Discover the captivating and charming visuals of vintage tropical Christmas photos from the 1920s to the 1960s.

From Florida to Hawaii, these snapshots of Yuletide cheer serve as a precious glimpse into a festive season that combined island living with holiday merriment. Explore the unique and nostalgic moments captured in these treasured photographs, some of which may even have been taken by your own grandparents!

A special article that will reignite your passion for the holiday season!

Vintage Tropical Christmas Photos

1920s – 1960s

1950s vintage photo of 2 women in 1950s swimsuits having a christmas party on Bondi Beach, Sydney Australia 1959.

Source: Art Blart

1960s photo of Santa in the Ala Moana Mall parking lot in Honolulu, Hawaii. Is Santa holding seashells?

Source: Pinterest

In 1958, Liberace’s Deep Well Estate home was chosen by the Palm Springs Villager magazine as the Home-of-the-Month for December.

His home included a large fireplace that dominated the black and white living room. That year, during the holidays, the entire living room was transformed into a winter wonderland with trees, snowmen and icicles hanging on eaves overlooking the pool (Source).

Source: Palm Springs Life

Want to enjoy your Christmas Tree while hanging out by the pool? Why not add it INSIDE the pool? 1957 Vintage Photo.

Source: Pinterest

Christmas Music Guidebook: A Hawaiian Holiday Hullabaloo (Hawaiian Holiday albums)

Excerpt: “The concept of Christmas carols with an island twist might seem a bit incongruous at first glance, but these two disparate flavors have combined for some hugely memorable music.  The Andrews Sisters set the standard for South Seas caroling when they released Christmas Island in 1946, and repeated the trick a few years later in 1949, when they convinced Bing Crosby to stop longing for a “White Christmas” long enough to make Mele Kalikimaka part of the national vocabulary.

Still, it wasn’t until the late ’50s that this combination reached full bloom.  Hawaii’s ascension to statehood in the late 1950s, the rise of Tiki culture, and the national surfing craze that followed the release of the Gidget novel and movie sparked a rush of Polynesian-themed product – inevitably, Christmas albums followed.“

Source: Depth of Field

Christmas on a Southern California beach in the 1930s.

Source: Pinterest

1950s photo of a couple sunbathing by the sea at Palm Beach, Florida, circa 1955 by Slim Aarons.

Source: Pinterest

Santa (in his shorts) and swimmers on the beach, Los Angeles 1927.

Source: Gray Flannel Suit

1954 vintage photo of Santa Claus water skiing with a female friend in her cute holiday themed swimsuit.

Source: 1000museums.com

1950s photo of Santa on a boat.

Source: Fans in a flashbulb

Question time: Do you live somewhere warm (or travelled / travels to a warm destinations) and celebrate Christmas? Share what you do to bring a winter feeling to your holiday in the comments section below.

Last but not least I wanted to showoff some of my Christmas looks for all the fun events I was able to squeeze in before Omicron hit. My fav was Mr & Mrs. Claus with my husband (he is wearing my grandfathers suit from the 1970s). I am also very proud of my “Tree-ara” that I made out of bottle brush trees, cotton balls and a vintage deer I have had for years. So fun!

Merry Christmas & Happy Holidays friends!

Further Reading: Vintage Christmas Blog Posts from the 1920s-1960s

Liz