$115 Find Cheap Flights from Oakland to Florida Keys - Compare and Save

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1 adult, Economy, 0 bags

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Cheap Flights from Oakland to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Sort by: Cheapest
Miami
7h 20m2 stops
from $261per person
Key West
11h 01m4 stops
from $812per person
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?

No, with an average price for the route of $393, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from Oakland to Florida Keys is August, when tickets cost $377 (return) on average. On the other hand, the most expensive months are December and November, when the average cost of round-trip tickets is $767 and $716 respectively.

Good to know

Low season

August

Cheapest flight

$115
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 48% 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.

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

 
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
SouthwestOverall score based on 4190 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

8.0 ExcellentGreg, Oct 2025
Read more Southwest reviews

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

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.

We had a nice flight. Boarding was easy, our seats were comfortable and the on board service was pleasant.

Service was great, boarding and exiting went smoothly, and the flight was very pleasant.

Southwest Airlines is behind the times with a woefully inefficient service animal policy that leads to major inconsistency and stress for passengers and crew alike. Despite so many attempts to share feedback and request better support, they bungled it once again and provoked a panic attack in the process, with no apologies or acknowledgment that their crew was failing to adhere to their own inadequate policies. WiFi didn’t work, flight was delayed by an hour, it was about what I’ve come to expect from Southwest these days.

Flights were full but SWA still managed to get everyone loaded and depart on time. No snack or beverage service on the first leg due to turbulance. Seats were clean but very little cushioning. Reasonable amount of leg room.

Our flight to Oakland was great bc the plane was new but it was delayed by 15min not bad at all. Over all it was an 8/10

Our flight to Vegas was delayed by almost two hours - I appreciated the updates but it was a bummer of a start to a celebratory trip. The delays meant we missed our dinner reservations we made a month ago so that was disappointing. Once we got to the gate, though, the crew did all they could to make up for the lost time and to keep it efficient and enjoyable, so I appreciate their efforts!!

There was a problem that delayed boarding for more than 20 min. and once everyone was on board, the plane did not take off for another 30 min. which then made our arrival in Phoenix 1 hour late.

Our two flights from GRR to MDW and MDW to OAK were both delayed due to weather. Be sure to build in a sufficient buffer in the transfer time to account for this type of problem. SW recommends connections as short as 40 min. Don't do this. We had to change concourses in MDW, a pretty long walk, to make our connection. Rule of thumb I use when traveling on flights with multiple legs is for connections of 80 min or more, unless there is no plane change, in which case it doesn't matter.

I always have flown Alaska Airlines because I never had an issues. Their customers service is incredible and an amazing communication.

Flight was canceled in good weather due to mechanical issue. Rebooked to flight to different airport in area that landed 7 hours after initially planned arrival. We had to jump through hoops to get taxi reimbursement given flight landed in different airport at 12:45 am.

My travel mate needed wheel chair assistance getting on and off, and it was excellent. Thank you!

Affirmed my disability by allowing me to board when most accessible. Very parable, helpful and friendly staff. Smooth flight overall! I always fly Alaska when possible! Thank you!

In both halves of the trip (going and returning) there were problems. Not exactly Alaska's fault, but still really difficult. Outgoing flight was canceled and rebooked twice due to a total ground stop of all Alaska's flights. This required me to change airports with minimal notice and I almost missed my flight transferring to the other airport (which was roughly an hour and a half away). On the return, the first leg was delayed by an hour, and the second leg was delayed by nearly 3 hours. This was a rough set of flights and the communication about all of these changes was minimal. Crew did their best however, so no fault there. Other thing to remember is there is no food on Alaska flights unless you pre-order. Take that into account when you choose airlines.

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.

From my interactions with the Oakland airport staff through TSA through the gate agents to the flight crew on Hawaiian they were just so kind professional and helpful.. the only thing I would add would be the they need more help and TSA and on the Hawaiian airlines flight it would be so much nicer for them to play beautiful Hawaiian music on the way over there.. they didn't start playing it until right before we landed..

Staff was very friendly. Flight was on time and arrived early. Flight was comfortable.

Flight Staff: Always great! Checking back vs carry-on: I typically check my bag since so much time is spent stowing the bag, it's heavy, maybe not enough room. Delta is charging $45 to check bags. Yet, the people who have multiple carry-on bags are then asked to check their bags and are offered this service for free. This does not seem fair to a person who is trying to be proactive in improving the process . Boarding: Boarding is always slow and exhausting. With the exception of First Class, Economy, why not board the zone in the back of the plane first??? Seats: Why cross the seat belts? I get that it looks nice, but people waste so much time moving them or sitting on them and then having to move. Seats: On both my flights the seat did not recline. Not a big deal. Smell: There was a horrific smell like the restrooms on my first flight. I thought I was going to be sick. Most flights do not smell great. Does Delta use air purifiers or anything?

DL482 did not wait for about 10 of us including a mother and 3 children when we were in the same terminal on DL486, where we were switching from waiting for a jet bridge fix, to moving to a neighboring gate. I understand taxiing delays are ok either but man. We only needed 5 more minutes. DL482 did not adjust from their times at all. This was my first time with Delta.

The actual flight was smooth and we arrived earlier than expected which was great. The flight attendants gave unclear instructions and were rude. They seemed overwhelmed or flustered for the flight. Inflight service was delayed and unsure why.

There needs to be better accommodations for waiting passengers. A a designated standing space that is separated and away from concourse traffic.

overall the crew onboarding and providing service during our flight was great; they were friendly and helpful. I said ok to the entertainment because there was none, but the crew explained why which was very helpful. I am a diabetic and the type of snacks are not diabetic friendly (full of carbs and sugar). However, I am always prepared because I know the catering is for the larger population.

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

N Everything was perfect from boarding to assistance to baggage in Tampa

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

KUDOS TO ALL THE CREW PROVIDING ASSISTANCE WITH PASSENGERS ON A WHEELCHAIR. ON BOTH FLIGHTS THEY HUSTLED TO TAKE MY RELATIVE TO CONNECTION ON TIME. THEY DESERVE A LOT OF CREDIT!

First time flying JetBlue and my perception changed. Love it.

Very poor help no one answering a question regarding seating. Very rude staff. They don’t care, as if it’s not part of their job. Flight was delayed for no good reason and no apologies given.

The wifi didn't work and I needed to do some work. This was a business trip.

You did a great job rescheduling my cancelled flight. However, you made me pay for two seats for $118 even though the seats on the original flight were free. I think that was a very unfair thing to do.

The flight was on time the crew was courteous that makes for a good flight.

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.

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

They put me on a chair in between two men, one overweight who was almost falling on top of me, and the other was even uncomfortable because I was half falling because of what the other was pushing me. I stayed with. my feet were swollen from fluid retention and from being unable to accommodate myself. it was very uncomfortable. I asked for help but they told me that the flight was full and they couldn't help me. I got off the plane almost unable to walk due to the inflammation. and then at FLL airport I asked for help because I couldn't go to my next flight, which was a connection.

I really liked the way snacks and drinks were available throughout the flight!!! The flight attendants were also all fantastic!

More options for your flight to Florida Keys

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