$55 Find Cheap Flights from Boston to Florida Keys

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Boston to Florida Keys departing on 4/1. 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 Florida Keys

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Florida Keys.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Boston to Florida Keys.
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Cheap Flights from Boston to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miaminonstop$93
Key West
Key West1 stop$273
Miami
Miaminonstop$93
Key West
Key West1 stop$273

Book Cheap Boston 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 Boston 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 Boston to Florida Keys

Sun, Apr 5 - Thu, Apr 9
Spirit Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Spirit Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$93Spirit Airlines
Mon, Mar 30 - Wed, Apr 8
Spirit Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Spirit Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$96Spirit Airlines
Wed, Apr 1 - Wed, Apr 8
Spirit Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Spirit Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$97Spirit Airlines
Wed, Apr 1 - Sat, Apr 4
Spirit Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Spirit Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$98Spirit Airlines
Tue, Apr 14 - Thu, Apr 16
Spirit Airlines Logo
5:49 pm - 9:20 pm
BOS
-
MIA
3h 31mnonstop
Spirit Airlines Logo
10:00 am - 1:17 pm
MIA
-
BOS
3h 17mnonstop
$100Spirit Airlines
Sun, Mar 29 - Sat, Apr 4
Spirit Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Spirit Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$103Spirit Airlines
Tue, Mar 31 - Sat, Apr 4
Multiple Airlines Logo
12:36 pm - 8:07 pm
BOS
-
MIA
7h 31m
1 stop
Multiple Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$105Multiple Airlines
Tue, Apr 14 - Thu, Apr 16
Multiple Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Multiple Airlines Logo
6:00 am - 11:33 am
MIA
-
BOS
5h 33m
1 stop
$106Multiple Airlines
Sun, Mar 29 - Sat, Apr 4
Spirit Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Spirit Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$108Spirit Airlines
Tue, Mar 31 - Tue, Apr 7
Spirit Airlines Logo
6:01 am - 9:34 am
BOS
-
MIA
3h 33mnonstop
Spirit Airlines Logo
10:39 am - 1:55 pm
MIA
-
BOS
3h 16mnonstop
$109Spirit Airlines
Booking Insights

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

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

What is the cheapest Boston to Florida Keys flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Florida Keys from Boston found in the last 72 hours was to Key West, at $247 round-trip. The most popular route is from Boston (BOS) to Key West (EYW), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $247.

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

The average price for all round-trip flights from Boston 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 $281 on average. Morning departures are around 20% more expensive than evening flights, on average. The most expensive time of day to fly to Florida Keys is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $493.

Can I save money by flying with a layover from Boston 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 $456, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Boston 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 Boston to Florida Keys is September, when tickets cost $178 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $361 and $304 respectively.

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

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

If you are looking for a flight deal from Boston to Florida Keys, look for departures on Thursdays and avoid leaving on a Wednesday, as it's usually the priciest day. When flying back from Florida Keys, Thursday is the cheapest day to fly and Monday is the most expensive.

How far in advance should I book a flight from Boston 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 Boston 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 Boston to Florida Keys, you should book around 3 weeks before departure, which saves you about 50% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 3 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$55
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 31% increase in price.
Flight from Boston to Miami

FAQs - booking Florida Keys flights

  • How does KAYAK find such low prices on flights from Boston 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 Boston to Florida Keys.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Boston 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 Boston 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 Boston 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 Boston 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 Boston 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 Boston to the following destinations at these prices or less: Miami $143 one-way - $233 round-trip

Reviews of the top 5 airlines serving from Boston to Florida Keys

 
See real verified KAYAK customer reviews for airlines flying from Boston 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 Boston 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.
7.9
DeltaOverall score based on 8288 reviews
7.9Comfort
8.5Crew
7.8Entertainment
8.1Boarding
7.2Food
Airline reviews

The whole experience was excellent. As it most often is with Delta

10.0 ExcellentRay, Mar 2026
LGA - MCO
Read more Delta reviews

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

Good experience and the flight landed early. There was no food I had or entertainment.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

My check in was stressful. I somehow lost my seat from my original booking, the plane showed no availability/no seat when it was time to check-in. I called and was instructed to try to get a seat at the airport. I asked if it was a full flight and the travel agent said the site showed some seating but was not able to secure one for me. Why not? On my way to the airport the app finally revealed one available seat towards the back of the aircraft that I was able to book. It ended up being an overbooked flight, so glad I wasn't stuck.

