Mojitos Pool Bar
Cuban-inspired cocktails served poolside, with a mojito ready for every holiday toast.
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Key West Christmas & Holiday Events
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Stay up-to-date on everything happening at Havana Cabana, Key West's newest hotel.
December
Christmas in Key West at Havana Cabana
Christmas in Key West means warm days, palm trees in place of pine and a slower pace than the season back home. Spend the morning by the largest pool in Key West, take the shuttle to the Historic Seaport for an evening among the lights and come back for a nightcap at the resort. Our restaurants and bars stay open on Christmas Day, and our concierge can help with dinner reservations and local plans.
For a Christmas getaway for two, the Luis Premium King Balcony has a king bed, a sitting area and a balcony made for Christmas morning coffee. Friends and families sharing a room can choose the Luis Premium Two Queens Balcony, or the Havana Two Queens Poolside with its patio and pool views.
December
Key West Lighted Boat Parade
Decorated boats of every size sail through Key West Bight during the annual Schooner Wharf Lighted Boat Parade, one of the island’s best-loved December events. The 2026 parade sails on Saturday, December 12 at 8pm, with steel band music along the Harbor Walk from 6pm.
Take the hotel shuttle to the Historic Seaport, find a spot on the docks and stay for dinner by the water.
Harbor Walk of Lights
Over the holidays, the Historic Seaport’s Harbor Walk is lit up for an evening stroll along the water. Pair it with dinner or drinks at the Seaport, then catch the shuttle back to Havana Cabana. Shuttles run every half hour.
December
New Year’s Eve in Key West
Ring in the new year somewhere warm. Key West’s New Year’s Eve celebrations fill Old Town with music and countdowns, while Havana Cabana gives you a pool, a mojito and an easy first morning of the year. Book early, as the island fills up over the holiday week.
November
Thanksgiving Weekend in Key West
Turn the long weekend into a warm-weather trip. Thanksgiving falls on November 26 in 2026, giving you four days of pool time, island exploring and Cuban-inspired food and drink at the resort.
More Key West Events Through the Year
There’s something happening in Key West all year round. Click through the months to plan your next trip around a festival, race or island celebration.
January
Key West Half Marathon
Lace up for the annual Key West Half Marathon, a scenic island course that draws runners from across the country.
January
Key West Seafood Festival
A family-friendly celebration of local seafood and the Keys’ commercial fishing industry, with live music, drinks and local crafts.
February
Mile 0 Fest
Four days of Red Dirt and Americana music at the oceanfront Truman Waterfront Park Amphitheater.
February
Big Game Parties
Why just watch the game when you can experience it Flama Cabana-style? Grab your team for game-day eats and the big game on the big screen.
March
NAS Key West Southernmost Air Spectacular
Watch spectacular aerial maneuvers at Naval Air Station Key West, with free admission to the show.
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April
Seven Mile Bridge Run
Held every year since 1982, the Seven Mile Bridge Run brings runners from around the world, with proceeds supporting local schools and youth groups.
May
Key West Songwriters Festival
For over 20 years, the festival has brought top songwriting talent to Key West, with more than 50 shows across five days.
June
Key West Pride Fest
Each year the island celebrates PRIDE week, honoring Key West’s open and accepting spirit and the progress of the LGBTQ+ community.
July
Hemingway Days
Every July around Ernest Hemingway’s birthday, admirers celebrate his legacy with readings, tournaments and a lookalike contest.
August
Lobster Fest
Celebrate the start of lobster season with a bar crawl on Duval, a lobster boil, a street fair and Sunday brunch.
September
Key West Women Fest
Women from around the world come together for a week of parties, nightly events and food and drink specials.
October
Fantasy Fest
Started by locals in 1979, Fantasy Fest brings 10 days of costumes, parades and celebration to Key West every October.
November
Power Boat World Championship
The Key West World Championship closes the Super Boat International offshore racing series with a week of racing at the Truman Waterfront.
Floridita Food Truck
Cuban-inspired bites right at the resort, made for long holiday afternoons by the pool.
Pet Friendly Holiday Stays
Your dog doesn’t have to miss the holidays. Havana Cabana welcomes well-behaved dogs up to 50 lbs each, with up to two dogs per room. A pet fee of $75 per night applies for one dog, or $100 per night for two.
Key West Holiday Offers
Make your holiday trip go further with our latest Key West hotel offers, including the Cyber Sale. Book direct to see current rates and offers for your stay.
Moji-toes In the sand
ENJOY A $50 DINING CREDIT PLUS MINI BOTTLE OF RUM AT CHECK-IN!
Slip off your sandals and sip into Key West mode. Stay two nights or more and enjoy a $50 dining credit plus a mini bottle of rum—the perfect recipe for Key West relaxation.
Havana In Advance
IT PAYS TO PLAN AHEAD!
Good things come to those who plan. Lock in your Havana Cabana getaway early and enjoy exclusive savings of up to 25%!
Key West Holiday FAQs
Can we request early check-in or late checkout over the holidays?
Contact the hotel with your arrival and departure details to ask about availability, any fees and when your request can be confirmed.
Can the hotel help us plan Christmas dinner or local activities?
Yes. Our on-site concierge can help with local recommendations and planning. Contact the hotel ahead of your stay to share your plans.
Which room should we book for a Christmas getaway?
For couples, the Luis Premium King Balcony offers a king bed and outdoor space. Friends or families sharing a room may prefer the Luis Premium Two Queens Balcony or the Havana Two Queens Poolside. Our reservations team can help confirm availability and the best fit for your group.
Can we take the hotel shuttle to see the holiday lights?
Yes. Havana Cabana offers a complimentary shuttle to the Historic Seaport, running every half hour, so it is easy to explore the waterfront's holiday lights.
Are the restaurants and bars open on Christmas Day?
Yes. Havana Cabana's restaurants and bars are open on Christmas Day.
When is the Key West Lighted Boat Parade?
The 2026 parade sails through Key West Bight on Saturday, December 12 at 8pm, with festivities along the Harbor Walk from 6pm.
Is Havana Cabana pet friendly over the holidays?
Yes. Well-behaved dogs up to 50 lbs each are welcome, with up to two dogs per room. A pet fee of $75 per night applies for one dog, or $100 per night for two.
