Whether you visit in summer, fall, winter, or spring, you’ll always discover a reason to fall in love with life in Key West.
Spring: Festivals, flowers, and fresh flavors
Spring brings Key West into full bloom. March and April are made for biking through Old Town, meandering through mangrove forests, or snorkeling at Dry Tortugas National Park. It’s also the start of event season, beginning with the locally loved Conch Republic Independence Celebration, scheduled for April 17, 2026.
Summer: Warm seas and easy days
Yes, it’s warm, but that’s exactly why the summer season is a local favorite. The crowds thin, the ocean is like a tropical bath, and life slows to an irresistibly tranquil pace. Think sunset paddle boarding, lobster dives, and outdoor dining under the stars, either in one of the island’s world-famous restaurants or in the privacy of your own Historic Key West Vacation Rentals accommodation. Don’t miss beloved annual events, like the famous Key Lime Festival (love and limes!), billed as America’s favorite citrus celebration, in early summer (July 1, 2026). To make summer even more inviting, Historic Key West Vacation Rentals offers special seasonal rates on many of our monthly stays, so it’s the ideal time for an extended getaway. Or consider a remote-work escape, where you’ll conduct business as usual in flip-flops from the serenity of your private patio with shady lush tropical landscaping.
Fall: Quiet, cool, and colorful
By the time autumn arrives, the island settles into a slower rhythm, a match for travelers who crave peace, space, and lower rates. Enjoy long walks along the harbor or peruse Key West’s incredible plethora of art galleries. You won’t want to miss the spirited Fantasy Fest, the island’s most colorful celebration, October 2026, when a 10-day party rolls into town and transforms the streets of Old Town.
Winter: Classic paradise
Of course, winter remains a dream. While the rest of the country cools down, Key West exudes sunshine, lively street music, and the energy of happy visitors escaping the cold. It’s also prime time for outdoor dining, sunset sails, and fabulous waterfront strolls. Don’t forget to avail yourself of our Historic Key West Vacation Rentals Concierge Services, who stand at the ready to assist you in arranging excursions, reservations, transportation, charters, day trips, and much, much more. These local experts offer friendly advice and even complete itinerary planning for your stay in Key West.