Best Time to Visit Key West: Weather, Prices, Crowds

When is the best time to visit Key West?

There is no cold month in Key West, but there are expensive months and stormy ones. The island sits at the southernmost end of the Florida Keys, about 90 miles from Cuba, so even January averages a high of 75.8°F. What changes through the year is the price of a room, the size of the crowds and the amount of rain.

Here is how the year breaks down, with our view on each season.

What is the weather in Key West by month?

February and March are the driest months, each averaging just over 1.5 inches of rain. September is the wettest at 7.24 inches, and August is the hottest, with an average high of 90.6°F. January is the coolest month, with nights averaging 65.5°F, so pack a light layer for evenings on the water.

Summer rain usually comes as afternoon storms rather than all-day rain, which is why so many summer plans put the beach and the boat trips in the morning.

When is hurricane season in Key West?

Hurricane season runs from 1 June to 30 November. The highest risk is from August to October, the same months that bring most of the island's rain. That does not mean you should never go in summer or fall, but it does mean your plans need room to change.

Only one highway runs down the Keys to Key West, and Monroe County, which covers the Keys, can order visitors to leave ahead of a storm. Our advice for any trip between June and November: book a refundable room, look at travel insurance before you pay, and watch the National Hurricane Center forecast in the week before you fly.

When is Fantasy Fest, and should you plan around it?

Fantasy Fest is a 10-day costumed street carnival held every year in late October. In 2026 it ran from 16 to 25 October, and for those ten days Old Town fills with crowds and partygoers. The event is aimed at adults.

If Fantasy Fest is the reason for your trip, book your room months ahead, because the island is at its fullest. If you want a quiet trip with children or an easy dinner reservation, we'd pick a different week. The festival sets its dates each year, so confirm next year's dates on the official Fantasy Fest website before you book flights or a hotel.

When is Key West cheapest?

Key West is one of Florida's most expensive vacation spots in any month, and hotel rates rise highest in the winter high season, when the weather is best. Rates are usually lower in summer and early fall, when the heat, the afternoon storms and hurricane season keep many visitors away. Fantasy Fest week in late October is the exception.

We don't have our own fare check for Key West yet, so we won't name a cheapest month to fly; we'd rather say so than guess. What we can say is that flights into Key West International (EYW) are usually pricier than flights into the big mainland airports. Price Miami (MIA) and Fort Lauderdale (FLL) for the same dates before you book.

Should you fly into Key West or drive from Miami?

Key West International (EYW) has direct flights, and as of October 2026 American, Delta and United all fly in from their hubs, including Delta from Atlanta (ATL), American from Miami and Charlotte (CLT), and United from Newark (EWR) and Houston (IAH). Schedules change by season, so check the airline's website for your dates.

The alternative is the Overseas Highway (U.S. 1), which links the islands with a chain of bridges, including the Seven Mile Bridge near Marathon. From Miami the drive takes about 3.5 to 4.5 hours in good conditions, and longer in traffic. Key West is also a popular cruise port, so expect Old Town to be busier on days when ships are in.

Our take: for a trip of 3 nights or fewer, fly into EYW if the fare gap is small, because the drive costs most of a day each way. For a week, or if you want to see more of the Keys, a cheaper Miami fare plus the drive often makes sense.

If you drive, these stops on the way are worth the time.

• Islamorada and Key Largo: the upper Keys, known for sportfishing, scuba diving and coral reefs.
• Marathon: boating, fishing and the Turtle Hospital, which runs sea turtle rescue tours.
• Big Pine Key: the National Key Deer Refuge, home to the endangered miniature Key deer.
• Bahia Honda State Park: about 45 to 60 minutes northeast of Key West, with natural beaches, clear water and views of the old broken railroad bridge.

What is there to do in Key West in each season?

Set your expectations on beaches first. Key West's shoreline is mostly rocky or taken up by docks and harbors, not miles of wide sand. The island makes up for it with history, the reef and its sunsets.

• Any time of year: the Mallory Square Sunset Celebration every evening, with street performers and vendors; the Ernest Hemingway Home and Museum, the author's 1930s home, with its six-toed cats; and the 88 steps up the Key West Lighthouse for a 360-degree view of the island.
• Winter and spring: a full-day trip by ferry or seaplane to Dry Tortugas National Park, 70 miles west, to see Fort Jefferson and the coral reefs; and walking or cycling the Old Town lanes while the weather is cooler.
• On the reef: the Florida Reef is the only living coral barrier reef in continental North America, and you reach it on a guided snorkel or charter boat trip.
• Beach time: Fort Zachary Taylor Historic State Park has the island's best beach, with shaded picnic spots and a Civil War fort, but bring water shoes for the rocks. Smathers Beach is the longest sandy beach, though wind and seaweed vary by day.
• Summer storm afternoons: the Key West Butterfly and Nature Conservatory, with more than 50 butterfly species and flamingos; the Florida Keys Eco-Discovery Center; and the Harry S. Truman Little White House.

The Southernmost Point buoy, marked "90 Miles to Cuba", is the island's most photographed spot. Lines can run over an hour at peak times, so go early in the morning.

How should you spend 3 days in Key West?

Key West is compact, so three days covers the main sights without rushing. This plan works in any season; in summer, move the outdoor parts to the morning.

1. Day 1, Old Town and sunset: an early photo at the Southernmost Point, then the Hemingway Home and the Key West Lighthouse. Walk the Old Town lanes and Duval Street in the afternoon, catch the sunset at Mallory Square, and eat at the Historic Seaport.
2. Day 2, on the water: a morning snorkel or charter trip on the reef, or a beach day at Fort Zachary Taylor. In the afternoon, visit the free Key West Garden Club at West Martello Tower or the Eco-Discovery Center, then end the night on Duval Street and at the Green Parrot Bar for live music.
3. Day 3, your choice: the full-day Dry Tortugas trip, or the Truman Little White House and the 19th-century Key West Cemetery, or a drive up to Bahia Honda, the Key Deer Refuge and the Turtle Hospital.

Where should you stay and eat?

Stay in or near Old Town if you can. Parking there is scarce and costly, while walking, bicycles and rideshares cover almost everything. Golf carts and scooters are popular to rent, but you rarely need one.

• The Casablanca Hotel: a 3-star historic boutique hotel on Duval Street in Old Town, about 4.5 km from the airport, with Victorian wraparound porches, a pool in tropical gardens and a breakfast cafe.
• Oceans Edge Key West Resort and Marina: on Stock Island, just outside Key West, with marina views, waterside paths and bike rentals, for a quieter base.
• What to eat: Key lime pie, best known at Blue Heaven for its tall meringue and at Kermit's Key West Key Lime Shoppe, frozen and dipped in chocolate on a stick; conch fritters and conch chowder; fresh snapper, mahi-mahi, grouper and spiny lobster; and Cuban food at El Siboney, away from the main tourist strip.
• Waterfront drinks: the Half Shell Raw Bar and Schooner Wharf Bar at the Historic Seaport, and Sloppy Joe's on Duval Street, with its Ernest Hemingway connections.

Common questions

What is the best month to visit Key West?

May is our pick for most trips, with late April close behind. May averages a high of 85.9°F and 3.12 inches of rain, the winter high season is over, and hurricane season does not start until 1 June. For the most comfortable weather regardless of cost, choose February or March, the driest months at about 1.5 inches of rain each.

What is the cheapest time to go to Key West?

Summer and early fall, from June to October, usually bring the lowest hotel rates, because the heat, afternoon storms and hurricane season keep many visitors away. Fantasy Fest week in late October is the exception. Key West is still one of Florida's most expensive places to stay, so expect high prices in any month, and book a refundable rate during hurricane season.

When is hurricane season in Key West?

Hurricane season in Key West runs from 1 June to 30 November, with the highest risk from August to October. September is also the wettest month, averaging 7.24 inches of rain. Monroe County can order visitors to leave the Keys ahead of a storm, so book refundable rooms and flights, and watch the forecast in the week before you travel.

What is the weather like in Key West in December, January and February?

Mild and mostly dry. Average highs are 77.7°F in December, 75.8°F in January and 77.4°F in February, with nights between 65.5°F and 68.3°F. Rain averages 1.54 to 2.16 inches a month. These are the most comfortable months for walking Old Town, which is why hotel rates and crowds are at their highest then.

When is Fantasy Fest in Key West?

Fantasy Fest is a 10-day costumed street carnival held every year in late October. In 2026 it ran from 16 to 25 October, and Old Town filled with crowds and partygoers. The event is aimed at adults. For a quiet trip, avoid that week; to go, book early and confirm the dates on the official Fantasy Fest website.

Is it better to fly into Key West or Miami?

Flying into Key West International (EYW) saves a long drive but usually costs more than flying into Miami (MIA). From Miami, the Overseas Highway drive takes about 3.5 to 4.5 hours in good conditions, and longer in traffic. For a short trip, we'd pay the extra for EYW. For a week, a cheaper Miami fare plus the drive often makes sense.

Is Key West expensive?

Yes. Key West is one of Florida's most expensive vacation spots, with hotel rates highest from winter to early spring. Flights into EYW are usually pricier than flights into mainland airports, and Old Town parking is scarce and costly. Walking, cycling and rideshares keep daily costs down, and the Mallory Square sunset and the West Martello garden are free.

How long is the drive from Miami to Key West?

About 3.5 to 4.5 hours in good conditions, and longer in heavy traffic. The route follows the Overseas Highway (U.S. 1) across a chain of islands and bridges, including the Seven Mile Bridge near Marathon. Good stops on the way include Bahia Honda State Park, the National Key Deer Refuge on Big Pine Key and the Turtle Hospital in Marathon.