$113 Find Cheap Flights from Boston 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 Boston to Florida Keys departing on 9/12. 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 Boston to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami2 stops$232
Key West
Key West2 stops$259
Miami
Miami2 stops$232
Key West
Key West2 stops$259

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

Sat, Sep 5 - Sat, Sep 12
Frontier Logo
12:45 pm - 8:29 am
BOS
-
MIA
19h 44m
2 stops
Frontier Logo
5:22 am - 11:59 am
MIA
-
BOS
6h 37m
1 stop
$232Frontier
Sat, Sep 5 - Sat, Sep 12
Frontier Logo
12:45 pm - 8:29 am
BOS
-
MIA
19h 44m
2 stops
Frontier Logo
5:22 am - 11:59 am
MIA
-
BOS
6h 37m
1 stop
$233Frontier
Wed, Oct 7 - Wed, Oct 14
American Airlines Logo
5:00 am - 8:27 am
BOS
-
MIA
3h 27mnonstop
American Airlines Logo
9:40 pm - 12:59 am
MIA
-
BOS
3h 19mnonstop
$238American Airlines
Wed, Oct 7 - Tue, Oct 13
American Airlines Logo
11:08 am - 2:39 pm
BOS
-
MIA
3h 31mnonstop
American Airlines Logo
9:40 pm - 12:59 am
MIA
-
BOS
3h 19mnonstop
$238American Airlines
Wed, Oct 7 - Tue, Oct 13
Delta Logo
7:15 am - 10:52 am
BOS
-
MIA
3h 37mnonstop
Delta Logo
7:59 pm - 11:33 pm
MIA
-
BOS
3h 34mnonstop
$238Delta
Sat, Aug 29 - Tue, Sep 1
Delta Logo
7:20 am - 10:52 am
BOS
-
MIA
3h 32mnonstop
Delta Logo
7:58 pm - 11:36 pm
MIA
-
BOS
3h 38mnonstop
$238Delta
Tue, Sep 8 - Sat, Sep 12
United Airlines Logo
7:05 am - 2:51 pm
BOS
-
MIA
7h 46m
1 stop
United Airlines Logo
7:00 am - 12:47 pm
MIA
-
BOS
5h 47m
1 stop
$239United Airlines
Tue, Sep 29 - Wed, Sep 30
United Airlines Logo
5:45 am - 2:59 pm
BOS
-
MIA
9h 14m
2 stops
United Airlines Logo
1:26 pm - 7:06 pm
MIA
-
BOS
5h 40m
1 stop
$242United Airlines
Wed, Aug 26 - Sat, Aug 29
Southwest Logo
2:10 pm - 8:10 pm
BOS
-
MIA
6h 00m
1 stop
Southwest Logo
6:30 am - 2:10 pm
MIA
-
BOS
7h 40m
1 stop
$258Southwest
Sat, Aug 29 - Mon, Aug 31
Southwest Logo
5:50 am - 1:35 pm
BOS
-
MIA
7h 45m
1 stop
Southwest Logo
7:15 am - 2:55 pm
MIA
-
BOS
7h 40m
1 stop
$258Southwest
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 5 days was to Key West, at $317 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 5 days was $317.

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 $338 on average. Morning departures are around 15% 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 $579.

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 $511, 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 $214 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $392 and $379 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 Tuesday, as it's usually the priciest day. When flying back from Florida Keys, Friday is the cheapest day to fly and Sunday 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 41% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 4 weeks before departure.

Good to know

Low season

June

Cheapest flight

$113
Best time to beat the crowds but there is an average 11% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Boston to Key West

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 $240 one-way - $369 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.
7.8
DeltaOverall score based on 8497 reviews
8.5Crew
7.8Entertainment
7.8Comfort
7.2Food
8.1Boarding
Airline reviews

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

2.0 MediocreBruce, Jul 2026
BOS - LGA
Read more Delta reviews

Flight from Savannah arrived very late and we did not take off till 2 hours after scheduled departure!

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

Flight attendant was very poor in taking care or showing attention. I slept up front for a few and missed the snacks. She saw me many times, went by me many times and never once asked if I needed anything. The whole 2 hours flight. And this is to a Diamond member in first.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

this crew didn't care much. bumping carts into seats more times than i care to remember

Everything was fine except the entertainment was not working for half of the flight.

