$99 Find Cheap Flights from Oakland 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 Oakland to Florida Keys departing on 8/24. 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

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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Oakland to Florida Keys, 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 Oakland to Florida Keys, as well as popular online travel agencies
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Cheap Flights from Oakland to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$187
Key West
Key West2 stops$889
Miami
Miami1 stop$187
Key West
Key West2 stops$889

Book Cheap Oakland 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 Oakland 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 Oakland to Florida Keys

Mon, Oct 27 - Thu, Oct 30
Southwest Logo
5:35 am - 6:15 pmOAK-MIA
9h 40m1 stop
Southwest Logo
5:00 pm - 12:05 amMIA-OAK
10h 05m1 stop
$187Southwest
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Thu, Sep 4 - Wed, Sep 10
Spirit Airlines Logo
6:30 am - 6:55 pmOAK-MIA
9h 25m1 stop
Spirit Airlines Logo
7:20 pm - 1:34 pmMIA-OAK
21h 14m1 stop
$192Spirit Airlines
Find Deal
Thu, Sep 4 - Wed, Sep 10
Spirit Airlines Logo
6:30 am - 6:55 pmOAK-MIA
9h 25m1 stop
Spirit Airlines Logo
7:00 am - 11:32 pmMIA-OAK
19h 32m2 stops
$216Spirit Airlines
Find Deal
Thu, Sep 4 - Tue, Sep 9
Spirit Airlines Logo
6:30 am - 6:55 pmOAK-MIA
9h 25m1 stop
Spirit Airlines Logo
8:04 pm - 11:32 pmMIA-OAK
30h 28m3 stops
$218Spirit Airlines
Find Deal
Fri, Sep 5 - Thu, Sep 11
Spirit Airlines Logo
6:30 am - 6:55 pmOAK-MIA
9h 25m1 stop
Spirit Airlines Logo
7:23 pm - 1:34 pmMIA-OAK
21h 11m1 stop
$226Spirit Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
Southwest Logo
5:15 am - 6:10 pmOAK-MIA
9h 55m1 stop
Southwest Logo
5:00 pm - 12:05 amMIA-OAK
10h 05m1 stop
$256Southwest
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Sat, Oct 25 - Wed, Oct 29
Delta Logo
5:59 pm - 6:21 amOAK-MIA
9h 22m1 stop
Delta Logo
6:45 pm - 11:53 pmMIA-OAK
8h 08m1 stop
$257Delta
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Tue, Oct 28 - Wed, Oct 29
Delta Logo
4:51 pm - 9:35 amOAK-MIA
13h 44m2 stops
Delta Logo
6:45 pm - 11:53 pmMIA-OAK
8h 08m1 stop
$262Delta
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Tue, Oct 7 - Mon, Oct 20
Alaska Airlines Logo
6:40 am - 5:29 pmOAK-MIA
31h 49m1 stop
Alaska Airlines Logo
6:46 pm - 10:23 amMIA-OAK
18h 37m1 stop
$265Alaska Airlines
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Thu, Oct 16 - Mon, Oct 20
Alaska Airlines Logo
6:40 am - 5:29 pmOAK-MIA
31h 49m1 stop
Alaska Airlines Logo
6:46 pm - 10:23 amMIA-OAK
18h 37m1 stop
$279Alaska Airlines
Find Deal
Booking Insights

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

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

Can I save money by flying with a layover from Oakland 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 $568, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Oakland 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 Oakland to Florida Keys is September, when tickets cost $230 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $522 and $507 respectively.

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

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

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

How far in advance should I book a flight from Oakland 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 Oakland 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 Oakland to Florida Keys, you should book around 2 weeks before departure, which saves you about 6% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 6 weeks before departure.


Good to know

Low seasonMay
Cheapest flight$99
Best time to beat the crowds with an average 38% drop in price.
Most popular time to fly with an average 26% increase in price.
Flight from Oakland to Miami

FAQs - booking Florida Keys flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Oakland 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 Oakland 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 Oakland 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 Oakland 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 Oakland 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 in the morning, when round-trip flights cost $359 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. 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 $397.

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

 
See real verified KAYAK customer reviews for airlines flying from Oakland 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 Oakland 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
Alaska AirlinesOverall score based on 10000 reviews
7.1Entertainment
8.5Crew
7.8Comfort
8.1Boarding
7.1Food
Airline reviews

Crew was not happy to be there and neither was I 😭 well at least the lady that helped me.. I was stuck in the middle seat between two men. Totally my fault since I didn’t pay a fee to select my seat though. I recommend paying the fee even if you’re in a budget. It’s better than being placed aaaaallllllll the way in the back next to the smelly bathrooms. The seats didn’t recline either!! It was a red eye flight so I got no sleep whatsoever. Ordered a coffee and it tasted like…. Let’s just say it was horrible. I had to to return it to the same crew lady and she looked at me like this girl…. Sorry but I was not going to drink that- please take it back!! Oh and lastly, my luggage was completely broken and damaged. All wheels were missing by the time my luggage came around in the luggage cart. Lmao. Overall poor experience to say the least. Tickets were cheap though😂😂😂

6.0 GoodMayra, Aug 2025SFO - EWR
Read more Alaska Airlines reviews

Crew was not happy to be there and neither was I 😭 well at least the lady that helped me.. I was stuck in the middle seat between two men. Totally my fault since I didn’t pay a fee to select my seat though. I recommend paying the fee even if you’re in a budget. It’s better than being placed aaaaallllllll the way in the back next to the smelly bathrooms. The seats didn’t recline either!! It was a red eye flight so I got no sleep whatsoever. Ordered a coffee and it tasted like…. Let’s just say it was horrible. I had to to return it to the same crew lady and she looked at me like this girl…. Sorry but I was not going to drink that- please take it back!! Oh and lastly, my luggage was completely broken and damaged. All wheels were missing by the time my luggage came around in the luggage cart. Lmao. Overall poor experience to say the least. Tickets were cheap though😂😂😂

Overall it was good. There was a delay in departure, which is why I did not rate it as excellent.

Departing flight to San Diego was delayed. Return flight from SD to SBP was delayed. Not terrible but not ideal

I always heard this was a terrible airline but I was happy to experience otherwise. The seats were more comfortable than delta. They did board late and gate was a little chaotic, which is to be expected for a budget airline. I would definitely do it again for that price.

My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.

Canceled flight. No communication of this prior. Rescheduled to next day. Our good seats we purchased months ago turned into last row middle. No apology, reason, nor compensation for time and $ spent.

delayed flight 3 hours, then took 45 min to get to gate and another 10 min to open door

The setting on the loudspeaker was painful and the crew member who did the talking spoke very quickly and repetitively, with extra little jokes that were distracting and mostly unfunny. I doubt that the main messages penetrated the noise.

The Alaska app and website were not fully operational. I had to spend about 15 minutes at the counter doing things that should have been completed online. The agent was very nice and helpful, however.

Good. They checked my bag FOR FREE so I didnt have to try to hoist it up into the overhead compartment. Also, they served free beverages, which I appreciated.

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.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

It is southwest seat was ok. Not the most comfortable seat

Plz don't take away free bags and free seating

It was a perfect flight in all aspects! Both legs!

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

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.

Easy boarding with an extremely kind attendant. Seats were spacious and we had 3 seats for 2 people so we could stretch out. Comfortable air flow and very attentive and hospital attendants. Bathrooms and food were the only negative. Bathrooms were so small you could hardly get in and close the door. I don’t think an obese person would fit or a person with a movement disability. Food was the trending food for flights, nonexistent. We spent $40 getting sandwich and snack at airport for our 6 hour flught.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

I liked the choice of lemon ginger tea. I think stewardesses can be more considerate of older people needs.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

Boarded plane and then delayed 1.5 hours while on the plane

I love flying with United. Unfortunately, I flew on an older plane with minimal upgraded technology (no Bluetooth functionality or handy charging ports). Otherwise, the flight was great and even arrived early.

They changed my seats after I checked in and I was stressed from the time I saw that information until just before boarding, when the gate attendant fixed it, but it shouldn't have happened. And if it couldn't be prevented, then the people on the phone I spoke with should have done something to help, which they did not, nor did they offer me compensation, just meaningless apologies.

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

Really good 😊 the woman at the gate entrance was a little rude checking in our carry-on but i dont think she worked for the airline, she worked for the airport at sacramento, other than that amazing.

This gate agents are always so rude! I stopped flirting with spirit years ago for that reason I thought it would change by now. It’s so tacky they try to treat you like a school child i hate it

The staff was very sarcastic, the flight was delayed. There was no wi-fi o any type of entertainment. The plane was dirty and we have to wait a long time for the luggage to come out.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

The air fares are good, Charging me for every single thing 😩

I am very happy with my experience with Spirit Airlines. Both flights were on time. Boarding was very pleasant. Crew was very nice. Flights were amazing and we even arrived earlier than the schedule time. I am hoping Spirits keeps on having non stop flight from Ft Lauderdale to Hartford for many years to come.

you guys canceled my flight last minute and lost my luggage.

Didn't like size of seats. Found charges for checked luggage and carry on too high

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Prepaid for 1 bag but my prior airline did not provide it to me in time to check it with Spirit and I could not get my $75 refunded.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

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