Both flights were significantly delayed. The flight experience itself was great.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

It was good. I prefer JB over other airlines.I just wish we had headphones for the films, but other than that - good.

The ride share experience in JFK is terrible. After traveling on a flight, then you need to take a subway to the last stop to get an uber or lyft. Unacceptable. Bad job JetBlue for permitting JFK and Port Authority to do this to your passengers.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

Check in was rough because the check in crew did not know how to manage my international visa documents. Required a long process and 4 people to finally be able to proceed to security. They told us incorrect information several times before acknowledging we did indeed have everything we needed from the start.

Never going to fly your airline again if it can be avoided.

Mechanical issue delayed us 2hrs and then once we landed sat on tarmac for 30mins because someone left a vehicle in front of the gaye

Plane from partner PSA was filthy. Plastic needs to be thoroughly cleaned. Really disgusting to look at and wonder about cleanliness of parts less visible.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

We missed our flight and got stranded in Miami where we had to rent a hotel we could not afford. they would not work with us because they said it was weather related even though the gate attendant said it was not. I could go on but trying to get satisfaction has wore me down, which I believe is the intent. My only solution is to never fly AA again.

Horrendous and unprofessional staff and will never fly spirit again

Sadly the flight was delayed by 4 hours due to the weather snd sir traffic control staffing. Otherwise the crew was amazing and the flight was perfect.

Not enough crew members so we had to wait for more to arrive and they could never give us updates timing. Not even water for free on board. Bare bones airplane- there wasn’t even a seat back pocket to put things into. Spirit is cheap for a reason but this was dismal

The plane was clean and crew was nice. Can’t speak on food as I did not have any

We get stuck in the plane when landed during 45min and no communication from the crew People were listening to their phone and music out loud and nobody told them anything I definitely want stop booking spirit flight it is a disaster

Good: It was cheap and they got us to our destination safely. Not so Good: Gates experience with many, many nauseatingly (almost) threatening announcements about bags size and how much they were going to charge us if our bag was too big, even to the point of having a gate agent roaming around through the passengers eyeballing bags size and making people go check their bags in the sizers.

Everything is an additional fee. No one said anything when I checking in and got my boarding pass about my small carry on suitcase. Charged me $100 at the gate for that little bag that I still had to take with me. Delays for both flights for no reason and then when I asked everyone said something different. Never flying spirit again. If it was just one thing maybe. This was a show from the minute I got to the airport.

Terrible. The flight was randomly delayed in Chicago causing us to miss our connection and they offered us a flight the next day at 6 am and it would have taken till 345 to get to Pensacola. They didn’t cover any fees. Our bags also supposedly were on the flight to Pensacola and we tried to get them yesterday after driving 6 hours and nobody was available. Worst company ever and will never use them again. Had to pay for a rental. Spirit is claiming in climate weather for the delay but there wasn’t any weather issuesz it’s a bunch of bullshit and I am not happy

Checking in at desk in Chicago was horrible. Person was not friendly never smiled and said my flight was not paid for so I had to give another credit card. Then it ended up that I was charged twice. Then after arriving at my destination had to wait on the phone a long time to speak to a person to fix the double charge! Thank goodness the flight was perfect.

The bag situation was confusing. I didn’t know I had to pay for Carry ons. The seats were uncomfortable and there was no entertainment

My flight was originally from SAT to MCO connecting from MCO to ORD. We got diverted to ATL and than Frontier staff there was sooo un helpful first they said they couldn’t give us any accommodation since our flight first got delayed that cancelled and now it’s 221am and I am still in ATL since they said they need to create a new flight my final destination is ORD and I have been delayed twice and cancelled. With no real help the frontier app didn’t work no email updates over all such a horrible experience

There's no seats that lean back with little leg space i wad uncomfortable the entire flight. Your charges for extra baggage is despicable and costly!!

Remind customers of the need to have passport or new ID for boarding.

Flight was canceled. Most upsetting was message from Kayak, stating that the flight was canceled and click with Kayak for details regarding rebook, refund details. THERE'S NO INFORMATION PROVIDED BY KAYAK EXCEPT THAT FLIGHT IS CANCELED. AND NOW THIS SURVEY TO FIND OUT HOW WAS THE FLIGHT !!!!!!!

The flight never took off and we spent 7 hours at the airport

Gate not determined until I got to the airport - hard to plan the trip to the airport.

I am writing to express my disappointment with my recent Frontier Airlines flight. I was charged $99 at the gate because my bag was said to be too large, yet once onboard there was no available overhead bin space, and I was required to place the bag under the seat in front of me anyway. This made the charge feel unnecessary and unfair. Additionally, before the flight even took off, I was asked to move from the seat I paid for into a middle seat so another passenger and her cat could have my seat to themselves. I was not offered compensation or an explanation for being moved from a paid seat. Between the unexpected bag fee and being forced to give up my seat, this experience fell well below acceptable customer service standards. I would appreciate a review of this situation and appropriate compensation.

One of the worst travel experiences I've had. Had a flight scheduled with CVG to RSW on VLSWQX this morning departing at 5:30. Two individuals at the gate and one was in training. Not her fault but she didn't have the ability to check people in resulting in at least 15 families that didn't make it on the plane because they weren't checked into the system in time. When arriving at the airport to drop off our prepaid checked bags, the bag drop off agent asked if we could check our bags at the gate because of the long line. We said no problem so arrived at the gate by 5:00. They told those people that had previously paid for checked bags to stand off to the side while they let others that either didn't have a checked bag or their bag was already on the plan through. Realizing the gate workers had an issue, they either called for help or this lady showed up late for work as she didn't arrive until 5:15. The worker who had been there training the other individual and working diligently to make sure all passengers got on board. He even said that at one point all people that are currently in line are fine but asked the person in training to stand outside the ticketing area around 5:15 to notify any late travels that the flight was in boarding process and they arrrived too late. At that point, we're sill standing off to the side with our pre-paid checked bags patiently waiting. When the new lady arrived she couldn't have been more rude. It was an awful seen. Essentially they had asked for those without an assigned seat to board last, those with pre-paid checked bag stand off to the site and any traveling with a larger items that needed to be checked at the gate (such as a stroller), wait on the side. They realized that the flight needed to leave on time so the gate attendant shut the gate. So anyone without a seat assignment, those that had pre-checked bags, and the worst one I saw was a mother with two infant children was in line with use because she was asked to stand to the side because her stroller. When they shut the door to the plan they told her she could no longer get on. Her checked bags were already on the plane with her car keys in them, and the lady told her we couldn't accept anyone else on because the door was shut. She didn't even have a way to get home from the airport. Truely evil behavior. I've flown Frontier enough to know customer service is not a top priority in the company's mission, but this was an all-time low. I'm sending this after an 18 hour drive that our family just completed to Bonita Springs . I felt really bad for the lady being trained and the other individual trying to help, but when the new lady came to the gate she was truly one of the rudest individuals I've ever met. One lady had been there since 4am but because she didn't have an assigned seat they wouldn't let her on the plan.

I loved the staff on the plane. So friendly and helpful! However, there was an argument and misunderstanding by the staff and a customer at the gate, and the staff member was being unprofessional. When we arrived in Atlanta, we waited 1.5 hrs for our luggage to arrive. When I asked the airport attendant, they said Frontier had the longest wait for luggage out of any airlines, and that they could not be held responsible for the delay.

Better than expected. Staff were friendly and nice on both flights.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports