$115 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 3/31. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Florida Keys

 
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$229
Key West
Key West2 stops$753
Miami
Miami1 stop$229
Key West
Key West2 stops$753

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, Apr 13 - Wed, Apr 15
Southwest Logo
11:55 pm - 11:55 am
OAK
-
MIA
9h 00m
1 stop
Southwest Logo
1:25 pm - 7:50 pm
MIA
-
OAK
9h 25m
1 stop
$229Southwest
Mon, Apr 13 - Wed, Apr 15
Southwest Logo
11:55 pm - 11:55 am
OAK
-
MIA
9h 00m
1 stop
Southwest Logo
1:25 pm - 8:20 pm
MIA
-
OAK
9h 55m
2 stops
$234Southwest
Sun, Apr 26 - Wed, Apr 29
Southwest Logo
11:55 pm - 1:10 pm
OAK
-
MIA
10h 15m
2 stops
Southwest Logo
6:40 am - 2:55 pm
MIA
-
OAK
11h 15m
2 stops
$239Southwest
Mon, Apr 13 - Wed, Apr 15
Southwest Logo
11:55 pm - 11:55 am
OAK
-
MIA
9h 00m
1 stop
Southwest Logo
1:25 pm - 7:50 pm
MIA
-
OAK
9h 25m
1 stop
$249Southwest
Mon, Apr 13 - Wed, Apr 15
Southwest Logo
11:55 pm - 11:55 am
OAK
-
MIA
9h 00m
1 stop
Southwest Logo
1:25 pm - 8:20 pm
MIA
-
OAK
9h 55m
2 stops
$254Southwest
Tue, Mar 24 - Tue, Apr 21
Delta Logo
4:49 pm - 5:40 am
OAK
-
MIA
9h 51m
1 stop
Delta Logo
6:42 am - 11:53 am
MIA
-
OAK
8h 11m
1 stop
$257Delta
Tue, Mar 24 - Tue, Apr 21
Delta Logo
4:49 pm - 5:40 am
OAK
-
MIA
9h 51m
1 stop
Delta Logo
2:45 pm - 11:54 pm
MIA
-
OAK
12h 09m
2 stops
$262Delta
Mon, Apr 13 - Wed, Apr 15
Southwest Logo
11:55 pm - 11:55 am
OAK
-
MIA
9h 00m
1 stop
Southwest Logo
1:25 pm - 7:50 pm
MIA
-
OAK
9h 25m
1 stop
$264Southwest
Tue, Mar 31 - Tue, Apr 7
Southwest Logo
11:55 pm - 11:40 am
OAK
-
MIA
8h 45m
1 stop
Southwest Logo
12:10 pm - 9:45 pm
MIA
-
OAK
12h 35m
1 stop
$269Southwest
Tue, Apr 21 - Fri, Apr 24
Delta Logo
5:04 pm - 5:27 am
OAK
-
MIA
9h 23m
1 stop
Delta Logo
6:42 am - 11:53 am
MIA
-
OAK
8h 11m
1 stop
$277Delta
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 $353, 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 May, when tickets cost $235 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $612 and $492 respectively.

Good to know

Low seasonJanuary
Cheapest flight$115
Best time to beat the crowds with an average 27% drop 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 4309 reviews
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

4.0 OkayEmma, Mar 2026
LAX - PHX
Read more Southwest reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

Great flight but super high price. Glad it was a business trip and not personal

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

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.

The whole experience was excellent. As it most often is with Delta

We waited an hour on the runway to get a gate in Orlando

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

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Sorry I didn't realize I was writing a review for each leg. Please see my previous review - it applies to the entire flight, not just a single leg.

boarded at 5:30 pm, pushed away from gate at 6pm ... takeoff was not until ~6:45pm; disappointing

Paid for wifi that didn't work. No plug in seat to work. No entertainment.

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

Comfort Plus seat 11E seemed smaller than prior flights. The movie selection is good. Watched most of the most recent Tron movie. I'll watch the remaining part later as my movie is saved in the Delta Seatback Experience.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

Flight left on time and we arrived 25 minutes early! There was a gate available when we arrived so early on a busy Sunday afternoon! Flight attendants came around twice with the drinks cart.

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

it was a very short flight so my expectations were low.

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

Everything you need to know for your flight to Florida Keys

Information on your arrival and departure airports