Don't waste your money or points on first class. Delta first class is a joke. The seats were rickety, the food was awful, and nothing worked, wifi, my light, the power plug - and it was dirty - the fold out table was gross. For 2-3 hours, tough it out in Economy.

They did a fine job. Can't wait to use Delta in the future.

I would have preferred a flight voucher and to hop on a different flight. Delayed over 6 hours.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Food was great. Staff was phenomenal. Seats were a bit hard and could use a lot more entertainment options as far as movies to choose from. WiFi was good. Overall great trip.

The flight was delayed, they didn’t even have water for the toilets or for drinks

It’s always a great time flying with united airlines.

Very old flight - time to retire it for newer airplanes

2+ hours delayed Outlet in row 12 did not work Tv monitors did not work Lights kept off the entire flight for at 5pm-7pm flight

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

They brought an empty plane to the gate. Then a flight delay was announced for maintenance and waiting on a part. I was then put on a flight to San Francisco instead with a connecting flight to my final destination. Arrived at my final destination 2 hours late.

Excellent service despite turbulence during the flight. Flight attendants were remarkable!

They have overselled the ticket and kicked me out from boarding, All my Plans were collapsed and important network meeting missed.also I booked direct flight i have to go through an 1 stop and it was frustrated.

Horrific. We were delayed due a flight attendant stuck in traffic en route to the airport. Over 100 people were then stuck in Charolette. Then I ran to make my layover only to find that my connection didn’t have a plane anymore. Waited 2.5 hours without any updates. On the flight we had to beg for even a pretzel option.

Terrible boarding and first class experience. Nice staff but overall disorganized, dirty plane.

The flight was delayed significantly and we sat on runway after landing for awhile. Best thing was the flight attendant, Jenny, in first class, who was very professional and attentive. She was excellent - the rest of the flight was not.

Early departure meant on time arrival. Only real problem was free internet had issues, although chatting with the internet help desk (you can do this via aainflight.com) got the issue resolved.

The staff and service on American Airlines were truly outstanding. I had requested wheelchair assistance for my mother due to her knee issues, and the team went above and beyond every step of the way—from boarding in Boston to our arrival in Chicago. Their care, professionalism, and attentiveness made the entire experience smooth and stress-free. I’m very grateful for the support they provided.

Found that the plane used for this short flight is smaller and therefore the seats are really squeezed tight.

Great experience. Good dinner and service. FA's were very nice and attentive.

Jill was the flight attendant in first class she was fabulous!! Best flight attendant I have had in years.!! And I fly every other week. Other can learn from her!!

The business steward was absolutely amazing! Smiles and kindness! Wish all AA flights are like this one!

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Messy plane that was falling apart Small screens that didn't work

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

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.

My JetBlue experience was nice. The flights ran on time, the aircraft was clean and comfortable, and the flight attendants were attentive. My only issue, which is isolated to the low-cost (budget) option at JetBlue, is that the check in process makes the user feel that they have to buy their seats. The seats offered for purchase are upgrades from the budget seats you get (which are essentially the last seats remaining). The interface should not make it feel like you must purchase a seat.

It took 1-1/2 hours to get our luggage after we landed. That to me is unacceptable

The crew was openly hostile and condescending to the customers. They spent the majority of that time in the rear talking and seemed really agitated when people asked questions. I heard five different people told that the information they requested was in the handout or safety brief.

ticketing issues caused many customers to have to go back to check in after waiting in security, then go through security line again.

The flight was great . But you only had one vegan item on the whole flight and someone prior to me took it . I was so disappointed cause I came in from the flooded area and couldn’t pick up anything prior to my flight .

Plane was hot and miserable and the crew was rude!

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

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 !!!!!!!

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.

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

It was impossible to change a carry-on for a checked bag after the initial selection. The flight was delayed 14 hours "to allow for a late arriving aircraft." The seats were shockingly uncomfortable. This was only the second time I've seen seats that didn't recline in an airline. The first was in an East Bloc airline before the fall if the Iron Curtain.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports