
Find the latest flights to Florida Keys in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 7,457,451 searches and data was last updated on September 10, 2026.
Popular in | August |
|---|---|
Cheapest in | January |
Average price | $241 |
Round-trip from | $234 |
One-way from | $116 |
Fly from
Route
Depart
Return
New WindsorKey West
SWF New Windsor Stewart - EYW Key West
SWFEYW
New Windsor Stewart
Sat 10/10
12:39 pm-10:19 am
2 stops21h 40m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorMiami
SWF New Windsor Stewart - MIA Miami
SWFMIA
New Windsor Stewart
Wed 11/4
12:39 pm-9:31 pm
2 stops8h 52m
Miami
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorMiami
SWF New Windsor Stewart - MIA Miami
SWFMIA
New Windsor Stewart
Sat 11/7
12:39 pm-10:29 am
2 stops45h 50m
Miami
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorKey West
SWF New Windsor Stewart - EYW Key West
SWFEYW
New Windsor Stewart
Thu 11/5
11:00 am-9:24 am
2 stops46h 24m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorKey West
SWF New Windsor Stewart - EYW Key West
SWFEYW
New Windsor Stewart
Thu 11/12
11:00 am-2:08 pm
2 stops27h 08m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorKey West
SWF New Windsor Stewart - EYW Key West
SWFEYW
New Windsor Stewart
Thu 11/12
5:27 pm-2:08 pm
1 stop20h 41m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorMiami
SWF New Windsor Stewart - MIA Miami
SWFMIA
New Windsor Stewart
Wed 10/21
12:39 pm-9:29 pm
2 stops8h 50m
Miami
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorKey West
SWF New Windsor Stewart - EYW Key West
SWFEYW
New Windsor Stewart
Sat 11/7
12:39 pm-11:21 am
2 stops22h 42m
Key West
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorMiami
SWF New Windsor Stewart - MIA Miami
SWFMIA
New Windsor Stewart
Sat 10/3
12:39 pm-5:59 pm
2 stops29h 20m
Miami
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
New WindsorMiami
SWF New Windsor Stewart - MIA Miami
SWFMIA
New Windsor Stewart
Thu 10/29
10:38 am-10:29 am
2 stops23h 51m
Miami
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
Everything you need to know about your flight to Florida Keys
Crew
Entertainment
Overall
Food
Boarding
Comfort
Reviews
Barney,May 2026
JFK - ATL
Crew
Entertainment
Overall
Food
Boarding
Comfort
Reviews
Barney,May 2026
JFK - ATL
Crew
Entertainment
Overall
Food
Boarding
Comfort
Reviews
Barney,May 2026
JFK - ATL
Crew
Entertainment
Overall
Food
Boarding
Comfort
Reviews
Barney,May 2026
JFK - ATL
Crew
Entertainment
Overall
Food
Boarding
Comfort
Reviews
Barney,May 2026
JFK - ATL
Crew
Entertainment
Overall
Food
Boarding
Comfort
Reviews
Barney,May 2026
JFK - ATL
The Florida Keys is a year-round travel destination known for its warmth, sunshine and near-perfect beach weather. Travel to the Florida Keys is most popular November to February when the Northerners are looking to escape the frigid winter cold. But this is also when flights to the Florida Keys are most expensive.For cheap flights to the Florida Keys, book your Florida Keys travel during June-August and September-November. At the peak of summer, the average high is 89º F. The weather is still warm and pleasant but the threat of hurricanes during this time is present.
Peak Season
November to February and March-May are the busiest times in the Florida Keys. The weather is warm, the sun is shining and the beaches are packed with people looking to thaw-out from the cold winter air. The Florida Keys is also a big Spring Break destination so be prepared for crowded Florida Keys flights and hotels if you’re traveling during this time.
Off Season
Smart Floridians know to head to the Florida Keys June-August to “cool off” from the hot and humid air inland. But this is also hurricane season (August – November) so the weather can change in a second. However, it’s likely you’ll find cheap flights to the Florida Keys and discounted hotels and resorts during these months, when the peak tourist season has ended.
The best way to explore the Florida Keys is by car, but the Overseas Highway can be extremely busy, particularly at weekends and over holiday periods, so patience is required. This is the only main road in and out of the Keys. In Key West, parking can be difficult; park-and-ride shuttles and taxis are available and recommended.
Buses are available as well. The Dade-Monroe Express bus runs from Key Marathon to Florida City, offering round trips on the hour and stopping on demand. Greyhound runs a Keys shuttle bus several times a day between Miami International Airport, stopping at all major points along the Keys.
Cycling is a pleasant way to explore the individual Keys, and scooter rentals are also popular.