$150 Find Cheap Flights from Oakland 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 Oakland to Florida Keys departing on 9/7. 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 Oakland to Florida Keys

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Miami
Miami1 stop$299
Key West
Key West2 stops$577
Miami
Miami1 stop$299
Key West
Key West2 stops$577

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, Sep 14 - Wed, Sep 16
Delta Logo
5:00 pm - 5:49 am
OAK
-
MIA
9h 49m
1 stop
Delta Logo
7:05 am - 11:59 am
MIA
-
OAK
7h 54m
1 stop
$299Delta
Tue, Sep 15 - Thu, Sep 17
Delta Logo
5:00 pm - 5:49 am
OAK
-
MIA
9h 49m
1 stop
Delta Logo
7:05 am - 11:59 am
MIA
-
OAK
7h 54m
1 stop
$299Delta
Tue, Oct 27 - Fri, Oct 30
Southwest Logo
6:35 am - 4:55 pm
OAK
-
MIA
7h 20m
1 stop
Southwest Logo
4:10 pm - 10:35 pm
MIA
-
OAK
9h 25m
1 stop
$299Southwest
Mon, Oct 26 - Fri, Oct 30
Southwest Logo
5:40 am - 6:30 pm
OAK
-
MIA
9h 50m
1 stop
Southwest Logo
4:10 pm - 10:35 pm
MIA
-
OAK
9h 25m
1 stop
$299Southwest
Sun, Sep 6 - Fri, Sep 11
Southwest Logo
11:55 pm - 12:10 pm
OAK
-
MIA
9h 15m
1 stop
Southwest Logo
3:20 pm - 7:45 pm
MIA
-
OAK
7h 25m
1 stop
$299Southwest
Sat, Sep 5 - Wed, Sep 9
Delta Logo
5:00 pm - 6:00 am
OAK
-
MIA
10h 00m
1 stop
Delta Logo
7:05 am - 11:59 am
MIA
-
OAK
7h 54m
1 stop
$299Delta
Sat, Aug 15 - Wed, Sep 30
Delta Logo
5:00 pm - 6:00 am
OAK
-
MIA
10h 00m
1 stop
Delta Logo
7:05 am - 11:59 am
MIA
-
OAK
7h 54m
1 stop
$299Delta
Wed, Sep 9 - Tue, Sep 15
Alaska Airlines Logo
2:15 pm - 5:13 pm
OAK
-
MIA
23h 58m
1 stop
Alaska Airlines Logo
6:16 pm - 9:27 am
MIA
-
OAK
18h 11m
1 stop
$311Alaska Airlines
Wed, Sep 9 - Fri, Sep 11
Alaska Airlines Logo
2:15 pm - 5:13 pm
OAK
-
MIA
23h 58m
1 stop
Alaska Airlines Logo
6:16 pm - 1:19 pm
MIA
-
OAK
22h 03m
1 stop
$335Alaska Airlines
Wed, Sep 9 - Tue, Sep 15
Alaska Airlines Logo
6:01 am - 5:13 pm
OAK
-
MIA
32h 12m
1 stop
Alaska Airlines Logo
6:16 pm - 9:27 am
MIA
-
OAK
18h 11m
1 stop
$335Alaska Airlines
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 $398, 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 January, when tickets cost $285 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $686 and $586 respectively.

Good to know

Low season

September

Cheapest flight

$150
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly with an average 50% 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 3 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
SouthwestOverall score based on 4229 reviews
7.0Food
8.6Crew
8.1Boarding
8.0Comfort
7.5Entertainment
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
OAK - BUR
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.

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

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

No service flight that took 5 hrs and a stop at an unscheduled airport. Crew and pilots did their jobs

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

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

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

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Flight was delayed 5 hours. Updates kept changing. Sears were extremely cramped. Very little leg room. Flight attendant was rushing through with drinks and hit me in the knee either the cart and didn’t apologize. They gave a 15 dollar voucher in airport which doesn’t buy. Much and it was so late that choices were limited.

Always pretty good as far as I see it. Staff was friendly and process was quick to get on and off.

The flight was delayed because they closed several flight ways because of air shows, fire works, etc.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Left an hour and a half after the listed time. Up side was it had TV screens on the seat.

I've been flying American mostly, and it's been very frustrating. This united flight makes me realize maybe the issue isn't flying, but the airline. United was a significantly better experience. The plane was more comfortable, with a normal amount of leg room (vs the ridiculous reductions AA has made), more comfortable seats, screens to watch movies. It was a much better experience!

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports