Holiday Events in Key West

Experience the perfect Key West holiday getaway with our collection of exceptional house rentals. Embrace the spirit of the season by requesting a beautifully decorated vacation rental that aligns with your holiday traditions. Each of our homes comes equipped with fully stocked kitchens, ensuring you have everything you need to prepare festive feasts and create cherished memories.

Believe it or not, Santa Claus does make his way to Key West, making it a magical destination to celebrate a tropical Christmas. Our dedicated vacation planners and our attentive Concierge Cindy are eagerly waiting to assist you in planning the holiday escape of your dreams.

Don't miss out on the opportunity to create treasured holiday moments in Key West. Explore our selection of house rentals today and let us help you craft a remarkable holiday experience that will be remembered for years to come.It's beginning to look a lot like Christmas in Key West! It's time for you to jingle our bells and reserve a premier vacation rental from our collection for your holiday celebrations with family and friends. We have intimate condos, luxury cottages, and larger homes that are just the right size for your guest lists. It doesn't matter if you've been naughty or nice — we just want you to come and enjoy our sand, surf, Santa and fun. Take a look at these holiday-themed events coming up in Key West and then let us help choose just the right vacation rental for you.

2020 Holiday Events in Key West

LIGHTING OF THE BIGHT: KEY WEST HARBOR WALK OF LIGHTS

November 25 TBD

**THE CITY COMMISSION IS STILL WORKING ON HOW TO EXECUTE THIS EVENT SAFELY - THIS EVENT IS 'TO BE DETERMINED' AS OF RIGHT NOW, DUE TO COVID 19 - STAY TUNED FOR MORE DETAILS** Gather on the Harbor Walk plaza at Greene and Elizabeth St. to best see the official lighting of the 2020 Key West “Harbor Walk of Lights” with more lights and creative displays than last year, all continuing the “Maritime History of Key West” theme! The Key West “Harbor Walk of Lights” traditional main features will light up that night, including the Fishing Buoy Tree, a fresh pine Nautical Christmas Tree and the original Key West Lobster Trap Tree. Harbor Walk of Lights, lit nightly through New Year’s Eve, stretches along the Key West Historic Seaport and Key West Bight Marina.

LIGHTING OF THE HOLIDAY TREE

November 30

**THE CITY COMMISSION IS STILL WORKING ON HOW TO EXECUTE THIS EVENT SAFELY - THIS EVENT IS 'TO BE DETERMINED' AS OF RIGHT NOW, DUE TO COVID 19 - STAY TUNED FOR MORE DETAILS**

KEY WEST LIGHTED BIKE RIDE

December 02

**THE CITY COMMISSION IS STILL WORKING ON HOW TO EXECUTE THIS EVENT SAFELY - THIS EVENT IS 'TO BE DETERMINED' AS OF RIGHT NOW, DUE TO COVID 19 - STAY TUNED FOR MORE DETAILS** Key West Lighted Bike Ride  The Key West Lighted Bike Ride is scheduled for Wednesday, December 2nd at Bayview Park.  Entry for the bike ride is an unwrapped toy or monetary donation for Holiday Helpers.  Wesley House Family Services coordinates this bike ride - registration begins October 1st at https://www.wesleyhouse.org/ This year the Coke Florida Caravan  will be in Bayview Park to provide free photos with Santa along with cookies (from Winn Dixie) and milk - 5pm – 7:30pm.  The Lighted Bike Ride will leave Bayview Park at 7pm Entry fee for the Bike Ride is one unwrapped toy for Holiday Helpers or monetary donation Claire at 305-809-5000 / Info@wesleyhouse.org  

December 3

It all begins with a Pre-Party Muster at the Southernmost Point Guest House (bring a snack to share and your drink of choice). We line up at 7:30; Parade rolls down Duval Street with our "Counter Intelligence Bar" at 8 PM and we're Keeping it Green - walk, push, peddle, or cruise in an electric cart - no automobiles please. But wait, it's not over until we dance at the Post Parade Awards Party!

CHRISTMAS PARADE

December 5

Key West will be showing its holiday spirit with the annual hometown parade with marching bands, groups and floats.  Route proceeds down Truman Ave to Duval, where it takes a right and continues on to Eaton Street.  Some streets will be closed for this event.

LIGHTING OF THE MENORAH

December 10

 **THE CITY COMMISSION IS STILL WORKING ON HOW TO EXECUTE THIS EVENT SAFELY - THIS EVENT IS 'TO BE DETERMINED' AS OF RIGHT NOW, DUE TO COVID 19 - STAY TUNED FOR MORE DETAILS** The community is invited to join us at Bayview Park for the traditional lighting of the menorah. Rabbi Shimon Dudai from Congregation B’Nai Zion and Rabbi Jacob Zucker from Chabad of the Florida Keys will say the blessings.

10TH ANNUAL SCHOONER WHARF BAR ANNUAL LIGHTED BOAT PARADE

December 12

December 26

The Key West Blues Festival has been postponed to Dec 26. This concert was originally set to take place on April 26, 2020. Tickets purchased for the originally scheduled show will be transferred to this new date and ticket holders will keep their same seats. Due to government mandates surrounding COVID-19, our box office is currently closed. As soon as we are able to reopen, all ticket holders will be notified directly via email with more details. Thank you for your patience and please stay safe and healthy! The Key West Blues Festival returns with Key West's blues performers to offer you an exclusive concert experience in its second year. You can look forward to seeing some of Key West's best blues musicians such as Bill Blue, Caffeine Carl, Ericson Holt, Michelle Dravis, Andy Westcott, Daryl Brooke, Joey Marchiano, Wayne Sorbellie, Francois Gehin, Henry Lysy Jr, Tom Conger, Randy Morrow, Bob Malone, Bobby Devito, R.B. Tolar, Tim Marshall Curtis and Rick Fusco! The Key West Blues Festival is brought to you by Joel Barrios (World Guitar Festival) and hosted by Bill Hoebee of iHeartRadio's “Hoebee in the Afternoon”. Venue Information: Key West Theater 512 Eaton Street Key West, FL, 33040  

December 29

**These are city-approved, physically distanced House Tours.  Masks will be required, of course, and hand sanitizers will be provided** The annual Key West Home Tours are one of the oldest and longest-running home tours in America, with the first tour in 1960. Old Island Restoration Foundation (OIRF) conducts the tours and they are funded in part by our generous supporters. Each tour features five lovely homes and gardens reflecting the varied tastes and originality of their owners.  You will be enchanted by exquisite restorations, creative renovations and delightful interiors featuring art collections, antiques, and much more. All proceeds from the tours stay in our local community fulfilling OIRF's mission of "Celebrating and sustaining Key West's unique architecture, culture and history." Grants are provided to local homeowners and non-profits to fix up their buildings in the historic district, scholarships are provided to Key West High School students and funds are used to maintain Key West Oldest House Museum and Garden. 

Start Planning your Holidays in Key West!

Experience the perfect Key West holiday getaway with our collection of exceptional house rentals. Embrace the spirit of the season by requesting a beautifully decorated Key West vacation rental that aligns with your holiday traditions. Each of our homes comes equipped with fully stocked kitchens, ensuring you have everything you need to prepare festive feasts and create cherished memories.

Believe it or not, Santa Claus does make his way to Key West, making it a magical destination to celebrate a tropical Christmas. Our dedicated vacation planners and our attentive Concierge Cindy are eagerly waiting to assist you in planning the holiday escape of your dreams.

Don't miss out on the opportunity to create treasured holiday moments in Key West. Explore our selection of Key West house rentals today and let us help you craft a remarkable holiday experience that will be remembered for years to come.