December in Key West: Book ahead for a holiday in paradise

Warm-weather holiday fun

In December, Key West beckons with balmy breezes, offering the ideal escape from the winter chill. Average daytime temperatures hover in the mid-70s to low 80s, while evenings dip comfortably into the mid-60s — making strolling through festive light displays or enjoying meals outdoors a dream. With warm sunshine, gentle trade winds, and little rain in sight, the island creates a holiday backdrop unlike anywhere else: palm trees wrapped in twinkling lights, sparkling tropical waters, and plenty of opportunities to celebrate the holidays in flip-flops. Beyond official festivities, families can create their own tropical holiday memories:

• Beach day in December: Build a sandcastle (or holiday village) or go for a swim. Don’t forget your snorkel!
• Biking through Old Town: Ride past conch cottages decorated with wreaths, palm trees strung with lights, and quirky island-style holiday displays.
• Sunset Celebration at Mallory Square: Every evening in Key West feels like a festival, but during Christmas week, street performers and artists add some holiday sparkle against the backdrop of a magnificent island sunset.
• Holiday dining: Indulge in fresh seafood or island takes on holiday classics at local restaurants, many of which offer special menus. Or simply gather in one of our fabulous homes, where you’ll find a gourmet kitchen to prepare your own holiday meal to remember.

Why book ahead?

Key West is one of the most popular destinations for holiday vacations, and with good reason. Rentals fill up quickly as families from colder climates seek sunshine and celebration. Booking now ensures you’ll have your pick of our most charming historic homes — whether it’s a cozy cottage for two or a spacious retreat with room for an extended family. At Historic Key West Vacation Rentals, you can always look forward to the following amenities:

• Fully equipped kitchens for preparing your special family holiday feast
• Private pools and lush tropical outdoor spaces
• Walkable access to bars, shops, restaurants, and holiday celebrations
• The unique charm of historic homes with modern comforts

Give your family the gift of a holiday in Key West! Check out two of our favorite vacation rentals available during Christmas season, guaranteed to provide your family with a holiday to remember: 

• Chavez House: This charming 3BR, 2BA traditional eyebrow house accommodates up to six guests, with a completely updated kitchen and an emphasis on island-style living with a private pool and gorgeous lanai. You’ll be close to many of Key West’s most popular attractions, restaurants, and shops in this Old Town location.
• Fair Winds at the Foundry: Settle in with the family in this 2BR, 2.5BA end-unit townhouse tucked inside the exclusive Truman Annex. You’ll enjoy a lush tropical courtyard and spacious outdoor dining area, and you’ll be within walking distance of Mallory Square and the Truman Waterfront Park. Vaulted ceilings and an abundance of windows flood this three-level home with island sunlight.

Make December one to remember

Instead of shoveling snow, imagine sipping a Key lime martini by the pool while palm trees twinkle with holiday lights. Picture waking up every morning to a promising day of making tropical memories under the Florida sun. December in Key West isn’t just a vacation — it’s an experience filled with joy, creativity, and the kind of holiday cheer you and your family will never forget.

Book your holiday stay today

Our holiday homes fill up quickly — reserve your family’s festive getaway with Historic Key West Vacation Rentals now, and unwrap the gift of sunshine, celebration, and island magic this holiday season.