With a trip to Key West, you can enjoy sun-drenched days filled with boating and swimming, as well as evenings featuring fresh seafood and margaritas. With warm temperatures throughout the year, this town is a prominent getaway destination. Located on the last of the Florida Keys, Key West is the southernmost point of the United States. The Key beckons visitors to spend days on the beach, as well as partake in snorkeling, biking, and scuba diving. Booking a Key West vacation rental means you can stay close to noteworthy attractions like the Ernest Hemingway Home and Museum. Deciding on the best time to visit Key West and what to pack is a matter of knowing what each season has to offer.

Visiting Key West in the Summer

Summer in Key West brings the hottest weather of the year, with temperatures soaring into the lower 90s in July and the upper 80s in June and August. This makes for the perfect weather to indulge in swimming, snorkeling, and boating, and the light breeze off the ocean and almost daily afternoon showers help to keep you cool. In the evenings, temperatures fall slightly into the 70s, making it the perfect weather for dinner on the patio of Blue Heaven. Include lots of sunscreen on your packing list, along with shorts, flip-flops, and light linen shirts.

Stay cool with a ride on the Old Town Trolley, which stops at the major attractions. Enjoy the air conditioning and avoid afternoon showers on a tour of Ernest Hemingway Home and the Harry S. Truman Little White House. Since 1964, the Key West Fishing Tournament is one of the best-known fishing tournaments in the area, and you can watch the festivities or sign up to cast your own line. As the sun begins to dip, make your way from your vacation rental to Mallory Square to see the street performers, and grab a beer and conch fritters from one of the food trucks and vendors around the square.

Find the perfect Key West vacation rental on Tripping.com. Tripping.com is the world's #1 vacation rental search engine with over 10 million properties!

Visiting Key West in the Fall

Kids return to school, families vacate the Keys, and the temperatures cool a little as fall arrives in Key West. Starting in September, the daily highs remain in the high 80s but gradually fall to the low 80s by the end of November. You definitely need an umbrella in September, as it’s the rainiest month of the year. Evenings bring some relief from the heat, but the temperatures still remain in the mid to low 70s.

If you love Jimmy Buffett, then plan to arrive in Key West in early October for the Parrot Heads Meeting of the Minds event. You can enjoy a few day of enjoy live music and entertainment, and attend talks by like-minded Parrot Heads. Get some thrills and chills just in time for Halloween with the Ghosts and Gravestones tour on the Trolley of the Doomed. The trolley takes visitors to all the most haunted sights on the island and regales them with tales of ghosts and voodoo. In the evenings, stop by the Hogfish Bar and Grill or Louie’s Backyard for a dinner of seafood and views of perfect sunsets along the beach.

Visiting Key West in the Winter

In the winter, visitors flock to Key West to get a good dose of sunshine before returning to their cold, snowy hometowns. Although temperatures are mild in the mid-70s, you want to pack a bathing suit for swimming in the warm waters of the Gulf of Mexico. In the evenings, the cool ocean breeze and temperatures in the mid-60s call for a light sweater or jacket. Pack light cotton pants and layers of short- and long-sleeved tops for walking or biking around the island during the day.

As the holidays approach, the town comes alive in a riot of holiday lights and decorations. See the best light displays from the Holly Jolly Holiday Trolley, which spends around an hour showing you the best-decorated homes and businesses in town. Take a stroll along the marina to enjoy the Lighted Boat Parade in mid-December. The town also holds a parade each year. On New Year’s Eve, Duval Street is the place to be to watch the annual Conch Shell Drop. In February, put on your dancing shoes and attend the Mile 0 Fest at the Truman Waterfront Park Amphitheater.

Visiting Key West in the Spring

Springtime brings warmer weather without being too hot or humid. Temperatures hover in the low 80s during the day and mid-70s after the sun goes down. When packing, you need to add a rain jacket to the list for the frequent showers. Fill the rest of your suitcase with plenty of sunscreen to work on your pre-summer tan.

At the Taste of Key West festival, local restaurants and wineries show up at Truman Waterfront Pier with samples from their menu. Wander around the area indulging in the best food the island has to offer before choosing a place to eat during your trip. Start practicing now for the annual Conch Shell Blowing Contest in March. It’s free to enter, and everyone is welcome to take their shot at the Conch Honk. Peek inside some of the older homes during the Key West Home Tours in March.

When Is The Best Time To Visit Key West?

Many factors go into deciding the best time of year to visit Key West, and you can’t really go wrong visiting during any season. However, the spring seems to have a small advantage over other times of the year. The warm weather isn’t too hot, but it’s still warm enough to spend days swimming and snorkeling. The flowers bloom throughout the island. The best part is the Taste of Key West, which lets you eat your way through some of the best restaurants in town a couple of bites at a time.

Ready to go? Check out these amazing Key West vacation rentals on Tripping.com.