Best Time to Visit Key West
- Blog
- 09/08/2025
- BLUE FLAMINGO GUIDE
Key West Weather, Crowds & Events by Season
If you’re dreaming of turquoise water, tropical cocktails, and days that end with sunset over the sea, Key West should be at the top of your list. But when’s the best time to go? Whether you’re chasing warm winter sun, looking to avoid crowds, or planning around events, this guide breaks down what to expect—season by season.
PEAK SEASON PERFECTION
Winter (December – February)
Weather: 70s–80s and sunny
Crowds: High
Why Go: Escape the cold, holiday charm, outdoor everything
Winter is Key West at its most iconic. With perfect temps and zero humidity, this is the time to dive into water sports, al fresco dining, and beach lounging. But with gorgeous weather comes high demand—expect more crowds and higher hotel rates.
Top Events:
- New Year’s Eve Conch Shell Drop
- Key West Food & Wine Festival (January)
- Valentine’s Getaways & Winter Sun Escapes
Insider Tip: Book early (especially for the holidays) and secure your poolside cabana at Blue Flamingo in advance.
WARM DAYS & LOCAL VIBES
Spring (March – May)
Weather: 75–85°F
Crowds: Moderate to High
Why Go: Spring Break energy, outdoor events, ideal beach weather
March brings Spring Breakers, but by April and May, the vibe mellows out. It’s one of the best times to enjoy Key West’s beaches and bar scene without the summer humidity. Blue Flamingo’s pool scene hits its stride—think live DJs, lawn games, and bottomless brunches under the sun.
Top Events:
- Conch Republic Independence Celebration (April)
- Songwriters Festival (May)
- Easter & Mother’s Day Getaways
HOT, SUNNY & EASYGOING
Summer (June – August)
Weather: Upper 80s–90s with humidity
Crowds: Low to Moderate
Why Go: Best hotel deals, family vacations, warm ocean temps
Summer in Key West is hot—but with fewer tourists, it’s a great time for spontaneous escapes, lower rates, and a slower pace. Snorkel trips, jet ski tours, and quiet beach days are all in play. It’s also a favorite time for families and group trips.
Top Events:
- Key Lime Festival (July)
- Fourth of July Celebrations
- Hemingway Days (July)
Stay Cool Tip: Book a cabana at Blue Flamingo with a mini fridge and fan. Then hop between the two pools with a frozen drink in hand.
QUEIT ESCAPE & QUIRKY FUN
Fall (September – November)
Weather: 75–85°F, occasional rain
Crowds: Low
Why Go: Cheapest rates, local experiences, festive fall events
Fall is Key West’s secret season—less crowded, more relaxed, and full of funky local festivals. It’s also hurricane season, but storms are often brief and the deals are unbeatable. For travelers looking to unwind without the bustle, this is your window.
Top Events:
- Womenfest (September)
- Fantasy Fest (October) – Key West’s most outrageous party
- Parrot Heads in Paradise (November)
Note: Keep an eye on weather forecasts, and snag last-minute deals at Blue Flamingo if you’re flexible.
So, When Is the Best Time to Visit Key West?
It depends on your vibe:
| If you want… | Go in… |
| Perfect weather & peak energy | Winter |
| Fewer crowds & spring festivals | Spring |
| Best value & warmest water | Summer |
| Local charm & funky events | Fall |
Where to Stay
No matter the season, Blue Flamingo Resort offers a laid-back home base with everything you need: two pools, luxe cabanas, on-site bars, and a playful energy that feels distinctly Key West (without the Old Town crowds).
Book your stay today—and experience Key West in season, your way.
