GETAWAYS DESTINATION GUIDE
Key West Vacations
Pastel houses, sunset at the pier, and a drive down the Overseas Highway you'll be glad you didn't rush. Key West is a short flight and an entirely different pace.
Where to go in Key West
Old Town
Guesthouses, Duval Street, and the sunset celebration. Walkable, historic, and best for couples.
The resort side
Pools, marinas, and family space, a short ride from downtown.
The Middle Keys
Marathon and Islamorada. Snorkel trips, sandbars, and a slower stop on the way down.
When to visit Key West
December to April
Peak season. Perfect weather, book early for good guesthouses.
May and June
Warm water, long evenings, and better rates before summer heat sets in.
July to October
Hot and humid, and hurricane season. We always pair this window with travel protection.
November
A lovely quiet month with warm water and shoulder-season pricing.
Questions we hear most
Should we fly or drive?
Both work. Flying into Key West saves a day, driving from Miami is a gorgeous four hours if you stop along the way.
Is Key West good for families?
Yes, with the right hotel. We put families where there's a pool and space, and add snorkel or dolphin trips.
Can we visit on a cruise?
Often, yes. Several short Caribbean and Bahamas sailings stop here, and we'll plan the day so you're not rushed.
Let’s plan it together
Let's plan your Key West getaway
Tell us your dates, who's coming, and a budget range. We'll send real options with honest notes on each!