$76 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 1/16. 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

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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$145
Key West
Key West2 stops$264
Miami
Miaminonstop$145
Key West
Key West2 stops$264

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

Fri, Jan 9 - Mon, Jan 12
Spirit Airlines Logo
5:23 pm - 9:05 pm
BOS
-
MIA
3h 42mnonstop
Spirit Airlines Logo
7:00 am - 11:57 pm
MIA
-
BOS
16h 57m2 stops
$145Spirit Airlines
Tue, Jan 20 - Tue, Feb 3
Multiple Airlines Logo
6:00 am - 12:47 pm
BOS
-
MIA
6h 47m1 stop
Multiple Airlines Logo
1:01 pm - 1:03 am
MIA
-
BOS
12h 02m2 stops
$146Multiple Airlines
Mon, Jan 12 - Fri, Jan 16
Multiple Airlines Logo
6:00 am - 7:46 pm
BOS
-
MIA
13h 46m2 stops
Multiple Airlines Logo
5:09 pm - 1:13 am
MIA
-
BOS
8h 04m1 stop
$147Multiple Airlines
Thu, Jan 8 - Fri, Jan 16
Multiple Airlines Logo
6:00 am - 7:46 pm
BOS
-
MIA
13h 46m2 stops
Multiple Airlines Logo
12:56 pm - 4:19 pm
MIA
-
BOS
3h 23mnonstop
$148Multiple Airlines
Fri, Jan 16 - Tue, Jan 20
Multiple Airlines Logo
5:27 pm - 11:56 am
BOS
-
MIA
18h 29m2 stops
Multiple Airlines Logo
12:56 pm - 4:19 pm
MIA
-
BOS
3h 23mnonstop
$149Multiple Airlines
Tue, Jan 6 - Tue, Jan 13
United Airlines Logo
5:20 am - 3:17 pm
BOS
-
EYW
9h 57m2 stops
United Airlines Logo
6:05 pm - 11:49 pm
EYW
-
BOS
5h 44m1 stop
$264United Airlines
Tue, Mar 3 - Fri, Mar 13
Delta Logo
11:15 am - 7:42 pm
BOS
-
EYW
8h 27m1 stop
Delta Logo
7:35 am - 4:18 pm
EYW
-
BOS
8h 43m1 stop
$268Delta
Fri, Jan 9 - Fri, Jan 16
United Airlines Logo
5:45 am - 3:17 pm
BOS
-
EYW
9h 32m2 stops
United Airlines Logo
2:25 pm - 11:49 pm
EYW
-
BOS
9h 24m2 stops
$271United Airlines
Mon, Jan 19 - Fri, Jan 23
JetBlue Logo
8:09 am - 12:05 pm
BOS
-
EYW
3h 56mnonstop
JetBlue Logo
1:00 pm - 4:36 pm
EYW
-
BOS
3h 36mnonstop
$273JetBlue
Tue, Feb 3 - Wed, Feb 11
Delta Logo
6:50 am - 7:40 pm
BOS
-
EYW
12h 50m2 stops
Delta Logo
7:10 am - 2:20 pm
EYW
-
BOS
7h 10m1 stop
$275Delta
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 $193 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 $193.

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 $427, 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 $327 and $307 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 51% 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$76
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly with an average 11% 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.

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

    The cheapest time of day to fly to Florida Keys is generally at night, when round-trip flights cost $245 on average. Morning departures are around 10% 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 $536.

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 $169 one-way - $285 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 8010 reviews
7.9Entertainment
7.9Comfort
7.3Food
8.1Boarding
8.5Crew
Airline reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

6.0 GoodJeff, Dec 2025
JFK - MIA
Read more Delta reviews

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

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.

I truly love flying with Delta. They have always treated me with the upmost respect

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.

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

My issue was with TSA agents for delta airlines. My luggage got flagged. The agent was going thru another persons first. He took 20 min to go thru hers. I asked them to bring mine closer so I could sit down . They said you can go sit it will be fine. I said I am supposed to keep my eyes on my bags at all times. The agent was meticulously unwrapping 2 gifts that the lady had and then tried to re warp it. He was trying to be kind i get it but 20 min for me to stand watching him do that was ridiculous. It was 6 am and there were a ton of travelers. Mine was flagged for some air packed tea that I bought in Turkey. My previous delta flight and 2 others before didn’t flag it. Consistency would be nice. Also on the flight the window shades were down for take off and landing - I thought that was very odd I thought they had to remain open for take off and landing.

The flight was an hour and a half late departing which was inconvenient

The flight was great. The gate location was way to far away!!!

The flight attendant in first class was beyond rude and didn't care at all about her job. AND the gate agent was even worse than the flight attendant for rudeness. She was awful.

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

We didn't take off until an hour after we boarded.

Wish they had the seat-back video screens for watching movies or playing games.

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.

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

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.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

Communication since no reason or explanation was given for 3 hrs delay

We had to sit and wait for almost an hour after landing and taxiing to the gate. The jet bridge was broken so we just waited and waited and waited and it was inconvenient, hot, and unnecessary.

Flight was canceled and instead of rescheduling at the gate we had to go out to the ticket counter. Unruly kids kicking the back of my rows chair with staff to inattentive to say something.

I love a flight without turbulence and you guys deliver It’d be nice to have comfier seats and maybe some inflight entertainment and snacks but that’s for Delta

Terrible Airline I will never fly that airline again. Shame on you for recommending them.

I didn't eat, so I can't rate the food. Delayed set off was beyond

I hope you continue to be one of the great company

I stopped flying spirit as much because they are crooks and thieves. It's not like other airlines where you can at least get credits they just take your money.

The pilot would speak it was painfully load a d the crew had to know this! Maybe the were hesitant to tell him. It was just a mediocre experience and I was in Spirit first class!

My flight was cancelled last minute and I had to pay $1600 for flights, when my original flights were $300. It was a terrible experience.

Horrible, delay after delay due to our plane needing fuel.

Not clean and was told I would get a great seat and it was not great at all

Flight got delayed for 5 hours no good explanation was offered ;(

Horrible. I would never fly Frontier again. The booking process is tricky at best, but fraudulent in my opinion. Frontier customer service did nothing to rectify my purchase -- I ended up paying more than double what I could have gotten from other airlines and nearly triple what I thought I was buying from Frontier. Their booking practices are unfair to the consumer.

Delayed. Text notifications were slow. Not much information o what was happening. Boarding was slow and confusing. Wasn’t even offered water other flight. Had to ask. No entertainment at all. Felt like.a Greyhound bus.

When I wanted to check in 3 hours prior to boarding time, the employees mentioned “a little over an hour delay” so I waited for an hour then I went to go look for food in the terminal and most people from that flight were in the same area looking for food. Finally I decided after food to check to see if it’s anytime closer and now it’s 2 mins until boarding closes?! What are you kidding me? I didn’t receive anything via sms about boarding now nor via email or on the intercom. I luckily made it through, barely, and then there’s no room for my carry on mind you I’m in the very first row so I had to place my purse in one further row back and my carry on sections down. Not sure who pays for better seats to get your stuff placed all over the plane but that was the worst experience I’ve ever had flying with anyone.

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.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Frontier is the Walmart of airlines. Frontier has removed adjustability and comfort from their seats to make the flight lighter and save gas. This makes it impossible to sleep on their flights. Their customer service is abysmal. Once, I bought a drink on the plane, and they swiped my credit card on the plane to pay for it. Then I got three weeks of daily notices from my bank telling me they tried to charge the wrong card number over and over again. I tried to call them, but they removed the ability to actually talk to someone that can resolve such a problem from their company to cut corners. The only way to talk to someone in person is to go to the check-in counter at the airport (40 minutes drive from my house). Eventually their system gave up on trying to charge the card, after 21 days of repeated tries. They don't pad their prices even a little to handle customer service issues like missed flights. They also have a blanket policy preventing helping you reschedule a missed flight if their system says you "cancelled" your own flight online. This is a major problem because their website is broken on mobile devices, the only web browser you have at the airport when their gate staff tell you that you have to reschedule your own missed flight online because they can't help you. I tried to reschedule my flight on my android device and instead, their website crashed and "cancelled" my missed flight. When I got to the counter, the agent argued with me for 5 minutes insisting that I intentionally cancelled my own flight (implying I had to buy another flight). She missed the point: the problem was that I could not buy another flight because their website is broken. I left to avoid more conflict with the "customer service" agent. I tried to redress my issue with their only other "customer service" chanel available: the contact form on their website. The response I got was more of the same: you cancelled your own flight, according to our website / computer records, therefore we won't help you. I was trying to explain the problem with their broken website that cost me hundreds of dollars by crashing / malfunctioning and resulting in a cancelled flight, but they only had deaf ears for this problem. Worst customer service I have ever experienced. I will never buy another Frontier flight again, because it is a risky, painful move that I will likely regret often.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports