Tag Archives: Christmas

Christmas in Key West Shines Merry and Bright

Christmas in the Florida Keys is nothing short of magical. The lack of a single snowflake is more than made up for by the endless grains of powder-soft sand that you can sink your bare toes into during a stroll along our white sand terraces and pretty palm-lined paths. Key West is a particularly popular destination during the holidays, so book your Christmas vacation of a lifetime early, to avoid missing out on a spectacular festive experience. Book in advance to save more on Christmas vacations in Key West!


During the holiday season, the island’s palm trees are illuminated with lights, conch cottages are decorated with colorful holiday displays and sail boats are magically lit up on the waterfront. From fun events and entertaining activities to spacious, luxury accommodations, here are just some of reasons to visit Key West during the Christmas holidays.

Christmas in Key West


Wake up to water or garden views in spacious luxury villas

At Parrot Key Resort, space is never compromised so you will enjoy sprawling out in style in one of our three-bedroom villas. Ideal for families and groups of friends, you can unwrap gifts, play games and unwind together in the exclusivity of your own villa which overlooks stunning views of either the sparkling waters of Florida Bay or our tropical gardens.


Your spacious villa includes a third floor bedroom with two twin beds, a master bedroom with a king bed, and a ground floor guestroom with a double queen bed–perfect for accommodating up to 8 guests. Other bed type combinations are available to request upon booking.

Festive dining with a Florida Keys tropical twist

You will be spoiled for choice when deciding where to dine with family and friends, and the key to creating a memorable, happy occasion for festive indulgence is to book early. There are delicious menus and holiday specials available at many well-established restaurants across Key West. For inspiration on where to dine, visit hereCafé Blue at Parrot Key Resort is open throughout the holidays to bring you refreshing snacks and celebratory Christmas cocktails during your poolside relaxation.


Kick back and relax under the winter sunshine

During the depths of winter when it’s usually grey and cold in many parts of the world, Key West is a haven of natural beauty, adventure and quirky culture waiting to be explored under a subtropical sunshine. What a treat waking up on Christmas Day morning to soak up the scenery of tropical gardens or the calm ocean before taking a dip in one of our four heated pools, each nestled in its own lush oasis. This is where you can really switch off from the usual Christmas chores that come with preparing and then clearing up a mammoth meal.


Key West Christmas Events

  • December 3  – 20, 2015: Key West Holiday Fest- Each year a wide range of seasonal celebrations takes place throughout Key West. Events include the lighting of the Harbor Walk of Lights, tours of historic decorated inns, a holiday parade and much more.
  • December 3 – 6, 2015: Hot Pink Holidays- Sponsored by the Key West Business Guild, this LGBT holiday event is full of of festive activities as well as special retail opportunities on the island. Events include “flash mob shopping sprees” for gifts galore, holiday lights tours, a hometown holiday parade experience and Christmas caroling.
  • December 5: Key West Holiday Parade- The island city shows its holiday spirit with this annual hometown parade. Featuring marching groups and motorized and non-motorized floats, the festive procession traditionally draws entries from churches, civic organizations, businesses and neighborhood and school groups. The route includes Truman Avenue and White Street and then proceeds down Truman to Duval, where it takes a right and continues on to Eaton Street. Contact: 305-809-3881.
  • December 12, 2015: 25th Annual Key West Lighted Boat Parade- Vessels of every size and shape deck their hulls and light up the night with creative displays. Visitors in recent years have enjoyed a Keys-style twist to the usual winter wonderland displays, including a Santa’s sleigh guided by dolphins rather than cold-weather reindeer. Festivities start at 6 p.m. and the parade begins at 8 p.m. Boats will come into the Key West Bight and pass in front of the judges’ stand at Schooner Wharf where live music will be played all evening to add to the holiday spirit.
  • December 12: Schooner Wharf Bar Annual Lighted Boat Parade- Lighted and decorated vessels from rowboats to tall ships proceed around Key West’s Historic Seaport and harbor areas. Parade is scheduled to begin at 8 p.m. Holiday revelers can watch and applaud from bars, restaurants and resorts in and around the Historic Seaport. Contact: 305-292-3302.
  • December 20: Monthly Artisan Market — Holiday/Shop Local- The Key West Artisan Market is a vibrant, open air bazaar filled with artists, authors, chef-made cuisine, craftspeople, performers, fresh produce, baked goods, cheeses and flowers, craft beer & wine from residents representing the diversity of creativity, ingenuity and locally made products of the Keys & Key West. Held the first Sunday of the month, during season (thru April) outdoors at the Restaurant Store, 1111 Eaton. Free family & pet friendly event. Email: jill@dailyplan-it.net.
  • December 31, 2015: Key West New Year’s Eve- Celebrations include the lowering of the Conch Shell over Sloppy Joe’s on lower Duval Street, the lowering of famous Key West drag queen Sushi (riding a huge high-heeled shoe) over the Bourbon Street Complex on upper Duval Street, and the lowering of the “pirate wench” from the mast of a schooner in the Historic Seaport. Expect everything out of the ordinary during New Year’s Eve celebrations in Key West.

Call 855-327-7200 to speak with an onsite vacation planner or book reservations online now.


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Lit boat parade

Here are a few photos from the Lit Boat parade this past weekend, one of many fantastic Key West christmas events.

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Upcoming Holiday Performances

Check out these Christmas performances in Key West!

  • Fantazimo- 4th annual Holiday Burlesque show at The Studios Key West. Get more info Here.
  • Black, White and Twinkle Lights-  An evening of Live music and dance at the Tennesee Williams Theatre.  Hors d’oeurves, champaign and salsa music with silent auction to benefit the theatre. For tickets, click here.
  • Key West Theatre “holiday”- Child friendly holiday dance performance at the San Carlos Institute, featuring a cameo by the children of the FKCC ballet program.  For tickets, click here.
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