 pm
SJU
-
SFB
23h 56m
1 stop
$483Multiple Airlines
Tue, Apr 14 - Fri, Apr 17
Multiple Airlines Logo
1:55 pm - 9:45 pm
SFB
-
SJU
7h 50m
1 stop
Multiple Airlines Logo
11:00 am - 4:10 pm
SJU
-
SFB
5h 10m
1 stop
$520Multiple Airlines
Sun, Mar 15 - Sat, Mar 21
Multiple Airlines Logo
4:05 pm - 5:16 pm
SFB
-
SJU
25h 11m
1 stop
Multiple Airlines Logo
3:12 pm - 12:36 pm
SJU
-
SFB
21h 24m
2 stops
$617Multiple Airlines
Sun, Feb 15 - Wed, Feb 18
Multiple Airlines Logo
3:05 pm - 5:19 pm
SFB
-
SJU
25h 14m
1 stop
Multiple Airlines Logo
4:31 pm - 8:46 pm
SJU
-
SFB
29h 15m
2 stops
$626Multiple Airlines
Booking Insights

KAYAK's insights & trends for Orlando Sanford Intl to Caribbean Islands flights

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

What is the cheapest Orlando Sanford Intl Airport 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 Orlando Sanford Intl Airport found in the last 72 hours was to Punta Cana, at $205 round-trip. The most popular route is from Orlando Sanford Intl Airport (SFB) to Punta Cana (PUJ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $205.

Can I save money by flying with a layover from Orlando Sanford Intl Airport 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 $202, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Orlando Sanford Intl Airport to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Orlando Sanford Intl Airport 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 Orlando Sanford Intl Airport to Caribbean Islands is April, when tickets cost $108 (return) on average. On the other hand, the most expensive months are August and September, when the average cost of round-trip tickets is $310 and $300 respectively.

Good to know

Low seasonOctober
Cheapest flight$165
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly and prices are also 21% lower on average.
Flight from Orlando Sanford Intl to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Orlando Sanford Intl 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 Orlando Sanford Intl to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Orlando Sanford Intl 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 Orlando Sanford Intl 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 Orlando Sanford Intl 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 Orlando Sanford Intl 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 Orlando Sanford Intl 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 Orlando Sanford Intl to the following destinations at these prices or less: Punta Cana $126 one-way - $216 round-trip

Reviews of the top airlines flying from Orlando Sanford Intl to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Orlando 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 Orlando Sanford Intl 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.
6.6
ArajetOverall score based on 43 reviews
6.7Boarding
4.6Entertainment
5.3Food
7.4Crew
6.4Comfort
Airline reviews

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

2.0 MediocreAnonymous, Dec 2025
SDQ - EZE
Read more Arajet reviews

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

The ticket you issued was an hour after when the real flight was

I didn’t get a chance to experience anything because the 3rd party company that receives payment did a really bad job. After I received confirmation number I went to bed then I tried to check in my confirmation number did not work then I received a massage that my payment did not go through I called the company to rectify the problem and I was told that confirmation the whole thing was cancelled and that they couldn’t do anything about it and hang up the phone. So I decided to purchase a new ticket from another airline. I will never use kayak again and I’ll make sure all the people in my circle doesn’t deal with you guys.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports