$100 Find Cheap Flights from Pensacola to Florida Keys - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Pensacola to Florida Keys departing on 9/26. 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.
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Cheap Flights from Pensacola to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$200
Key West
Key West1 stop$215
Miami
Miami1 stop$200
Key West
Key West1 stop$215

Book Cheap Pensacola to Florida Keys Plane Tickets

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

Sat, Sep 19 - Sat, Sep 26
Frontier Logo
6:59 pm - 5:48 am
PNS
-
MIA
9h 49m
1 stop
Frontier Logo
7:20 am - 6:04 pm
MIA
-
PNS
11h 44m
1 stop
$200Frontier
Tue, Aug 25 - Tue, Sep 1
Frontier Logo
7:26 pm - 4:52 am
PNS
-
MIA
8h 26m
1 stop
Frontier Logo
6:00 am - 6:31 pm
MIA
-
PNS
13h 31m
1 stop
$200Frontier
Tue, Aug 25 - Tue, Sep 1
Frontier Logo
7:26 pm - 4:52 am
PNS
-
MIA
8h 26m
1 stop
Frontier Logo
6:00 am - 6:31 pm
MIA
-
PNS
13h 31m
1 stop
$200Frontier
Tue, Sep 8 - Tue, Sep 15
American Airlines Logo
6:05 am - 1:05 pm
PNS
-
EYW
6h 00m
1 stop
American Airlines Logo
6:27 pm - 10:10 pm
EYW
-
PNS
4h 43m
1 stop
$271American Airlines
Tue, Aug 25 - Tue, Sep 1
American Airlines Logo
6:05 am - 10:56 am
PNS
-
EYW
3h 51m
1 stop
American Airlines Logo
11:30 am - 4:27 pm
EYW
-
PNS
5h 57m
1 stop
$271American Airlines
Tue, Sep 8 - Sat, Sep 12
American Airlines Logo
6:30 am - 12:55 pm
PNS
-
EYW
5h 25m
1 stop
American Airlines Logo
6:31 pm - 10:10 pm
EYW
-
PNS
4h 39m
1 stop
$271American Airlines
Wed, Sep 9 - Wed, Sep 16
Delta Logo
6:00 am - 10:46 am
PNS
-
EYW
3h 46m
1 stop
Delta Logo
6:19 pm - 11:21 pm
EYW
-
PNS
6h 02m
1 stop
$295Delta
Tue, Nov 17 - Thu, Nov 26
Delta Logo
7:00 am - 1:01 pm
PNS
-
EYW
5h 01m
1 stop
Delta Logo
6:02 pm - 10:04 pm
EYW
-
PNS
5h 02m
1 stop
$295Delta
Mon, Nov 9 - Mon, Nov 9
Southwest Logo
7:45 am - 2:35 pm
PNS
-
MIA
5h 50m
1 stop
Southwest Logo
5:00 pm - 8:30 pm
MIA
-
PNS
4h 30m
1 stop
$331Southwest
Sat, Aug 29 - Tue, Sep 1
Southwest Logo
7:05 am - 1:55 pm
PNS
-
MIA
5h 50m
1 stop
Southwest Logo
9:15 am - 2:05 pm
MIA
-
PNS
5h 50m
1 stop
$331Southwest
Booking Insights

KAYAK's insights & trends for Pensacola to Florida Keys flights

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

What is the cheapest time of day to fly to Florida Keys?

The average price for all round-trip flights from Pensacola to Florida Keys depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $555 on average. Morning departures are around 1% cheaper than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the evening, which is peak travel time and where the average cost of a ticket is $597.

Can I save money by flying with a layover from Pensacola to Florida Keys?

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 $371, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Pensacola to Florida Keys?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Pensacola to Florida Keys, 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 Pensacola to Florida Keys is August, when tickets cost $332 (return) on average. On the other hand, the most expensive months are June and May, when the average cost of round-trip tickets is $505 and $502 respectively.

What’s the cheapest day of the week to fly from Pensacola to Florida Keys?

The average price of all round-trip flights from Pensacola to Florida Keys clicked on KAYAK for each day over the last 12 months.

For Pensacola to Florida Keys, Saturday is the cheapest day to fly on average and Monday is the most expensive. Flying from Florida Keys back to Pensacola, the best deals are generally found on Wednesday, with Sunday being the most expensive.

How far in advance should I book a flight from Pensacola to Florida Keys?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Pensacola to Florida Keys, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Pensacola to Florida Keys, you should book around 3 weeks before departure, which saves you about 32% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low season

March

Cheapest flight

$100
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from Pensacola to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Pensacola to Florida Keys?

    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 Pensacola to Florida Keys.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Pensacola to Florida Keys 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 Pensacola to Florida Keys?

    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 Pensacola to Florida Keys 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 Pensacola to Florida Keys?

    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 Pensacola to Florida Keys 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 Florida Keys

  • Looking for a cheap flight? 25% of our users found tickets from Pensacola to the following destinations at these prices or less: Miami $324 one-way - $495 round-trip

Reviews of the top 4 airlines serving from Pensacola to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Pensacola to Florida Keys. 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 Pensacola to Florida Keys? 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.
8.0
SouthwestOverall score based on 4227 reviews
7.0Food
8.1Boarding
7.5Entertainment
8.6Crew
8.0Comfort
Airline reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

6.0 GoodGordon, Jul 2026
SAN - MCO
Read more Southwest reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Easy to book and to get check in and get on and off.

We were skipped when the snack cart passed and then the attendant said we weren’t . I am disabled and was in a row toward the back of the plane which was very difficult for me to navigate. Disabled people should not be forced to walk the plank.

Flight was delayed and then "they did not have time to load food". No snack or drink at all for 1.5 how flight. Somebody wasn't prepared.

It is usually very pleasant. Good service for the price, international flights are even better

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

It’s was good. There’s so much room for improvement though. Since the plane was small, there was no entertainment but for years now, the most jarring aspect of travel is the lack of tasty snacks.

I liked the ease of checking in, luggage check in, wheel chair assistance, boarding and flight.

Quick flight. No time to stress over it. Over before it begins.

It was awful. My first flight was delayed and as a consequence I lost my second flight to Greensboro. I did not know what to do so I rebook myself a flight to Charlotte . It was very inconvenient I not to have anybody form corporate assisting me either from PwC or from kayak . It is a very disappointing experience that American did not wait 1 minute or told me to rebook before making the first flight

It was awful. The communication between corporate and the crew on the ground left more to be desired. The crew even said that Corporate was waiting on answers because they themselves didn't know. Every hour, there was a new excuse. I also understood that passengers were angry, but the crew should have done a better job at crowd control. There was a racial exchange between passengers that could've been avoided has the crew acted sooner.

We sat on plane at gate delayed without communication as to why we were just sitting there

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

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.

Horrible airline! They always got something messed up with their planes. 3 hour delayed made us missed both out flights. Had to wake up early in the morning next morning to get another flight!

Took off over an hour late with multiple mechanical issues. Gate agent in Dallas was lazy and was slow as molasses. Had a line 10 people long. Spirit bad..

The flight was great until towards the end when the flight attendant read an excessively long commercial for purchasing an american airlines credit card. The worst part is that we are doing a lot of traveling this year so i was actually interested in getting the credit card, but I was so annoyed with the long commercial that I completely dismissed the flight attendant bringing around the information. Next time, keep the sales pitch to 10 seconds and then pass around the brochures!!

Me and my husband experienced very bad in American Airlines. We missed our flight going to Doha. The American Airlines was delayed we arrived already 10:27pm. Supposed to be 9:40 pm. So what they did they rebooked our flight and they gave us a hotel. When we arrived at the hotel the front desk said it was fully booked already. Oh my gosh! I said why did you accept the booking if it's fully booked. The guy said that's American Airlines they just book even it's already full. That's 2am already, we have nothing to do so, we decided to go another hotel. We pay the room, food and taxi. Pls give an action on this matter. Refund our expenses and give us more compensation. Not only our room, food, taxi but also our efforts, tiredness looking for a room that can accommodate us.

I liked the entertainment on JetBlue, the service from JFK to JAX was terrible at best

I usually dont fly JeTBlue and I dont think I will ever do it again. The flight was delayed fee time, nobody was giving us any info at at the airport, gate changing, the slowest and poorly organized boarding ever, rude staff.. huh

Like the variety of entertainment options. One crew member was a little on the rough/rude side. Boarding was a mess, attendants didn't do a great job of helping with the luggage storage and it delayed us a couple of minutes.

Flight is delayed by more than an hour without any reason, the jet blue gates kept changing every 20 mins and there is no proper communication. No ear phones provided in flight, there is a screen with entertainment but what is the use, I have earphones but the console has outdated audio connections, no usb C or bluetooth, they are living 15 years behind

Flight was cancelled, no support at JFK even though it is their main hub.. wait times on the phone was very long

I liked the punctuality, the crew, and overall the whole flight

When I agreed to give up my two seats because of overbooking by the airline, I should have been offered some sort of reward or credit towards a future flight. I was not. It was not until the next day when I mentioned it to a Jet Blue employee that I was advised to call 1-800-JetBlue. So here I am, having done Jet Blue a favor and I had to do the work to find out if I was going to get a credit. Such service

It's not JetBlues fault but there was a smell on the plane (possibly other travelers) and 3 children behind me that never quit whining. Soccor fans that were very loud. Pilot brought the plane down from high altitude quickly, dropping us hu dress of feet at a time. I've never felt that intense of dropping on other airlines (usually fly Southwest Airlines). But I arrived safely and I'm thankful for that.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports