Tis The Season In Key West

key west at christmas

The holiday season is upon us, and Key West invites you to share in our festive celebrations. The season kicks off on Wednesday, November 24th at 5 p.m. with the Lighting of the Harbor Walk of Lights at the Historic Seaport.   The first Monday after Thanksgiving, November 29th, the City will hold the Tree Lighting ceremony at 6 p.m. at Bayview Park. Always a family favorite, this ceremony will feature the Horace O’Bryant School Jazz Band, and culminate with the arrival of Santa.   The next evening, at 5:30 p.m. on November 30th, Rabbis Shimon Dudai and Jacob Zucker will perform the Lighting of the Menorah at Bayview Park.   Finally, the Holiday Parade will be held on December 4th beginning at 7 p.m. The parade begins at the corner of Truman Ave. and White St., proceeds to Duval, then to Eaton St.   “It is so heart warming to see the community coming back to normal,” said City Manager Patti McLauchlin. “These hometown traditions are part of what makes Key West magical.”   Historic Key West Vacation Rentals has these magical conch style homes and cottages available for your yuletide getaways. Reserve yours right on our website or with our equally festive Vacation Planners by calling 305.296.1010 or by emailing bookings@historickw.com.

Butterfly Cottage - - NEW Nightly Rental 2 Bedrooms 2 Bath Sleeps 4

This home has been totally "reborn"! New plumbing, central air conditioning, updated appliances in brand new kitchen, and new flooring throughout the home. Televisions are in each bedroom and one in the main room. Great WIFI for working, schooling or just browsing!

Casablanca Too - Nightly Rental 1 Bedroom 1 Bath Sleeps 2

This is a spacious one-bedroom vacation rental with the added bonus of off-street parking, in-wall A/C, and a private hot tub! 

Chick-a-Pea Cottage - Nightly Rental 4 Bedrooms 2.5 Bath Sleeps 8

Chick-A-Pea is a traditional Key West cottage that has undergone a complete renovation. The charm and historic features have been retained, while all the luxuries of today have been added, including an amazing little private pool!

Harry Truman Suite - Nightly Rental 2 Bedrooms 1 Bath Sleeps 5

The Harry Truman Suite is on the first floor, in the front of the building. The property is ideally located only a half block to Duval Street. It is also close to many attractions and walkable to the Lighthouse, Southernmost Point, the Hemingway Home and many shops, restaurants, and galleries. 

Margaret Truman Suite - Nightly Rental 2 Bedrooms 1 Bath Sleeps 5

Located in Old Town, between Duval and Whitehead Streets. Enjoy the many tourist attractions located close by as well as numerous restaurants, shops, and galleries. 

Martha Truman Suite - Nightly Rental 1 Bedroom 1 Bath Sleeps 3

You’re close to everything Key West and Duval Street, and you’re just around the corner from the Ernest Hemingway Home and Museum.

Villa Josine - Nightly Rental 4 Bedrooms 4.5 Bath Sleeps 8

 Villa Josine is an amazingly beautiful home located in one of the most sought after locations in Key West. The open-concept living and dining area is the perfect place for friends and family to gather together and relax in unmatched comfort.

Villa Luxe - Nightly Rental 3 Bedrooms 3.5 Bath Sleeps 7

VILLA LUXE reveals a discreet but sexy glamour beyond its gates––and it’s no wonder, since it was once owned by a hip clothing brand.

Serene Lily - NEW Weekly Rental 2 Bedrooms 2.5 Bath Sleeps 6

Located where the Gulf meets the Atlantic, this home is perfect for two couples or a small family. Its open concept first floor is flooded with natural light. 

Galveston Getaway- NEW Monthly Rental 3 Bedrooms 2 Bath Sleeps 6

 Enjoy your morning coffee on the covered front porch. Or relax in the hot tub near the furnished paver patio out back.

My Happy Place - Monthly Rental 2 Bedrooms 2 Bath Sleeps 4

 From its delightful mosaic-tiled, covered front porch to its back yard dip pool, this Key West home will surprise you! Petite yet grand, this home is walkable to many attractions.

Poppy Cottage - Monthly Rental 1 Bedroom 1 Bath Sleeps 2

Picture “perfectly adorable” and you have Poppy Cottage, an absolutely delightful Key West vacation rental. The Old Town property was recently renovated and updated to its owner’s discerning standards. The home is light-filled and supremely private.

We really do wish you a very merry Christmas. We'd just rather do it in person, so come on down. Key West is in a festive mood and you will be, too!