Experience The Holidays Island Style in Key West

No matter what time of year it is, you can have a great time experiencing different aspects of each season when you stay in Key West, FL. There are lots of festivals in Key West that celebrate different aspects of the year each month. Along with these festivals, it can be a fun time for the whole family to spend different seasons experiencing the area in one of the best rentals in Key West. When the holiday season rolls around, Key West can be the best place to spend the holidays in style!

With fun activities for the whole family to enjoy along with amazing restaurants for you to visit, you can spend the holidays in Key West and discover what all the hype is about for yourself.

Festive Fun

Key West has many different activities that you can participate in during the holiday season. Spending Christmas in Key West can be one of the best vacation experiences you have during the winter season.

From the Harbor Walk of Lights to the Annual Rudolph Red Nose 5K Run, there is something for everyone to enjoy when you spend Christmas in Key West. You can even take some time and enjoy the Key West holiday parade.

Harbor Walk of Lights

A great way to kick the Christmas season off in style is by attending the lighting of the Harbor Walk of Lights. The lighting of the Harbor Walk of Lights is typically held near the end of November and serves as the start of the Christmas season. While attending the lighting of the lights is a joyful experience, you can also have a great time at the Harbor Walk of Lights anytime after the lighting.

The Harbor Walk of Lights is perfect for those who enjoy observing beautiful Christmas lights. The traditional main features of the Harbor Walk of Lights are truly a sight to behold. There are also many different shops that you can visit while experiencing the Walk of Lights.

Old Town Trolley’s Holiday Lights Tour

If you enjoy viewing the beautiful lights that come with the holiday season, you should also take a visit to the Old Town Trolley’s Holiday Lights Tour. 

While taking a ride on the Old Town Trolley’s Holiday Lights Tour, you can kick back island-style and observe the historic Key West homes that the locals have decorated for the holiday season.

The holiday lights tour is one of the best experiences you can find in Key West during the holiday season, and the narrators of the tours are very insightful with the information that is given on the tour. It is perfect for holiday-light viewers and new visitors alike.

two people wearing santa hats on the beach
Photo from Shutterstock

Schooner Wharf Bar Tree Trimming Party

The Schooner Wharf Bar Tree Trimming Party is a celebration for the locals of Key West along with any holiday visitors. This is truly a tradition that helps to bring the community together.

At the Schooner Wharf Bar Tree Trimming Party, you can add a piece of yourself to the community by adding your ornament to hang on the 8-foot tall Christmas tree. The handmade ornaments you bring can be entered into contests that are held at the event, and you can win some amazing prizes.

Annual Rudolph Red Nose 5K Run

The Rudolph Red Nose 5K Run is held every year by A Positive Step of Monroe County. This non-profit organization has been serving the high-risk kids of Monroe County as well as their families since 1999.

The run is held in December, and it is a fun event for everyone who participates. You can run in the 5K or be a spectator and cheer on the runners. 

Track Santa Over the Keys

Another event that is a great one for the entire family is Track Santa Over the Keys. This is done on Christmas Eve.

This event is meant to bring excitement for Christmas Eve night, as everyone watches to see where Santa is on his journey around the world delivering presents to all the good children.

Restaurants

You can also enjoy some delicious food at some of the restaurants in Key West during your holiday stay.

Seven Fish

If you are looking for a classic place to dine in Key West, you should visit Seven Fish. Seven Fish has been serving delicious, fresh local fish in a contemporary bistro setting for approximately 20 years.

Around the holidays, Seven Fish has a holiday menu that you can order from. This menu is $99 per person, and the meal consists of three courses that you can choose from. You can choose a starter, an entree, and a dessert for this menu price. It is the perfect holiday meal for a good price.

Four Marlins

If you want to enjoy some nice oceanfront dining, you should make a stop at the Four Marlins. The design of the Four Marlins is based on the tropical fishing lodges that were around in the 1930s.

You can get up early and enjoy a delicious breakfast, have brunch on the weekends while listening to some live music, or come by and enjoy some classic comforts for lunch or dinner. You are guaranteed to have some amazing food and a cozy experience when you dine at the Four Marlins.

Tavern n Town

If you want something good to eat but want more than seafood and ocean decor, you can visit the Tavern n Town. The Tavern n Town is quickly becoming one of the most popular restaurants in Key West.

The Tavern n Town is where luxurious surroundings and life’s simple pleasures come together in harmony. The Tavern n Town also has a menu with a wide variety of meals that you can choose from. Whether you want seafood or if you want a nice, big steak, you can find it at Tavern n Town.

Plan Your Visit

Ready to experience the holidays in style? Book your Key West rentals with Historic Hideaways today and create a magical experience for the whole family!

Large Rentals for the Whole Family

The holidays are made better when the entire family can be together. For this reason, you want to make sure you book a rental large enough for everyone. Luckily, there are some large rentals that you can rent in Key West that are perfect for the whole family.

Truman House

With four bedrooms and three full bathrooms, the Truman House has enough room to house at least six people. With street parking, a private heated pool, internet access, and cable television, the Truman House can be the perfect place for you to rent to spend the holidays in Key West with your entire family.

Paradise Grand

Paradise Grand is another large Key West house rental that you can book for your stay during the holidays. With five bedrooms and four bathrooms, Paradise Grand can house ten people comfortably.

Paradise Grand has off-street parking and is within biking distance of the beach. It is the perfect place for your family to stay when spending the holidays in Key West.

Sea Stone

Another great Key West house rental that is perfect for large families is Sea Stone. Sea Stone is a four-bedroom and four-bathroom house that can sleep eight people comfortably. It is within walking distance of the beach and has central heating/cooling as well as a private heated pool.

Book Your Key West Vacation Rental With Historic Hideaways

Key West can be a great place to spend the holidays. Historic Hideaways has many Key West house rentals perfect for you and your family. Historic Hideaways also has Key West monthly vacation rentals that are the perfect option for an extended stay in the beautiful Florida Keys.